Strategies and Solutions to Advanced Organic Reaction Mechanisms: A New Perspective on McKillop's Problems

Front Matter
Copyright
Dedication
Preface
	The Purpose of Writing This Book
	What This Book Offers
	Organization of Book and Layout of Solutions
	Acknowledgments
	References
The Logic of Organic Reaction Mechanisms
	What is an Organic Chemical Reaction?
	The Balanced Chemical Equation
	What Is Contained in a Reaction Scheme?
	Principle of Conservation of Structural Aspect
	Curly Arrow Notation
	Baeyer-Villiger Oxidation Mechanism
	Table of Recommended Textbooks on Physical Organic Chemistry
	Base Strength and pKA
	Autoxidation
	References
Evidence for Organic Reaction Mechanisms
	What Is Physical Organic Chemistry?
	Experimental Physical Organic Chemistry
	Applying Experimental Techniques-Baeyer-Villiger Oxidation Revisited
	References
Problem Solving Organic Reaction Mechanisms
	Theoretical Problem-Solving Strategy
	Experimental Problem-Solving Strategy
	Case Study: Rearrangement of Cinenic Acid to Geronic Acid
	Current State of Pedagogy and Academic and Future Directions
	References
Solutions 1 - 50
	A Tandem Route to 1,2,3,4-Tetrasubstituted Naphthalenes
		Solution: 1 to 2
		Solution: 2 to 3
		Solution: D to 4
		Balanced chemical equations
		Key Steps Explained
		Additional Resources
		References
	Hydroazulenes by Radical Cyclization
		Solution
		Balanced chemical equation
		Key Steps Explained
		Additional Resources
		References
	Cinnolines to Indoles
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Rearrangement During NMR Studies
		Solution
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Trifluoromethyl Heterocycles
		Solution: 1 to 2
		Solution: 2 to 3
		Solution: 3 to 4
		Balanced chemical equations
		Key Steps Explained
		Additional Resources
		References
	3-Substituted Chromones From Pyranobenzopyrans
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Acid-Catalyzed Rearrangements of 1-Arylindoles
		Solution: 1 to 2
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Unusual Deprotection of an Aryl Ester
		Solution: 2 to 3
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	3,1-Benzoxathiin Formation
		Solution: Mechanism 1
		Solution: Mechanism 2
		Key Steps Explained
		Additional Resources
		References
	Arylacetone Synthesis by Carroll-Type Rearrangement
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	Attempted Knoevenagel Reaction Gives Mannich-Type Products
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 3 to 2
		Balanced Chemical Equation: 3 to 2
		Key Steps Explained
		Additional Resources
		References
	Pyridinium Salt Rearrangements
		Solution: 1 to 2
		Solution: 3 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A Pyridazine From a Thiophene Dioxide
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Biomimetic Synthesis of Litebamine
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 4 to 5
		Solution: 5 to 6
		Balanced Chemical Equation: 5 to 6
		Key Steps Explained
		Additional Resources
		References
	Acid-Catalyzed Degradation of N-Nitroso-2,3-didehydromorpholine
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A New Route to 4-Amino-3-arylcinnolines
		Solution: 2 to 3 (Path a)
		Solution: 2 to 3 (Path b)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Base-Induced Cyclizations of o-Ethynylaryl-Substituted Benzyl Alcohols
		Solution: 1 to 2
		Solution: 3 to 5
		Key Steps Explained
		Additional Resources
		References
	Trifluoromethylpyrroles From Trifluoromethyloxazolones
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The Hooker Oxidation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Synthesis of 1,3-Disubstituted Pyrroles
		Solution: 3 to 4
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Grob Fragmentation of a 1-Azaadamantane
		Solution: 1 to 2
		Balanced Chemical Equation
		Solution: 2 to 3
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Selective Substitution of 3-Methoxypyrazine N-Oxide
		Solution: 1, 2, and 3 to 4 (When ZnBr2 Present)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Reactions of Ethacrylate Esters With NO2BF4
		Solution: 1 to 2
		Solution: A to 3
		Solution: 4 to 5
		Balanced Chemical Equation: 4 to 5
		Solution: C to 6
		Balanced Chemical Equation: 4 to 6
		Key Steps Explained
		Additional Resources
		References
	A Furan Synthesis
		Solution: 1 to 2
		Solution: 2 to 3 (Authors Mechanism)
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Dimerization of Vinca Alkaloids
		Solution
		Key Steps Explained
		Additional Resources
		References
	Nitration of a Quinoline Derivative
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Binaphthyldiquinones
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Heterocyclic Fun With DMAD
		Solution: Mechanism 1
		Solution: Mechanism 2
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Unexpected Formation of a 1,5-Benzodiazonine
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Thiopyran to Thiophene Transformation
		Solution: 1 to 2
		Solution: 3 to 4 (Path a: F to 4)
		Solution: 3 to 4 (Path b: F to 4)
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Skeletal Rearrangements of a Diterpene
		Solution: 1 to 2
		Solution: B to 4
		Solution: 4 to 3
		Solution: 3 to 5
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Reissert Reactions of Quinoxaline N-Oxides
		Solution: 1 to 2
		Solution: 1 to 3
		Solution: 4 to 5
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Unexpected Results in Directed Metalation
		Solution: 3 to 4/5
		Key Steps Explained
		Additional Resources
		References
	1,4-Dioxene in Synthesis
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Collins Oxidation of Phenylethanols
		Solution: 1 to 2
		Solution: 4 to 5
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Allene Sulfoxide Rearrangement
		Solution: 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A Failed ``Pinacol-Type´´ Rearrangement
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Allylation of 1,4-Benzoquinones
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Benzopyrene Synthesis-By Accident
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Rearrangement of Ketene Acetals
		Solution: 2E to 3
		Solution: 2Z to 3
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Nucleophilic Additions to a Heterocyclic o-Quinone
		Solution: 1 to 2
		Solution: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	How Mitomycin C Can Crosslink DNA
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Two Carbon Ring Expansions of Cycloalkanones
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 3 to 4
		Balanced Chemical Equation: 3 to 4
		Solution: 3 to 5
		Balanced Chemical Equation: 3 to 5
		Key Steps Explained
		Additional Resources
		References
	Fulgides: Synthesis and Photochromism
		Solution: 1 and 2 to 3 (Stobbe Condensation)
		Balanced Chemical Equation: 1 and 2 to 3
		Solution: 3 to 4 (Lactone Opening Esterification)
		Balanced Chemical Equation: 3 to 4
		Solution: 4 to 5 (Stobbe Condensation)
		Balanced Chemical Equation: 4 to 5
		Solution: 5 to 6 (Saponification of Diester to Diacid)
		Balanced Chemical Equation: 5 to 6
		Solution: 6 to 7
		Balanced Chemical Equation: 6 to 7
		Solution: 7 to 8 (Base-Assisted Ring Opening Alkylation)
		Balanced Chemical Equation: 7 to 8
		Solution: 8 to 9 (Acetyl Chloride-Assisted Cyclization)
		Balanced Chemical Equation: 8 to 9
		Solution: 9 to 10 (Photochromism Mechanism)
		Key Steps Explained
		Additional Resources
		References
	Benzodiazepines From (R)-(+)-Pulegone
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Furan to Pyran Ring Expansion
		Solution: 1 to 2 (Mechanism 1: Consistent With Deuterium Labeling Study)
		Solution: 1 to 2 (Mechanism 2: Inconsistent With Deuterium Labeling Study)
		Key Steps Explained
		References
	A Structure and Mechanism Correction
		Solution: 1 and 2 to 3 (Claimed Reaction)
		Solution: 3 to 4 (Claimed Reaction)
		Solution: 1 and 2 to 5 (Actual Reaction)
		Solution: 5 to 4 (Actual Reaction)
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Propargylbenzotriazoles to Five-membered Heterocycles
		Solution: 1 and 2 to 3
		Balanced Chemical Equation: 1 and 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equation: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	From Carvone to an Isoxazoloazepine
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Isoxazoles From Cyclopropanes
		Solution: 1 to 2
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
Solutions 51 - 100
	A Radical Cascade From a Ketene Dithioacetal
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Synthesis of 3-Alkyl-1-naphthols
		Solution: 2 to 3
		Solution: 4 to 5
		Solution: 6 to 7
		Key Steps Explained
		Additional Resources
		References
	An Entry to Indole Alkaloids of Unusual Structural Type
		Solution: 1 to 2
		Solution: 2 to 3
		Solution: 3 to 5 and 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Cyclization as a Key Step to Hirsutene
		Solution
		Key Steps Explained
		Additional Resources
		References
	A 1,3-Cyclopentanedione to 1,4-Cyclohexanedione Transformation
		Solution: Originally Proposed Mechanism for 1 to 2
		Solution: Revised Mechanism for 1 to 2 Part 1: 1 to 3
		Solution: Revised Mechanism for 1 to 2 Part 2: 3 to 2
		Key Steps Explained
		Additional Resources
		References
	Conversion of o-Hydroxyaryl Ketones Into 1,2-Diacylbenzenes
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Mechanisms of Bimane Formation
		Solution: 1 to syn-2
		Solution: A and B to anti-2
		Balanced Chemical Equation: 1 to syn-2/anti-2
		Solution: 3 to syn-4
		Balanced Chemical Equation: 3 to syn-4
		Key Steps Explained
		Additional Resources
		References
	A Carbohydrate to Cyclopentanol Conversion
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Balanced Chemical Equation: Scheme 2
		Balanced Chemical Equation: Scheme 3
		Balanced Chemical Equation: Scheme 4
		Additional Resources
		References
	Pyridazines From 1,2,4-Triazines
		Solution: 1 to 2 Using 15N Label on Phenylacetonitrile
		Solution: 2 to 3 Using 15N Label on Phenylacetonitrile
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Natural Product Degradation During Extraction and/or Chromatography
		Solution: Authors Proposal (Ionic Mechanism)
		Solution: Alternative Proposal (Radical Mechanism)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Simple Access to Oxaadamantanes
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: I to 3
		Balanced Chemical Equation: 1 to 3
		Solution: D to 4
		Balanced Chemical Equation: 1 to 4
		Key Steps Explained
		Additional Resources
		References
	A Pyrimidine Rearrangement
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	1,4-Thiazin-3-ones From 1,4-Oxathiins
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Unusual Route to 3-Acylfurans
		Solution: 1 to 2
		Solution: 2 to 3
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Reaction of PQQ With l-Tryptophan
		Solution
		Additional Resources
		References
	An Unexpected Result From an Attempted Double Bischler-Napieralski Reaction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Bis-Indole Alkaloid Formation
		Solution: 1 to 2
		Solution: 3 to 4 and 5
		Solution: 6 to 7 and 8
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Azaphenalene Alkaloid Synthesis: A Key Step
		Solution: Path A
		Solution: Path B (C to 2 Alternative)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Primary Nitroalkane to Carboxylic Acid Transformation
		Solution: 1 to 2
		Solution: 3 to 2
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	α-Diazoketones With Rhodium(II) Acetate
		Solution: 1 to 2
		Solution: E to 3
		Solution: C to J and 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Pyrrolo[1,2-a]benzimidazole Synthesis by Ortho Nitro Interaction
		Solution: 1 to 2
		Solution: H to 3
		Solution: H to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Horner-Wittig Reaction on a Bifuranylidenedione
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Lactone Ammonolysis
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Intramolecular Schmidt Reaction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Indolizidones by Intermolecular Photochemical Reaction
		Solution: 1 to E
		Solution: E to G
		Solution: G to 3 (Author Mechanism)
		Solution: G to 3 (Alternative Proposal)
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	An Unexpected Product From Amine Oxidation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Degradation of Pyripyropene A
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 2 to 3 and 4
		Balanced Chemical Equation: 2 to 3 and 4
		Key Steps Explained
		Additional Resources
		References
	Benzofurans From Cyclobutenediones
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Solution: 4 to 5
		Solution: 5 to 6
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Acid-Catalyzed Condensation of Indole With Acetone
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Synthesis of 2-Formylpyrrolidines
		Solution: 1 to 2
		Solution: 2 to 3
		Balanced Chemical Equation: 2 to 3
		Solution: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	An Abnormal Claisen Rearrangement
		Solution
		Key Steps Explained
		Additional Resources
		References
	Benzoxepinones From Phthalides
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	m-Terphenyls From Pyrones
		Solution: 1 to 2
		Solution: B to 3
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A Cascade Reaction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Photochemical Ortho Rearrangements
		Solution: 1 to 3
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	From Bicycle to Pentacycle to Tricycle
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Lewis Acid-Catalyzed Cyclopropyl Ketone Rearrangement
		Solution
		Key Steps Explained
		Additional Resources
		References
	An Intramolecular Ring Closure
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Photochemical Rearrangement of Pyran-2-ones
		Solution: 1 to 2
		Solution: F to H (Alternative Path)
		Key Steps Explained
		Additional Resources
		References
	A Paclitaxel Rearrangement
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Ionic Diels-Alder Reaction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The Eschenmoser Fragmentation Reaction Extended
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Modified Batcho-Leimgruber Synthesis
		Solution: 1 to 4 p-TsOH Acid Catalysis
		Key Steps Explained
		Additional Resources
		References
	A Pyrone to Pyran Conversion
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Conformationally Rigid 4-Oxoquinolines
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Efficient Chromene Synthesis
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Flash Vacuum Pyrolysis of o-Xylylene Dimers
		Solution: 1 to 2
		Solution: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	Synthesis of a Neocarzinostatin Building Block
		Solution
		Key Steps Explained
		Additional Resources
		References
	Oxazole Esters From α-Amino Acids
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Unexpected Formation of a Phenazine
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
Solutions 101 - 150
	Conversion of Primary Amides Into Nitriles
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Efficient Benzo[b]fluorene Synthesis
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Facile Synthesis of Tetracyclic Pyrroloquinazolines
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Ethyl 2-Chloronicotinate From Acyclic Precursors
		Solution: 1, 2, and 3 to 4
		Solution: 4 to 5
		Balanced Chemical Equation: 1, 2, and 3 to 4
		Balanced Chemical Equation: 4 to 5
		Key Steps Explained
		Additional Resources
		References
	A 2-Arylpropanoic Acid Synthesis
		Solution: 1 to 2
		Solution: 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Isoquinolin-4-ones
		Solution: 1 to 2
		Solution: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	Naphthopyrandione From 1,4-Naphthoquinone
		Solution: 1a to 3
		Solution: 1b to 4
		Balanced Chemical Equations
		Key Steps Explained
		Reference
	A Photochromic Product for Sunglasses
		Solution: 1 to 2
		Solution: 2 to 3
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A Quick Entry to the Aklavinone Ring System
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A ``Stable Enol´´ That Doesnt Exist
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Conversion of an Indole-Based Bicyclo[5.3.1]undecane Into a Bicyclo[5.4.0]undecane
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Classical Mannich Approach to Isoquinoline Alkaloids Leads to an Unexpected Product
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Reaction of Benzothiazole With DMAD
		Solution
		Key Steps Explained
		Additional Resources
		References
	Inhibition of the l-DOPA to l-Dopaquinone Oxidation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A One-Pot Synthesis of 1,3,6,8-Tetramethyl-2,7-naphthyridine
		Solution: Formation of 1 Part 1 (A to H)
		Solution: Formation of 1 Part 2 (H to 1 Path A)
		Solution: Formation of 1 Part 3 (H to 1 Path B)
		Solution: Formation of 1 Part 4 (ALTERNATE ROUTE: B to O1)
		Solution: Formation of 1 Part 5 (ALTERNATE ROUTE: S to H)
		Solution: Formation of 2
		Balanced Chemical Equations
		Key Steps Explained
		References
	Unexpected Course of a Mannich Reaction in Alkaloid Synthesis
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Thioindigo
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Unexpected Reaction During Studies of Amine Oxide Rearrangements
		Solution: 1 to 3 (Expected Product)
		Solution: 1 to 2 (Observed Product)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Unusual Phosphite-Induced Deoxygenation of a Nitronaphthalene
		Solution: 1 to 2 Authors Mechanism
		Solution: 1 to 2 Alternative Mechanism
		Solution: 3 to 2 Authors Mechanism
		Solution: 3 to 2 Alternative Mechanism
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Benzimidazole to Pyrroloquinoxaline Transformation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Acid-Catalyzed Benzophenone Isomerization
		Solution: Hayashi Mechanism1
		Solution: Sandin Mechanism2
		Solution: Wang Mechanism3
		Key Steps Explained
		Additional Resources
		References
	2-Oxabicyclo[1.1.0]butanone Is Not Easily Accessible
		Solution: Authors Mechanism
		Solution: Alternative Mechanism
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Simple Synthesis of the Indole Alkaloid Yuehchukene
		Solution
		Key Steps Explained
		Additional Resources
		References
	Isoquinoline Rearrangement
		Solution
		Key Steps Explained
		Additional Resources
		References
	Multiple Sigmatropic Rearrangements
		Solution: 1 to 2 in PhCl
		Solution: 1 to 2 and 3 in PhCl and AIBN
		Solution: 1 to 3 in pTsOH
		Key Steps Explained
		Additional Resources
		References
	A Vilsmeier-Induced Annulation to Benzene
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Isopropylidene to 2-Alkyne Conversion
		Solution: Corey2 Mechanism
		Solution: Zard4 Mechanism
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A Tryptamine to Pentacyclic Indoline Transformation
		Solution: 1 to 2
		Catalyst Regeneration
		Balanced Chemical Equation: 1 to 2
		Solution: 1 to 3
		Balanced Chemical Equation: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	Ring Contractions of a Dibenzothiepinone
		Solution: 1 to 2
		Solution: 1 to 3
		Solution: 1 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Steroid Fragmentation With DDQ
		Solution: 1 to 2
		Solution: 1 to 3
		Solution: 1 to 4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A Base-Induced Vinylcyclopropane Rearrangement
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	4-Demethoxydaunomycin: The Desired Result, but Not According to Plan
		Solution: 1 to 3
		Solution: 3 to 4
		Solution: 4 to 5
		Solution: 5 to 2
		Key Steps Explained
		Additional Resources
		References
	Three Isomeric Hexadienols Give the Same Bicyclic Lactone
		Solution: 1 to 4
		Solution: 2 to 4
		Solution: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	Degradation of Antibiotic X-537A
		Solution: 2 to 3 and A
		Solution: A to 5
		Balanced Chemical Equation: 2 to 3 and 5
		Solution: 2 to 4
		Solution: D to 6
		Balanced Chemical Equation: 2 to 3 and 6
		Key Steps Explained
		Additional Resources
		References
	Steroid Rearrangements: Appearances Can Be Deceptive
		Solution
		Additional Resources
		References
	Synthesis of Eburna and Aspidosperma Alkaloids
		Solution: 2 to 3a and 3b
		Balanced Chemical Equation: 2 to 3a and 3b
		Solution: 2 to 4 and 5
		Balanced Chemical Equations: 2 to 4 and 5
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Highly Hindered Cyclic Amines
		Solution: 1 to 2
		Solution: 1 to 3
		Balanced Chemical Equations: 1 to 2 and 3
		Solution: 4 to 5 and 6
		Balanced Chemical Equations: 4 to 5 and 6
		Key Steps Explained
		Additional Resources
		References
	A 1,2-Dihydrobenzocyclobutane to Isochroman-3-one Conversion
		Solution
		Key Steps Explained
		Additional Resources
		References
	An Unexpectedly Facile Decarboxylation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Regiospecific Synthesis of a 1,2-Dihydronaphthalene
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Degradation of Terramycin
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Bi-indane-l,3-dione
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Solution: 4 to 5
		Solution: 5 to 6
		Key Steps Explained
		Additional Resources
		References
	A Coumarin to Cyclopentenone Transformation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	``Synthetic Heroin´´ and Parkinsonism
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Rearrangement of 6-Hydroxyprotopine to Dihydrosanguinarine
		Solution
		Key Steps Explained
		Additional Resources
		References
	Biotin Synthesis: Sulfur Preempts a Beckmann Rearrangement
		Solution
		Key Steps Explained
		Additional Resources
		References
	A 1,4-Dithiin to Thiophene Rearrangement
		Solution: 1 to 2
		Solution: 1 to 3
		Balanced Chemical Equation: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	An Intramolecular Wittig Reaction
		Solution: 1 to 2
		Solution: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	Amination of a Cephalosporin
		Solution: 1 to 2
		Solution: 2 to 3
		Key Steps Explained
		Additional Resources
		References
	A Uracil to 1,2,3-Triazole Conversion
		Solution: Authors Mechanism
		Solution: Alternative Mechanism
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
Solutions 151 - 200
	Schumm Devinylation of Vinyl Porphyrins
		Solution: Mechanism 1A
		Solution: Mechanism 1B
		Solution: Mechanism 2A
		Solution: Mechanism 2B
		Solution: Mechanism 3
		Solution: Mechanism 4
		Key Steps Explained
		Additional Resources
		References
	A Uracil to Substituted Benzene Transformation
		Solution: 1 to 2
		Solution: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	γ-Lactones From Vinyl Sulfoxides
		Solution
		Key Steps Explained
		Additional Resources
		References
	Tetrahydrothieno[2,3-c]- and -[3,2-c]pyridine Synthesis
		Solution: 1 to 2 (Weakly Acidic Medium)
		Solution: 1 to 2 and 3 (Strongly Acidic Medium)
		Key Steps Explained
		Additional Resources
		References
	Oxothiolan  Oxathian  Oxothiolan  Oxathian
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 2 to 3
		Balanced Chemical Equation: 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equation: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	A Thiazolopyrimidine to Pyrrolopyrimidine Transformation
		Solution: 1 and 2 to 3
		Balanced Chemical Equation: 1 and 2 to 3
		Solution: 3 to 6 to 5
		Balanced Chemical Equation: 3 to 6 to 5
		Solution: 5 to 4
		Key Steps Explained
		Additional Resources
		References
	Oxidation of 1,5-Diacetoxynaphthalene With NBS
		Solution: 1 to 3 to 2
		Balanced Chemical Equation: 1 to 3
		Balanced Chemical Equation: 3 to 2
		Balanced Chemical Equation: 4 to 2
		Key Steps Explained
		Additional Resources
		References
	Badly Chosen Reaction Conditions?
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	One Step Synthesis of a Highly Symmetrical Hexacyclic System From a Simple Naphthol
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Method for Aryloxylation of p-Cresol
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 2 to 3
		Solution: 2 to 3 Alternative
		Balanced Chemical Equation: 2 to 3
		Solution: 3 to 4
		Balanced Chemical Equation: 3 to 4
		Solution: 3 to 5
		Balanced Chemical Equation: 3 to 5
		Key Steps Explained
		Additional Resources
		References
	Nitriles From N-Chlorosulfonylamides
		Solution: Nitrile Formation Via Triethylamine
		Solution: Nitrile Formation Via Dimethylformamide (DMF)
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Perylenequinone
		Solution
		Balanced Chemical Equation
		Balanced Chemical Redox Equation
		Key Steps Explained
		Additional Resources
		References
	A Route to 2-Vinylindoles
		Solution
		Key Steps Explained
		Additional Resources
		References
	Brain Cancer: The Mechanism of Action of Temozolomide
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Attempted Nef-Type Reaction Leads to 3-Arylpyridine Synthesis
		Solution: Part 1-Reduction
		Solution: Part 2-Rearrangement
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The ArCOMe  ArCCH Transformation
		Solution: 1 to 2
		Balanced Chemical Equation: 1 to 2
		Solution: 2 to 3
		Balanced Chemical Equation: 2 to 3
		Key Steps Explained
		Additional Resources
		References
	β-Amino Nitriles From Azetidones
		Solution
		Key Steps Explained
		Additional Resources
		References
	A New Route to 1,3-Disubstituted Naphthalenes
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Efficient Annulation Route to 6-Substituted Indoles
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Failure of a Rearrangement: From a Useful Compound to a Useless Product
		Solution
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Trisubstituted Isoxazoles
		Solution: 1 to 2 and 2 to 3
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	2,3-Dihydrobenzofurans From 1,4-Benzoquinones
		Solution: 1 and 2 to 3 and 3 to 4
		Solution: 5 and 6 to 7
		Solution: 7 to 8
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Easy Construction of a Tricyclic Indole Related to the Mitomycins
		Solution: 1 to 2
		Solution: 2 to 3
		Key Steps Explained
		Additional Resources
		References
	Cycloaddition to a Benzothiopyrylium Salt
		Solution: 3 to 4
		Solution: 3 to 5
		Key Steps Explained
		Additional Resources
		References
	Benzotriazole From 1,2,4-Benzotriazine N-Oxides
		Solution: 1 to 3
		Solution: 2 to 3
		Key Steps Explained
		Additional Resources
		References
	A Furan  Furan Transformation
		Solution
		Key Steps Explained
		Additional Resources
		References
	Ring Expansion of Both Rings of Penicillin Sulfoxides
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Retro-Pictet-Spengler Reaction
		Solution: Epimerization Mechanism 1 (C1N2 Bond Scission)
		Solution: Epimerization Mechanism 2 (Olefin Protonation)
		Solution: Epimerization Mechanism 3 (Iminium Ion Formation)
		Solution: Degradation Mechanism 1 (Retro-Pictet-Spengler) Path A
		Solution: Degradation Mechanism 1 (Retro-Pictet-Spengler) Path B
		Key Steps Explained
		Additional Resources
		References
	An Olefin to α-Hydroxy Ketone Transformation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Benzofuran From a Cyclopropachromone
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Pyridocarbazole to Pyridazinocarbazole Rearrangement
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Substituent Group Effect During Sulfide  Sulfoxide Oxidation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Ring Contraction of a Benzodiazepine
		Solution: Mechanism 1A (Authors Mechanism)
		Solution: Mechanism 1B (Authors Mechanism)
		Solution: Mechanism 2 (Alternative Mechanism)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Indane-1,3-dione Synthesis
		Solution: Mechanism 1 (Mosher and Meier)
		Solution: Mechanism 2 (Alternative)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Azepine to Cyclohexadienone Ring Contraction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Xanthopterin From Pterin 8-Oxide
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Fused Dihydro-l,4-dithiins From Chromanones
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The ``Additive Pummerer Reaction´´
		Solution: 1 to 3
		Solution: 1 to 4
		Key Steps Explained
		Additional Resources
		References
	An Illustration of the Problem of Artifacts in Natural Product Chemistry
		Solution
		Key Steps Explained
		Additional Resources
		References
	Vinylogy, and a Stereochemical Puzzle
		Solution: Mechanism 1 (Kiehlmann et al.)
		Balanced Chemical Equation: Mechanism 1
		Solution: Mechanism 2 (Acevado et al.)
		Balanced Chemical Equation: Mechanism 2
		Key Steps Explained
		Additional Resources
		References
	A Simple, High Yielding Route to a Cage Compound
		Solution: 1 to 2
		Solution: 1 to 3
		Key Steps Explained
		Additional Resources
		References
	Not All Ketals Hydrolyze Easily in the Expected Manner
		Solution: 1 to 2
		Solution: 1 to 2 and 3
		Key Steps Explained
		Additional Resources
		References
	From a Tricycle to a Ring Expanded Bicycle
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Flavone From a Chromanone
		Solution: 1 to 2
		Solution: 2 to 3 (at Elevated Temperature)
		Solution: 2 to 4 (at Elevated Temperature NO Added Base)
		Solution: 1 to 4 (With Added Base)
		Key Steps Explained
		Additional Resources
		References
	Thiophene Ylide Rearrangement
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Stepwise 2π+2π Intermolecular Cycloaddition
		Solution
		Key Steps Explained
		Additional Resources
		References
	Rearrangement of an Aryl Propargyl Ether
		Solution
		Key Steps Explained
		Additional Resources
		References
	The Best Laid Plans
		Solution: 1 to 2 (Expected Result) Step 1
		Solution: 1 to 2 (Expected Result) Step 2
		Solution: 1 to 3 (Observed Result)
		Alternative Pathway From Intermediate D
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	A New Synthesis of Substituted Ninhydrins
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Thermal Elimination Reactions Often Fail
		Solution
		Key Steps Explained
		Additional Resources
		References
Solutions 201 - 250
	The Wrong Choice of Reaction Conditions? How Not to Prepare an Acid Chloride
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Quantitative Yield Isomerization of a Xylenol Derivative
		Solution
		Key Steps Explained
		Additional Resources
		References
	and an Alternative Route to the Starting Material for Problem 202
		Solution: 1 to 2
		Solution: 1 to A
		Solution: A to 2
		Key Steps Explained
		Additional Resources
		References
	Hydride-Induced Rearrangements With Indole Alkaloid Intermediates
		Solution
		Balanced Chemical Equation
		Work-Up Reaction
		Key Steps Explained
		Additional Resources
		References
	An Unusual ``Hydrolysis´´ Product of 2-Nitrosopyridine
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Quinolizine to Indolizine Transformation
		Solution: 1 to A
		Solution: A to 2
		Key Steps Explained
		Additional Resources
		References
	SNHetAr Reactions Often Proceed With Complications
		Solution: 1 to 2 (ipso Substitution)
		Solution: 1 to 3 (tele Substitution)
		Solution: 1 to 4 (ANRORC Mechanism)
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Rearrangement During Recrystallization
		Solution: 1 and 2 to 3
		Solution: 3 to 4
		Solution: 4 to 5
		Balanced Chemical Equation (4 to 5)
		Key Steps Explained
		Additional Resources
		References
	Another Attempt to Reduce a Ketone Goes Wrong
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A More Complex Benzocyclobutane to Isochroman-3-one Rearrangement (c.f. Problem 138)
		Solution
		Key Steps Explained
		Additional Resources
		References
	Indoles by Solvometalation Ring Closure
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	An Unusual-But Inefficient-Synthesis of Methyl 1-Hydroxynaphthalene-2-carboxylate
		Solution: Mechanism A
		Solution: Mechanism B
		Solution: Mechanism C
		Key Steps Explained
		Additional Resources
		References
	Synthesis of α-Arylalkanoic Acids From Acetophenones
		Solution: B to C
		Solution: C to D
		Solution: D to 2
		Key Steps Explained
		Additional Resources
		References
	Triazene-Triazole-Triazole Interconversions
		Solution: 1 to 2 to 3
		Key Steps Explained
		Additional Resources
		References
	Reissert Compounds as Precursors to Novel Phthalides
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Di-t-butylacetylene Does Not Cycloadd to 2-Pyrone
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Failed Thorpe-Dieckmann Cyclization: ``Obvious´´ Reactions Are Not Always Well Behaved
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	and Can Lead to Remarkable Rearrangements: A Failed Thorpe-Ziegler Cyclization
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Remarkably Stable Tertiary Alcohol by Solvolysis of a Primary Tosylate
		Solution: Mechanism A-Bornyl Path (Helicopter View)
		Solution: Mechanism B-Fenchyl Path (Helicopter View)
		Key Steps Explained
		Additional Resources
		References
	``Anionic Activation´´ for the Preparation of Fluoroheterocycles
		Solution: 1 to 2 Via Phenylacetylene
		Balanced Chemical Equation: 1 to 2 Via Phenylacetylene
		Solution: 1 to 2 Via Acetophenone
		Balanced Chemical Equation: 1 to 2 Via Acetophenone
		Solution: 3 to 4
		Balanced Chemical Equation: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	Synthesis of a 5-(2-Quinolyl)pyrimidine
		Solution: B to C
		Balanced Chemical Equation: B to C
		Key Steps Explained
		Additional Resources
		References
	``Obvious´´ and ``Nonobvious´´ Pathways to a Highly Substituted Pyridine and Aniline
		Solution: Formation of 3
		Balanced Chemical Equation for Formation of 3
		Solution: Formation of 4 Obvious Pathway
		Balanced Chemical Equation for Formation of 4 Obvious Pathway
		Solution: Formation of 4 Nonobvious Pathway
		Balanced Chemical Equation for Formation of 4 Nonobvious Pathway
		Key Steps Explained
		Additional Resources
		References
	A 1-Isoquinolone Synthesis
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Selective Cleavage of the Mycinose Sugar From the Macrolide Antibiotic Tylosin
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Unexpected Formation of an Enamide
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Highly Functionalized Furans From 3-Bromochromone
		Solution
		Key Steps Explained
		Additional Resources
		References
	A One-Pot Benzene  Naphthalene Transformation
		Solution
		Key Steps Explained
		Additional Resources
		References
	Vicarious Nucleophilic Substitution Routes From Simple to Complex Phenols
		Solution: Formation of 1
		Solution: Formation of 2 (Mechanism Version 1)
		Solution: Formation of 3 (Mechanism Version 2)
		Solution: Formation of 4 (Mechanism Version 3)
		Key Steps Explained
		Additional Resources
		References
	Lewis Acid-Catalyzed Rearrangement of Humulene 8,9-Epoxide
		Solution
		Key Steps Explained
		Additional Resources
		References
	From a Dihydrofuran to an Indole-3-acetate
		Solution: Formation of 1
		Solution: Formation of 2
		Key Steps Explained
		Additional Resources
		References
	Reaction of Fervenulin 4-Oxide With DMAD: The Role of Solvent
		Solution: 1  2
		Solution: 1  3
		Solution: 1  4
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Rearrangement of 4-Quinazolinylhydrazines
		Solution: Rearrangement Under Neutral pH
		Solution: Hydrolysis Under Acidic pH
		Solution: Hydrolysis Under Basic pH
		Key Steps Explained
		Additional Resources
		References
	A Failed Approach to the Oxetan-3-one System
		Balanced Chemical Equations
		Additional Resources
		References
	Tricyclics From Furfural
		Solution: Furfural to 2
		Solution: 2 to 3
		Solution: 3 to 4
		Solution: 4 to 5
		Solution: 5 to 6
		Key Steps Explained
		Additional Resources
		References
		Further Reading
	An Ylide-Based Synthesis of 4-Phenylisocoumarin
		Solution: 1  2
		Solution: 2  3
		Balanced Chemical Equations
		Key Steps Explained
		Additional Resources
		References
	Model Studies for Mitomycin A Synthesis Lead to a New Preparation of Pyrroloindoles
		Solution: 1  2
		Solution: 1  3
		Solution: 1  4
		Key Steps Explained
		Additional Resources
		References
	Formation of N-Cyanofluoren-9-imine From 9-Dinitromethylenefluorene
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Methylphenylacetic Acids From Butenolides
		Solution: 1  2
		Solution: 3  4
		Key Steps Explained
		Additional Resources
		References
	Base-Induced Quinoline Rearrangements
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The Angucyclines: Rearrangement of Angular to Linear Tetracycles
		Solution
		Key Steps Explained
		Additional Resources
		References
	1,2-Dihydropyridines From 2,3-Dihydro-4-pyridones
		Solution
		Key Steps Explained
		Additional Resources
		References
	The Vitamin K to Vitamin K Oxide Transformation
		Solution: Mechanism 1
		Solution: Mechanism 2
		Key Steps Explained
		Additional Resources
		References
	Rearrangement During Intramolecular Cyclization to the Indole 4-Position
		Solution
		Key Steps Explained
		Additional Resources
		References
	4-Quinolone Antibacterials: A New Synthesis
		Solution: 1 to 2
		Solution: 2 to 3
		Solution: 3 to 4
		Key Steps Explained
		Additional Resources
		References
	An Efficient Synthesis of Fused 1,3-Dithiol-2-ones
		Solution
		Key Steps Explained
		Additional Resources
		References
	The ``Double Functional Group Transformation´´: Terminally Unsaturated Nitriles From 1-Nitrocycl ...
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Lewis Acid-Catalyzed Condensation of Indole With 1,3-Cydohexanedione
		Solution: Formation of 1
		Solution: Formation of 2
		Key Steps Explained
		Additional Resources
		References
	Serendipitous Preparation of a Pyrrole Precursor to Porphyrins
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Chromone Ring Contraction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Simple Conversion of Hydroquinone to a Benzofuran, but Which Mechanism?
		Solution: Mechanism 1 (C-Alkylation-Lactonization)
		Solution: Mechanism 2 (O-Alkylation-Michael-Lactonization)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
Solutions 251 - 300
	A Remarkable Loss of One Carbon Atom in the Indole Alkaloid Field
		Solution
		Solution-Possibility 1 (With Intervention of Retro-Mannich Process)
		Solution-Possibility 2 (Without Intervention of Retro-Mannich Process)
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A ``Nonobvious´´ Cycloaddition Reaction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	More Radical Cascades and a Formal [2+2+2] Cycloaddition of a Dienyne
		Solution
		Key Steps Explained
		Additional Resources
		References
	LTA-Induced Acetoxylation and Rearrangement of a Phenol
		Key Steps Explained
		Solution
		Balanced Chemical Equation
		Mechanism for 3
		Additional Resources
		References
	How Cocaine Decomposes at 550C
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Highly Efficient Anilide to Benzimidazole Transformation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The Baeyer-Drewson Synthesis of Indigo
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	The Marschalk Reaction
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A 1,3-Cyclohexanedione to 2-Cyclohexenone Conversion
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Reaction of a Steroidal Olefin With Br2/AgOAc
		Key Steps Explained
		Solution
		Balanced Chemical Equation
		Additional Resources
		References
	A Most Unusual Synthesis of Tropones From Phenols
		Solution: 1 to 2
		Solution: 3 to G
		Solution: G to 4
		Balanced Chemical Equation: G to 4
		Key Steps Explained
		Additional Resources
		References
	Side-Chain Manipulation With a Purine Derivative: Unexpected Formation of a Thietane
		Solution
		Key Steps Explained
		Additional Resources
		References
	An Isoxazoline to Pyridine N-Oxide Transformation
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Simple Synthesis of the Lignan Carpanone
		Solution
		Key Steps Explained
		Additional Resources
		References
	Cyclopentaquinolines by Tandem Reactions
		Solution
		Experimental Results and Verification
		Additional Resources
		References
	Epimerization of Herqueinone
		Solution: Brooks Mechanism
		Solution: Proposed Mechanism
		Key Steps Explained
		Additional Resources
		References
	A New Method for Amide Bond Formation
		Solution
		Key Steps Explained
		Additional Resources
		References
	A Benzothiazole From Oxidation of Mammalian Red Hair With Hydrogen Peroxide
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Cyclopentenones From 1,3-Cyclopentanediones
		Solution: 12
		Solution: C3
		Key Steps Explained
		Additional Resources
		References
	A New Synthesis of 1- and 2-Chloronaphthalenes by an Annulation Process
		Solution: 1  2
		Solution: 3  4
		Key Steps Explained
		Additional Resources
		References
	From the Diterpene Carnosol to the Benzodiazepine Agonist Miltirone
		Solution: 1A
		Solution: A2a
		Solution: A2b
		Balanced Chemical Equation: 12a
		Solution: 2b3
		Solution: 34
		Balanced Chemical Equation: 12b
		Balanced Chemical Equation: 2b3
		Balanced Chemical Equation: 34
		Key Steps Explained
		Additional Resources
		References
	Synthesis of Chiral Phthalimidine Derivatives
		Solution: Synthesis of 1
		Solution: Synthesis of 1: Pathway A
		Solution: Synthesis of 1: Pathway B
		Solution: Synthesis of 2
		Balanced Chemical Equation for the Synthesis of 1
		Key Steps Explained
		Additional Resources
		References
	Remarkable Rearrangement of a Camphor Derivative
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	A Failed Attempt to Prepare Benzylidenethiophthalide by the ``Obvious´´ Method
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Base-Catalyzed Reactions of Highly Hindered Phenols Used as Antioxidants
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Oxidative Rearrangement of an Aconitine Derivative
		Solution: 1 to 2
		Balanced Redox Chemical Equation for 1 to 2
		Solution: 2 to 3
		Balanced Chemical Equation for 2 to 3
		Key Steps Explained
		Balanced Chemical Equation for Hydroxydiphenylacetaldehyde to Benzophenone Transformation
		Additional Resources
		References
	Decomposition of Akuammicine
		Solution: Decomposition at 100C
		Solution: Decomposition at 140C
		Balanced Chemical Equation: Decomposition at 100C
		Balanced Chemical Equation: Decomposition at 140C
		Key Steps Explained
		Additional Resources
		References
	Extending the Favorskii Reaction
		Solution: 12
		Solution: 13
		Solution: 14
		Balanced Chemical Equation: 12
		Balanced Chemical Equation: 13
		Balanced Chemical Equation: 14
		Key Steps Explained
		Additional Resources
		References
	Dihydroxylation/Base Treatment of the Westphalen Ketone
		Solution: 1A
		Balanced Chemical Equation: 1A
		Solution: A2
		Solution: B3
		Balanced Chemical Equation: A2
		Balanced Chemical Equation: 23
		Key Steps Explained
		Additional Resources
		References
	Quantitative Conversion of a Vinylogous Thioamide Into a Thiophene
		Solution: Possibility 1: Sulfonium Ion Intermediate
		Solution: Possibility 2: Iminium Ion Intermediate
		Solution: Possibility 3
		Key Steps Explained
		Additional Resources
		References
	Rearrangements During Synthetic Studies on Carba-Sugars
		Solution: (i) 23 With Triflic Anhydride
		Solution: (ii) Dihydroxylation Mechanism
		Balanced Chemical Equation: Dihydroxylation of 4
		Solution: (ii) Formation of 6
		Solution: (ii) Formation of 5
		Key Steps Explained
		Additional Resources
		References
	A Pyrimidine to Pyrazole Transformation
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Attempted Diastereocontrol in Synthesis of a Homoallylic Alcohol
		Solution
		Key Steps Explained
		Additional Resources
		References
	Arsonium Ylides for Cyclopropane Synthesis
		Solution
		Alternate Possible Pathway
		Key Steps Explained
		Additional Resources
		References
	Pyridoacridines From 4-Quinolones
		Solution: 1 to 2
		Balanced Chemical Equation: 12
		Solution: F to 3
		Balanced Chemical Equation: 13
		Solution: CAN Oxidation of 24
		Balanced Chemical Equation: 24
		Solution: CAN Oxidation of 34
		Balanced Chemical Equation: 34
		Additional Resources
		References
		Further Reading
	Imidoyl Radicals in a New Quinoline Synthesis
		Solution-1 to B
		Solution-B to 2
		Solution-B to 3
		Key Steps Explained
		Additional Resources
		References
	Electrolytic Fluorinative Ring Expansion Reactions
		Solution
		Key Steps Explained
		Additional Resources
		References
	An Isoxazole to 1,3-Oxazine Transformation
		Key Steps Explained
		Solution: 3-Phenyl-5-isoxazolone  1
		Solution: 1  2
		Additional Resources
		References
	Synthesis of Folate Antimetabolites: A Furan to Pyrrole Transformation
		Solution: Mechanism A
		Solution: Mechanism B
		Balanced Chemical Equation (Applies to Both Mechanism A and B)
		Key Steps Explained
		Additional Resources
		References
	Rearrangement of a Silylacetylenic Ketone
		Solution
		Key Steps Explained
		Additional Resources
		References
	And More Silyl Rearrangements: A Brook-Retro-Brook Sequence
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Two Syntheses of Dehydrorotenone
		Solution: (i) From 21
		Balanced Chemical Equation for (i)
		Solution: (ii) From 3 and 42 Mechanism A
		Balanced Chemical Equation for Mechanism A
		Solution: (ii) From 3 and 42 Mechanism B
		Balanced Chemical Equation for Mechanism B
		Key Steps Explained
		Additional Resources
		References
	Radical-Induced Decarboxylation of a Lactone
		Solution: Pathway A
		Pathway B
		Key Steps Explained
		Additional Resources
		References
	Aryl Azide Thermolysis: ``A Series of Rather Involved Rearrangement Reactions´´
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Balanced Chemical Equation
		Balanced Chemical Equation
		Additional Resources
		References
	An Efficient Route to Hexakis(trifluoromethyl)cyclopentadiene
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Exploitation of the Boulton-Katritzky Rearrangement: Synthesis of 4,4-Diamino-3,3-bifurazan
		Solution
		Additional Resources
		References
	Rearrangement During Hydrolysis of a Cyclohexadienone
		Solution: 12
		Balanced Chemical Equation: 12
		Solution: 23, 4
		Balanced Chemical Equation: 13, 4
		Key Steps Explained
		Additional Resources
		References
	Less Common Sigmatropic Rearrangements: [3,4], [3,5], or Even [2,3]?
		Solution: Thionation Mechanism
		Solution: A2
		Balanced Chemical Equation: 12
		Solution: B3
		Balanced Chemical Equation: 13
		Key Steps Explained
		Additional Resources
		References
	Failure to Construct an Oxetane by SN Rearrangement
		Solution
		Balanced Chemical Equation
		Key Steps Explained
		Additional Resources
		References
	Acid-Catalyzed Isomerization of a Tetraspiroketone
		Solution: 12
		Solution: 13
		Key Steps Explained
		Additional Resources
		References
Index
	A
	B
	C
	D
	E
	F
	G
	H
	I
	J
	K
	L
	M
	N
	O
	P
	Q
	R
	S
	T
	U
	V
	W
	X
	Y
	Z