Comprehensive Organic Functional Group Transformations II: v. 6(Carbon with Three or Four Attached Heteroatoms )

Cover Page......Page 1
Book Info......Page 2
Editors-in-Chief......Page 3
Editor of Volume 2......Page 5
Editor of Volume 4......Page 6
Editor of Volume 6......Page 7
Preface......Page 8
Introduction to Volume 6......Page 9
Explanation of the reference system......Page 10
Journal Abbreviations......Page 11
Techniques/Conditions......Page 13
Reagents, Solvents, etc.......Page 14
Part II: Tetracoordinated Carbon with Four Attached Heteroatoms CX1X2X3X4......Page 17
Part III: Tricoordinated Carbon with Three Attached Heteroatoms Y=CX1X2......Page 18
General Methods......Page 19
Additions initiated by free radicals, heat, or radiation......Page 20
Additions catalyzed by salts and complexes of transition metals......Page 22
Conversion of groups attached to an aromatic ring into the trifluoromethyl group......Page 23
Substitution of hydrogen by trifluoromethyl group acting as an electrophile......Page 24
Substitution of halogen by trifluoromethyl group using derivatives of metals......Page 25
Halogen exchange......Page 26
Conversions of other groups to the trifluoromethyl group......Page 27
Transfer of trifluoromethyl groups as radicals......Page 28
Reactions involving trifluoromethyl derivatives of metals and metalloids......Page 29
Transfer of the trichloromethyl group to an aliphatic center......Page 34
Tribromomethyl Derivatives, R-CBr3......Page 35
Mixed Haloforms, CHXY2 and CHXYZ......Page 36
References......Page 37
Biographical sketch......Page 40
6.02 Functions Containing Halogens and Any Other Elements......Page 41
From ethers......Page 42
From dihaloethers......Page 43
From carbonyl derivatives......Page 45
From haloalkenes......Page 46
From mixed haloalkanes......Page 48
From other compounds......Page 49
Tetracoordinated carbon atom bearing mixed halogens and one oxygen function (R1CHal2OR2)......Page 50
Halogen and Sulfur Derivatives (R1CHal2SR2 and R1CHal(SR2)2)......Page 51
From sulfides......Page 52
From halofluoroalkanes and derivatives......Page 58
From alpha,alpha-dichloroalkyl sulfides......Page 60
From tri- or tetrahalomethanes......Page 61
From alkenes......Page 63
From alpha-fluoroalkyl sulfoxides......Page 66
Tetracoordinated carbon atoms bearing mixed halogens and one sulfur function (R1CHal2SR2)......Page 67
From difluoroiodoalkane, bromodifluoroalkane, or chlorodifluoroalkane derivatives......Page 68
From 1,1-difluoroalkene derivatives......Page 69
Halogen and Mixed Chalcogen Derivatives (R1CHal(OR2)(SR3))......Page 70
From imines......Page 71
From amines or hydroxylamines......Page 72
From amides and thioamides......Page 73
From haloiminium salts......Page 75
From haloalkenes and haloalkanes......Page 76
Tetracoordinated carbon atoms bearing one halogen and two nitrogen functions......Page 77
Tetracoordinated carbon atoms bearing one halogen, one nitrogen, and one oxygen function......Page 79
From haloalkanes......Page 80
Tetracoordinated carbon atoms bearing two halogens and one arsenic function......Page 81
Substitution of silanes by haloalkyl derivatives......Page 82
Halogen and Magnesium Derivatives......Page 83
Halogen and Cadmium Derivatives......Page 84
Halogen and Tin Derivatives......Page 85
Halogen and Cobalt or Nickel Derivatives......Page 86
References......Page 87
Biographical sketch......Page 92
6.03 Functions Containing Three Chalcogens (and No Halogens)......Page 93
Ortho-esters from 1,1,1-trihaloalkanes, alpha,alpha-dihaloethers and alpha-haloacetals......Page 94
Ortho-esters from carboxylic acids and derivatives......Page 95
Ortho-esters from dioxacarbenium salts......Page 98
Ortho-esters from ortho-carbonate esters and trialkoxyacetonitriles......Page 99
Trans-esterification reactions......Page 100
Modification of R1 and R2 of R1C (OR2)3......Page 101
From alpha-halodithioacetals and alpha,alpha-dihalothioethers......Page 102
Trithio-ortho-esters from dithioacetals......Page 103
Trithio-ortho-formates from trithiocarbonates......Page 104
Miscellaneous......Page 106
Alkylation with alkyl halides or triflates......Page 107
Reaction with aldehydes and ketones......Page 108
Reaction with alpha,beta-unsaturated ketones or esters......Page 109
Reaction with carboxylic derivatives......Page 110
Modification of R1 and R2 of R1C (SR2)3......Page 111
Oxidized trithio-ortho-esters containing at least one sulfoxide group......Page 112
Oxidized trithio-ortho-esters containing at least one sulfone group......Page 113
Oxidized trithio-ortho-esters containing at least one sulfonate group......Page 115
From ortho-esters......Page 116
From dithioesters......Page 117
From R1C(X1)(X2)X3......Page 118
From ketene dithioacetals......Page 119
From dithioacetals......Page 123
References......Page 124
Biographical sketch......Page 128
Functions Containing Chalcogen and a Group 15 Element......Page 129
From sp3-carbon compounds......Page 130
From sp2-carbon compounds......Page 132
Cycloaddition methods......Page 133
From sp2-carbon compounds......Page 137
Cycloaddition methods......Page 139
Functions bearing one oxygen, one selenium, and one nitrogen substituent......Page 140
From sp2-carbon compounds......Page 142
From sp2-carbon compounds......Page 145
Functions bearing selenium and nitrogen substituent......Page 149
Functions bearing two oxygen and one phosphorus substituent......Page 150
Functions bearing one oxygen and two phosphorus substituents......Page 153
Functions bearing one oxygen, one nitrogen, and one phosphorus substituent......Page 155
Functions bearing one oxygen, one sulfur, and one phosphorus substituent......Page 156
Functions bearing two sulfur and one phosphorus substituent......Page 157
Functions bearing one sulfur and two phosphorus substituents......Page 159
Functions bearing one sulfur, one nitrogen, and one phosphorus substituent......Page 160
Functions bearing one selenium, one sulfur, and one phosphorus substituent......Page 161
Functions bearing two oxygen and one silicon substituent(s)......Page 162
Functions bearing one oxygen and two silicon substituents......Page 163
Functions bearing one oxygen, one sulfur, and one silicon substituent......Page 164
Functions bearing one oxygen, one silicon, and one nitrogen substituent......Page 165
Functions bearing two sulfur and one silicon substituent(s)......Page 166
Functions bearing one sulfur, one silicon, and one nitrogen substituent......Page 168
Functions bearing one oxygen, one sulfur, and one germanium substituents......Page 169
Functions bearing sulfur, oxygen, and a metal......Page 170
Functions bearing two sulfurs and a metal......Page 171
References......Page 172
Biographical sketch......Page 177
6.05 Functions Containing at Least One Group 15 Element (and No Halogen or Chalcogen)......Page 179
1,1,1-Triaminoalkanes......Page 180
1,1,1-Trinitroalkanes......Page 184
1-Amino-1,1-dinitroalkanes......Page 186
Functions Bearing Three Phosphorus Atoms......Page 189
Functions Bearing Three Arsenic Atoms......Page 193
Functions bearing two nitrogen atoms and one arsenic atom......Page 194
Functions bearing two phosphorus atoms and one nitrogen atom......Page 195
Functions bearing two phosphorus atoms and one antimony atom......Page 198
Functions bearing two nitrogen atoms and one boron atom......Page 199
Functions bearing two nitrogen atoms and one indium atom......Page 202
Functions two phosphorus atoms and one gallium atom......Page 205
Functions bearing two phosphorus atoms and one indium atom......Page 206
Functions bearing two nitrogen atoms and one germanium atom......Page 207
Functions bearing two phosphorus atoms and one silicon atom......Page 208
Functions bearing two phosphorus atoms and one germanium atom......Page 209
Functions bearing two phosphorus atoms and one tin atom......Page 210
Functions bearing one nitrogen atom, one phosphorus atom, and one silicon atom......Page 211
Functions Bearing One Nitrogen Atom and Two Silicon Atoms......Page 212
Functions Bearing One Phosphorus Atom and Two Silicon Atoms......Page 213
Functions Bearing One Antimony Atom and Two Silicon Atoms......Page 215
Functions Bearing One Antimony Atom, One Gallium Atom, and One Silicon Atom......Page 217
References......Page 218
Biographical sketch......Page 221
Introduction......Page 223
Functions bearing three silicons......Page 224
Trisilylmethanes and their linear C-organyl derivatives, (X3Si)3CR......Page 225
Functionalized trisilylmethanes containing an \"active\" ligand framework......Page 228
Compounds with an Si3C function as part of one or more ring systems......Page 230
Functions bearing three borons......Page 232
Methanetriboronic esters......Page 234
Tris(boryl)alkanes and boracycloalkanes involving a B3C function......Page 236
Functions bearing three germaniums......Page 238
Synthesis based on alpha-silyl-, boryl-, or germyl-substituted organometallics......Page 239
Synthesis based on ppi-bonded low-coordinate boron and germanium derivatives......Page 240
Intermolecular C-H insertions and cyclization reactions involving a stable germylene......Page 241
Miscellaneous......Page 243
Functions bearing silicon(s) and metal(s)......Page 244
Metal-halogen exchange......Page 245
Synthesis via (cyclo)addition to stannaethenes......Page 246
Transmetallation reactions......Page 247
Functions bearing mixed metalloid(s) and metal(s)......Page 250
Three Similar Metals......Page 253
Three Dissimilar Metals......Page 255
References......Page 256
Biographical sketch......Page 260
6.07 Functions Containing Four Halogens or Three Halogens and One Other Heteroatom Substituent......Page 261
Bromotrifluoromethane......Page 262
Tribromoiodomethane......Page 263
Dichlorodifluoromethane......Page 264
Difluorodiiodomethane......Page 265
Chlorodifluoromethanol......Page 266
Trihalomethyl ethers, CHal3OR......Page 267
Trihalomethyl hypohalites, CHal13OHal2......Page 268
Trihalomethanethiols, CHal3SH......Page 269
Trihalomethyl sulfides, CHal3SR......Page 270
Trihalomethyl sulfoxides and trihalomethyl sulfones, CHal3S(=O)nR......Page 271
Trihalomethanesulfenyl, -sulfinyl, and -sulfonyl halides, CHal13S(=O)nHal2......Page 272
Trihalomethanesulfenic, -sulfinic, and -sulfonic derivatives, CHal3S(=O)nZR......Page 274
(Trihalomethyl) selenium compounds, CHal3SeR......Page 275
Tertiary trihalomethylamines......Page 276
N-(Trihalomethyl)hydroxylamines, CHal3NR1OR2; trihalonitrosomethanes CHal3NO, trihalonitromethanes, CHal3NO2, and related compounds......Page 277
Three halogens and a phosphorus function......Page 278
Three halogens and a silicon function......Page 279
Three halogens and a germanium function......Page 280
(Trihalomethyl)zinc, -cadmium, and -mercury compounds, CHal3MR (M=Zn, Cd,Hg(II))......Page 281
References......Page 282
Biographical sketch......Page 287
6.08 Functions Containing Two Halogens and Two Other Heteroatom Substituents......Page 289
Difluoro compounds......Page 290
Difluoro compounds......Page 292
Dichloro, dibromo, and diiodo compounds......Page 295
Two Halogens and Other Chalcogen Functions......Page 296
Oxygen compounds......Page 297
Two Halogens, a Chalcogen, and Other Functions......Page 298
Cyclic compounds......Page 299
Bis(phosphonates)......Page 300
Cyclic compounds......Page 302
Miscellaneous compounds......Page 303
Two Halogens, a Nitrogen, and a Phosphorus Function......Page 305
Two Halogens, a Phosphorus, and a Metalloid or Metal Function......Page 306
Two Halogens, a Nitrogen, and a Metalloid Function......Page 307
Linear carbosilanes......Page 308
Cyclic carbosilanes......Page 309
References......Page 310
Biographical sketch......Page 312
6.09 Functions Containing One Halogen and Three Other Heteroatom Substituents......Page 313
One halogen and three sulfur functions......Page 314
One Halogen, Two Sulfurs, and a Phosphorus Function......Page 316
One halogen, one sulfur, and two nitrogen functions......Page 317
Miscellaneous halonitromethanes......Page 318
One Halogen and Three Phosphorus Functions......Page 319
Three silicon functions......Page 320
One Halogen, Two Metalloids, and One Metal Function......Page 321
References......Page 322
Biographical sketch......Page 323
Four oxygen functions......Page 325
Four sulfur functions......Page 327
Four selenium functions......Page 328
Triselenium- or tritellurium-substituted methyl chalcogens......Page 329
Methanes Bearing Three Oxygens and a Group 15 Element, Metalloid, or Metal Function......Page 330
Methanes Bearing Three Dissimilar Chalcogens and a Group 15 Element, Metalloid, or Metal Function......Page 331
References......Page 332
Biographical sketch......Page 333
6.11 Functions Containing Two or One Chalcogens (and No Halogens)......Page 335
Compounds with the O2CN2 core......Page 336
Compounds with the S2CN2 core......Page 338
Compounds with the S2CSi2 core......Page 340
Compounds with the S2CGe2 core......Page 341
Compounds with the S2CNP core......Page 342
Compounds with the S2CPMo core......Page 343
Compounds with the S2CPRe core......Page 347
Compounds with the S2CPCo core......Page 348
Compounds with the S2CFe2 core......Page 349
Compounds with the Se2CSiLi core......Page 350
Compounds with the OSCSi2 core......Page 351
Compounds with the SSeCSiLi core......Page 352
Compounds with the OCN3 core......Page 353
Compounds with the OCNP2 core......Page 354
Compounds with the OCNSiTa core......Page 355
Compounds with the OCCo3 core......Page 356
Compounds with the OCNi3 core......Page 357
Compounds with the OCOs3 core......Page 358
Compounds with the OCFe2Rh core......Page 359
Compounds with the SCN3 core......Page 360
Compounds with the SCNSi2 core......Page 362
Compounds with the SCPMnRe core......Page 363
Compounds with the SCPSiLi core......Page 364
Compounds with the SCRu3 core......Page 365
Compounds with the SCFeCo2 core......Page 366
Compounds with the SeCN3 core......Page 367
References......Page 368
Biographical sketch......Page 371
6.12 Functions Containing at Least One Group 15 Element (and No Halogen or Chalcogen)......Page 373
By nucleophilic addition to guanidinium salts......Page 374
Miscellaneous syntheses......Page 375
Four phosphorus functions......Page 376
Three Similar Group 15 Elements......Page 377
Two nitrogen functions......Page 378
Two phosphorus and two silicon functions......Page 379
Two phosphorus and two gold functions......Page 380
Two phosphorus and two aluminum functions......Page 382
Two phosphorus and two nickel functions......Page 383
One phosphorus, two silicon, and one arsenic functions......Page 384
One nitrogen and three silicon functions......Page 385
One nitrogen and three ruthenium functions......Page 387
One nitrogen and three osmium functions......Page 388
By nucleophilic exchange of chlorine atoms on a silicon atom......Page 390
By reaction of carbon-phosphorus double bonds......Page 391
One phosphorus and three metal functions......Page 392
One phosphorus, one silicon, and two metal functions......Page 394
References......Page 395
Biographical sketch......Page 397
6.13 Functions Containing at Least One Metalloid (Si, Ge, or B) and No Halogen, Chalcogen, or Group 15 Element; Also Functions Containing Four Metals......Page 399
Formation by reaction between a trisilyllithiomethane and a halosilane......Page 400
Formation via addition reactions of silenes......Page 401
Thermolytic or photolytic methods......Page 403
Four B functions......Page 404
Three Si functions and one B function......Page 405
Two Si, one Ge, and one B functions......Page 406
Three Si and one group 1 metal functions......Page 407
Three Si and one group 2 metal functions......Page 411
Three Si and one group 13 metal functions......Page 412
Three Si and one group 14 metal functions......Page 415
Three Si and one transition metal functions......Page 416
Three Si and one lanthanide or actinide functions......Page 418
One Si, one Ge, one B, and one metal functions. Also two Ge, one Si, and one metal functions. Also two Ge, one B, and one metal functions. Also Two B, one Si, and one metal functions. Also two B, one Ge, and one metal functions......Page 419
Two B and two metal functions......Page 420
Methanes Bearing Three Similar and One Different Metal Functions......Page 421
References......Page 422
Biographical sketch......Page 426
6.14 Functions Containing a Carbonyl Group and at Least One Halogen......Page 427
Carbonic Difluoride......Page 428
Phosgene alternatives......Page 429
Carbonic Diiodide......Page 430
Carbonic bromide fluoride......Page 431
One Halogen and One Oxygen......Page 432
From phenols and phosgene......Page 433
From alcohols and phosgene......Page 434
Preparation of alpha-halogenated chloroformates by halogenation of chloroformates......Page 435
Other chloroformates......Page 436
Fluorothiolformate esters......Page 437
One Halogen and One Nitrogen......Page 438
Carbamoyl chlorides......Page 439
Chlorocarbonyl derivatives of phosphorus(III)......Page 440
One Halogen and One Metalloid (Boron, Silicon, or Germanium)......Page 441
References......Page 442
Biographical sketch......Page 445
6.15 Functions Containing a Carbonyl Group and at Least One Chalcogen (but No Halogen)......Page 447
Carbonates from phosgene and substitutes, chloroformates......Page 448
Carbonates from carbon oxides and carbonate salts......Page 450
Cyclic carbonates and transesterification......Page 451
Carbonates by iodolactonization......Page 452
1,3-Dithiol-2-ones by xanthogen disulfide-alkyne cycloaddition......Page 453
Thiocarbonates from activated carbonates......Page 454
Thiocarbonates from carbonothioic acid salts......Page 455
Oxygen and selenium functions......Page 456
Oxygen and tellurium functions......Page 457
Carbamates from chloroformates or phosgene equivalents......Page 458
Carbamates from N,N’-carbonyldiimidazole (CDI)......Page 459
Carbamates from carbonates or dicarbonates......Page 460
Carbamates from carbon oxides......Page 461
Phosphinecarboxylates by the Arbuzov reaction and related methods......Page 462
Thiocarbamates from carbamoyl chlorides and thiols......Page 463
Thiocarbamates from [3,3]-sigmatropic rearrangement......Page 464
Selenium and nitrogen functions......Page 465
References......Page 467
Biographical sketch......Page 470
6.16 Functions Containing a Carbonyl Group and Two Heteroatoms Other Than a Halogen or Chalcogen......Page 471
Starting materials......Page 472
Chemo-, regio-, and stereoselectivity of the addition......Page 473
Solution-phase reactions......Page 474
Dimerization and trimerization reactions......Page 475
Other cycloaddition reactions of isocyanates......Page 476
Carbonylation of amines......Page 478
Reactions of amines with phosgene......Page 479
Reactions of amines with chloroformates......Page 480
Reactions of amines with carbamates and thiocarbamates......Page 481
Preparation of acyclic ureas via disubstitution of symmetric ureas with amines......Page 482
Preparation of acyclic ureas......Page 483
Reactions of amines with amides and other carboxylic acid derivatives......Page 484
Oxidation......Page 485
Carbonyl derivatives with one nitrogen and one phosphorus(III) function......Page 486
Carbonyl derivatives with one nitrogen and one phosphorus(V) function......Page 487
Carbonyl derivatives with one nitrogen and one arsenic function (carbamoyl arsines)......Page 488
Carbonyl derivatives with one nitrogen and one boron function......Page 489
Carbonyl derivatives with one nitrogen function and one silicon function (carbamoyl silanes)......Page 490
Carbon monoxide insertion reactions......Page 491
Amination......Page 492
Reactions with heterocumulenes (isocyanates, ketenimines, azides, carbodiimides)......Page 493
Carbonyl Derivatives with Two P, As, Sb, or Bi Functions......Page 494
Carbonyl Derivatives with One Phosphorus and One Metal Function......Page 496
Carbonyl Derivatives with Two Silicon Functions......Page 497
Carbonyl Derivatives with One Metalloid and One Metal Function......Page 498
References......Page 499
Biographical sketch......Page 511
6.17 Functions Containing a Thiocarbonyl Group and at Least One Halogen; Also at Least One Chalcogen and No Halogen......Page 513
Thiocarbonyl Halides Containing Two Halogens......Page 514
Sulfoxides of Thiocarbonyl Halides (Sulfines)......Page 515
Chlorothioformates, ROC(Cl)=S......Page 516
Halogenodithioformates, RSC(Hal)=S......Page 517
From arenediazonium salts and CS2......Page 518
From thiophosgene and secondary amines or their synthetic equivalents......Page 519
Thionocarbonates (O,O-Diesters of Thiocarbonic Acid)......Page 520
From thiophosgene......Page 521
From chlorothionoformates......Page 522
From thiocarbonyldiimidazole......Page 527
Salts of O-alkyl esters of dithiocarbonic acid (xanthates) and bisalkoxythiocarbonyl disulfides......Page 528
From alkali salts of O-esters of dithiocarbonic acid......Page 529
From bisalkoxythiocarbonyl disulfides......Page 533
From carbon disulfide......Page 534
By radical addition to alkenes......Page 535
By other methods......Page 536
Sulfoxides of O,S-diesters of dithiocarbonic acid (sulfines)......Page 537
From O-alkyl or O-aryl chloroformates and amines......Page 538
From thiophosgene and 1,2-amino alcohols......Page 539
From CS2 and 1,2-amino alcohols......Page 540
From isothiocyanates and alcohols......Page 541
Other methods......Page 546
From carbon disulfide and base followed by alkylation......Page 548
From metal or ammonium dithiocarbamates......Page 549
From thiuram disulfides......Page 550
N-acyl-1,3-thiazolidine-2-thiones as auxiliary agents......Page 551
From thiophosgene or xanthates......Page 552
From the salts of trithiocarbonic acid or monoesters......Page 553
Other methods......Page 554
Synthesis and chemistry of 1,3-dithiol-2-thione-4,5-dithiolates and their zinc complexes......Page 555
References......Page 556
Biographical sketch......Page 562
From isothiocyanates......Page 563
From carbon disulfide......Page 571
From thiocarbonyl transfer reagents......Page 573
Miscellaneous methods......Page 574
From thiocyanate salts and alkyl thiocyanates......Page 575
From thiocarbamoyl transfer reagents......Page 577
From sulfur-transfer reagents......Page 579
From isothiocyanates......Page 582
From halothioamides......Page 584
Miscellaneous methods......Page 585
Thiocarbonyl Derivatives with Two Phosphorus Functions......Page 586
References......Page 587
Biographical sketch......Page 589
Overview......Page 591
Seleno- and Tellurocarbonyl Compounds Containing One Attached Halogen Atom......Page 592
Dithio-substituted Selenocarbonates (RS)2C=Se......Page 594
Diseleno-substituted Selenocarbonates (RSe)2C=Se......Page 596
Selenocarbonyl Functions Flanked by Two Different Chalcogen Atoms RX(C=Se)Y......Page 598
Selenocarbamates RO(C=Se)NHR, RS(C=Se)NHR, RSe(C=Se)NHR, RTe(C=Se)NHR......Page 599
Selenoureas (R2N)2C=Se......Page 602
Other Cyclic N(C=Se)N Compounds......Page 606
Telluroureas (R2N)2C=Te......Page 608
References......Page 609
Biographical sketch......Page 612
Introduction......Page 613
Carbonimidic difluorides, F2C=NR......Page 614
Carbonimidic dibromides, Br2C=NR......Page 615
Iminocarbonyl chlorides with one other heteroatom function......Page 616
Iminocarbonyl compounds with two sulfur functions......Page 617
Iminocarbonyl compounds with one oxygen and one sulfur function......Page 618
Iminocarbonyl compounds with one oxygen and one nitrogen function......Page 619
Iminocarbonyl compounds with one selenium and one other heteroatom function......Page 620
References......Page 621
Biographical sketch......Page 622
6.21 Functions Containing an Iminocarbonyl Group and Any Elements Other Than a Halogen or Chalcogen......Page 623
Iminocarbonyl Derivatives with Two Nitrogen Functions......Page 624
N-Unsubstituted iminocarbonyl derivatives from thioureas using mercury(II) salt as coupling reagent......Page 625
N-Unsubstituted iminocarbonyl derivatives from thioureas using carbodiimide as coupling reagent......Page 627
N-Unsubstituted iminocarbonyl derivatives from thioureas using Mukaiyama’s reagent......Page 628
N-Unsubstituted iminocarbonyl derivatives from isothioureas......Page 629
N-Unsubstituted iminocarbonyl derivatives from urethane-protected guanidines and triflyl-diurethane-protected guanidines......Page 631
N-Unsubstituted iminocarbonyl derivatives from di(azolyl)methanimines......Page 633
N-Unsubstituted iminocarbonyl derivatives by miscellaneous methods......Page 634
N-Alkyl iminocarbonyl derivatives......Page 635
N-Aryliminocarbonyl derivatives from guanidines......Page 638
N-Aryliminocarbonyl derivatives from thioureas......Page 639
N-Alkynyliminocarbonyl derivatives......Page 640
N-Acyliminocarbonyl derivatives......Page 641
Solid-phase methods......Page 642
N-Cyanoiminocarbonyl derivatives......Page 643
N-Haloiminocarbonyl derivatives......Page 644
Sulfur derivatives......Page 645
Imino, nitro, nitroso, and azido derivatives......Page 648
Phosphorus(III) derivatives......Page 650
Phosphorus(V) derivatives......Page 651
As, Sb, and Bi derivatives......Page 655
N-Si, N-Ge, and N-B iminocarbonyl derivatives......Page 656
N-Alkylimino derivatives with one P or As function......Page 657
N-Acylimino derivatives with one P function......Page 658
Diazonium derivatives with one P function......Page 659
N,N-Dialkyliminium derivatives with one P function......Page 660
Silicon derivatives......Page 662
Transition metal derivatives......Page 663
Bis(phosphino)iminocarbonyl derivatives......Page 665
Bis(phosphinyl)iminocarbonyl derivatives......Page 667
Silicon derivatives......Page 668
Iminocarbonyl derivatives with one As, Sb, or Bi function and one Si, Ge, or B function......Page 669
Transition metals......Page 670
N-Alkyl- and N-aryliminocarbonyl derivatives......Page 671
N-Silyliminocarbonyl derivatives......Page 672
Iminocarbonyl Derivatives Containing Two Metal Functions......Page 673
References......Page 675
Biographical sketch......Page 678
6.22 Functions Containing Doubly Bonded P, As, Sb, Bi, Si, Ge, B, or a Metal......Page 679
Dihalomethylenephosphines, Hal2C=PY......Page 680
Oxygen- and sulfur-substituted methylenephosphines, RO(X)C=PY and RS(X)C=PY......Page 682
Synthesis by condensation reactions......Page 683
Synthesis via free carbenes......Page 684
Miscellaneous......Page 685
From C,C-dihalomethylenephosphines......Page 686
By elimination reactions......Page 687
By derivatization of P-halo-C,C-bis(TMS)methylenephosphines......Page 688
Phosphaalkenyl metal species......Page 689
Bridging aryl isocyaphide ligands......Page 690
C,C-diheterosubstituted methylenearsines, X2C=AsY......Page 691
Stabilized [X2C=PY2]+ species......Page 693
Functions with a phosphorus-metal sigma-donor bond, X2C=P(MLn)Y......Page 694
From organodichlorophosphines......Page 695
From methylenephosphines and iminophosphines......Page 696
Derivatization via phosphoranylidene carbenoids......Page 697
Dihalosubstituted ylides, Hal2C=PY3......Page 698
Nitrogen-, phosphorus-, arsenic-, and antimony-substituted ylides, R2E(X)C=PY3 (E=N, P, As, or Sb)......Page 699
Silicon-, germanium-, and boron-substituted ylides, R3E(X)C=PY3 (E=Si or Ge) and R2B(X)C=PY3......Page 703
Metal-substituted ylides, LnM(X)C=PY3......Page 704
Stibonium and bismuthonium ylides bearing heterosubstituents, X2C=EY3 (E=Sb or Bi)......Page 705
Diheterosubstituted silaethenes, X2C=SiY2......Page 706
C,C-Diheterosubstituted germaethenes, X2C=GeY2......Page 709
Functions Incorporating a Doubly Bonded Boron......Page 711
Methyleneboranes, X2C=B-Y......Page 712
Functions Incorporating A Doubly Bonded Metal......Page 713
N-Heterocyclic carbene complexes......Page 714
Silicon-substituted carbene complexes, R3Si(X)C=MLn......Page 720
Functions with a Formal Tin-Carbon and Lead-Carbon Double Bond......Page 722
References......Page 724
Biographical sketch......Page 729
6.23 Tricoordinated Stabilized Cations, Anions, and Radicals, +CX1X2X3, -CX1X2X3, and .CX1X2X3......Page 731
Cations bearing one halogen, one chalcogen, and one nitrogen functions......Page 732
Cations bearing one halogen and two nitrogen functions......Page 733
Three sulfur functions......Page 734
Two sulfur and one nitrogen functions......Page 735
One oxygen and two nitrogen functions......Page 736
Cations Bearing Chalcogen, Metal, and (Possibly) Nitrogen Functions......Page 737
Cations Bearing Three Nitrogen Functions......Page 738
Cations Bearing Nitrogen and Other Element Functions......Page 739
Carbon-Centered Carbanions Bearing Three Heteroatom Functions......Page 740
Carbanions Bearing Three Phosphorus Functions......Page 741
Carbon-Centered Radicals Bearing Three Heteroatom Functions......Page 742
References......Page 743
Biographical sketch......Page 745