Ozone Reactions with Organic Compounds

Half Title......Page 1
Title......Page 3
Copyright......Page 4
Series Information......Page 5
FOREWORD......Page 6
PREFACE......Page 7
1 
Complexes and Radicals Produced during 
Ozonation of Olefins......Page 10
Visible Spectr......Page 16
Literature Cited......Page 17
2 
Ozonolysis: Formation of Cross Diperoxides......Page 18
Ozonolysis of 2,3-Dimethyl-2-pentene......Page 20
Ozonolysis of 2-Methyl-3-ethyl-2-pentene......Page 21
Preparation of 1,1 -Dimethyl-4,4-diethyl-2,3,4,5 -tetraoxacyclohexane......Page 22
Results and Discussion......Page 23
Literature Cited......Page 29
Preparation of the Ozonides......Page 31
Experimental......Page 32
Configuration of cis-trans Isomeric Ozonide......Page 35
Fragmentation Products......Page 37
Rates of Fragmentation......Page 38
Mechanism of the Solvent Fragmentation of Ozonides......Page 42
Literature Cited......Page 43
4 
Quantitative Investigation of the Ozonolysis 
Reaction......Page 44
Relative Rate Constants......Page 45
Gas Chromatographic Analyses......Page 48
Literature Cited......Page 58
5 
The Interaction of Ozone with Double 
Bonds Containing Vinyl Bromide Moieties......Page 59
Ozonolysis of 2,3-Dibromo-2-butene......Page 63
Stoichiometry of the Reactio......Page 64
Ozonolysis Products.......Page 65
Rationalization of Ozonolysis Products......Page 66
Conclusions......Page 71
Literature Cited......Page 73
6 The Ozone-Hydrosilane Reaction:   A Mechanistic Study......Page 74
Ozone Competition Reaction Procedures.......Page 75
Relative Reactivity and Electronic Considerations.......Page 76
Step A—Association of Ozone with the Silicon Atoms.......Page 79
Step(s) B1 and B2—Hydrogen Abstraction......Page 82
Steps C and D—Th e Nature of the Recombining Fragments.......Page 83
Conclusions......Page 84
Literature Cited......Page 85
7 
The Ozonolysis of Organomercurials......Page 87
The Reaction......Page 89
Procedure......Page 90
OTHER STUDIES......Page 91
Carbon—Carbon Cleavage......Page 92
Intermediate Products from Ozonolysis of Organomercurials......Page 93
Kinetic Studies......Page 94
Ozonolysis Products......Page 98
Intermediates......Page 99
Reaction Stoichiometry......Page 100
Kinetic Studies......Page 101
Mechanism......Page 104
Synthetic Utility......Page 107
Literature Cited......Page 108
8 
Ozonation of p-Nitro-N,N-Dimethylaniline......Page 110
General......Page 111
Ozonation of p-Nitro-2V,2V-dimethylaniline (IVc......Page 112
ACTIVE OXYGEN CONTENT......Page 113
THERMAL DECOMPOSITION......Page 114
Discussion......Page 115
Literature Cited......Page 122
9 
Mechanism of Ozonation Reactions......Page 123
Product Analysis......Page 124
Results......Page 125
Literature Cited......Page 131
INDEX......Page 134