Handbook of Reagents for Organic Synthesis
Reagents for Silicon-Mediated Organic Synthesis
Will be published approx. on 14. October 2011
Book
Hardback
854 pages
978-0-470-71023-4 (ISBN)
Description
Over the last three decades the importance of organosilicon chemistry has greatly increased because it has opened a number of new synthetic strategies. Silicon reagents are usually low-cost, versatile and allow a wide range of reactions. This is the first Handbook to compile essential Silicon containing reagents and makes use of the leading reagent database e-EROS. Another hot volume in the series Handbooks of Reagents for Organic Synthesis, this is a must-have resource for all synthetic chemists working in drug development and medicinal chemistry.
For the selection the Editor focussed on three key synthetic approaches with the greatest impact:
1. Use of silicon as a 'temporary tether' by unifying a reactive pair of functional groups and taking advantage of their template-biased intramolecular cyclization.
2. The specific use of the silane functionality as a hetero t-butyl group, often colloquially referred to as the use of silicon as a 'fat proton'.
3. The use of the Brook rearrangement as an 'anion relay stratagem'.
A new feature in this Handbook is the reagent finder, an alphabetically organized lookup table arranged by organic functionality and specific structure of the silicon atom to which it is bound.
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Philip L. Fuchs
Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis
E-Book
05/2013
Wiley
€107.99
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Persons
Philip Fuchs began his career at Purdue in 1973. Since that time, he has graduated an extended family of 55 Ph.D.s. His awards and honors include an Eli Lilly young faculty fellowship (1975), an Alfred P. Sloan fellowship (1977), a Pioneer in Laboratory Robotics award (1986), a Martin teaching award (1991), and being voted by the students as one of Top 10 Teachers in School of Science at Purdue (1991, 1993, 1995, 1996).
Fuchs has consulted for Pfizer, and Eli Lilly, served on the editorial board of The Journal of Organic Chemistry, and is currently an executive editor for the Electronic Encyclopedia of Organic Reagents (e-EROS), an online dynamic encyclopedia published by John Wiley & Sons.
Fuchs has consulted for Pfizer, and Eli Lilly, served on the editorial board of The Journal of Organic Chemistry, and is currently an executive editor for the Electronic Encyclopedia of Organic Reagents (e-EROS), an online dynamic encyclopedia published by John Wiley & Sons.
Content
Preface xiii
Introduction xv
Reagent Finder Table xxiii
Short Note on InChIs and InChIKeys xxxi
3-Acetoxy-2-trimethylsilylmethyl-1-propene 1
Allyl(2-chloroethyl)dimethylsilane 9
Allyl Trichlorosilane 10
Allyltrimethylsilane 14
Allyltrimethylsilylzinc Chloride 24
Ammonium Hexafluorosilicate 25
Azidotrimethylsilane 26
Benzene, [[Difluoro(trimethylsilyl)methyl]seleno] 33
Benzene, [[Difluoro(trimethylsilyl)methyl]thio]- 36
Benzene, [[(1E)-2-(Trimethylsilyl)ethenyl]seleno] 39
Benzene, [[(1E)-2-trimethylsilyl)ethenyl]sulfonyl]- 42
2,1-Benzoxasilole, 1,3-Dihydro-1,1-dimethyl- 43
N-Benzyl-N-(methoxymethyl)-Ntrimethylsilylmethylamine 44
1,2-Bis(t-butyldimethylsilyl)hydrazine 46
1,2-Bis(chlorodimethylsilyl)ethane 48
1,4-Bis(dimethylamino)-1,1,4,4-tetramethyldisilethylene 50
Bis(1-methoxy-2-methyl-1-propenyloxy)dimethylsilane 51
Bis(methylthio)(trimethylsilyl)methane 52
[Bis(2-pyridyldimethylsilyl)methyl]lithium 54
1,3-Bis(triisopropylsilyl)propyne 56
N,O-Bis(trimethylsilyl)acetamide 58
(1E,3E)-1,4-Bis(trimethylsilyl)-1,3-butadiene 73
Bis(ß-trimethylsilylethanesulfonyl)imide 74
N,O-Bis(trimethylsilyl)hydroxylamine 75
Bis[(trimethylsilyl)methyl]zinc 76
Bis(trimethylsilyl) Peroxide 79
Bis(trimethylsilyl) Selenide 82
Bis(trimethylsilyl) Sulfide 83
Bromomagnesium Hexamethyldisilazide 85
(Bromomethyl)chlorodimethylsilane 85
Bromotrimethylsilane 92
(E)-1-Bromo-4-trimethylsilyl-1-buten-3-yne 100
(Z)-2-Bromo-1-(trimethylsilyloxy)ethylene 105
2-Bromo-3-trimethylsilyl-1-propene 106
(1-Bromovinyl)trimethylsilane 109
t-Butyldimethylchlorosilane 110
t-Butyldimethylsilyl Cyanide 120
(t-Butyldimethylsilyl)diphenylphosphine 121
2-t-Butyldimethylsilyl-1,3-dithiane 122
O-(t-Butyldimethylsilyl)hydroxylamine 124
N-(t-Butyldimethylsilyl)-N-methyltrifluoroacetamide 125
t-Butyldimethylsilyl Trifluoromethanesulfonate 127
t-Butyldiphenylchlorosilane 135
1-t-Butylthio-1-t-butyldimethyl-silyloxyethylene 138
1-t-Butylthio-1-t-butyldimethylsilyloxypropene 141
t-Butyl Trimethylsilylacetate 147
3-Butyn-2-ol, 4-(Trimethylsilyl)- 148
Chlorodiisopropylsilane 151
Chlorodimethylsilane 156
Chlorodimethylvinylsilane 157
Chlorodiphenylsilane 162
(Chloromethyl)dimethylphenylsilane 162
(E)-(3-Chloro-1-methyl-1-propenyl)-trimethylsilane 166
1-Chloro-1-methylsiletane 166
Chlorotrimethylsilane 170
Chlorotriphenylsilane 182
Cyanotrimethylsilane 184
Diazo(trimethylsilyl)methyllithium 191
(Dibromomethyl)trimethylsilane 197
Di-t-butylchlorosilane 198
Di-t-butyldichlorosilane 201
trans-1,1-Di-t-butyl-2,3-dimethylsilirane 207
Di-t-butylsilyl Bis(trifluoromethanesulfonate) 209
Dichlorodiisopropylsilane 222
Dichlorodimethylsilane 228
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 230
1,1-Dichloro-2,2,2-trimethyl-1-phenyldisilane 233
Dicyanodimethylsilane 234
1,2-Diethoxy-1,2-bis(trimethylsilyloxy)ethylene 235
N,N-Diethylaminodimethylsilane 237
Diethyl[dimethyl(phenyl)silyl]aluminum 237
Diiododimethylsilane 238
Diisopropyl Chlorosilane, Polymer-supported 240
Diisopropylsilyl Bis(trifluoromethanesulfonate) 241
Dilithium Cyanobis(dimethylphenylsilyl)-cuprate 248
(a,a-Dimethylallyl)trimethylsilane 252
(2-Dimethylaminomethylphenyl)phenylsilane 253
Dimethyl(phenyl)silane 254
Dimethylphenylsilyllithium 255
1,1-Dimethylsilacyclobutane 261
Dimethylthexylsilyl Chloride 263
Dimethylthexylsilyl Trifluoromethanesulfonate 265
1,3,2-Dioxaborolane, 2-(Dimethylphenylsilyl)-4,4,5,5- tetramethyl-, 1,3,2-Dioxaborolane, 4,4,5,5-Tetramethyl- 2-(methyldiphenylsilyl)-, 1,3,2-Dioxaborolane, 4,4,5,5- Tetramethyl-2-(triphenylsilyl)- 270
Diphenyldifluorosilane 276
Disilane, 1,1,1,2,2,2-hexamethyl- 278
1-Ethoxy-1-(trimethylsilyloxy)cyclopropane 285
Ethoxy(trimethylsilyl)acetylene 289
Ethyl Lithio(trimethylsilyl)acetate 293
Ethyl (Methyldiphenylsilyl)acetate 295
Ethyl 2-(Methyldiphenylsilyl)propanoate 296
Ethyl Trimethylsilylacetate 297
Fluorosilicic Acid 301
Formamide, N-N,bis(trimethylsilyl)- 302
Hexachlorodisilane 309
Hexamethylcyclotrisiloxane 310
Hexamethyldisiloxane 313
Hexamethyldisilazane 317
(Iodoethynyl)trimethylsilane 321
(Iodomethyl)trimethylsilane 323
Iodotrimethylsilane 325
(E)-1-Iodo-3-trimethylsilyl-2-butene 336
3-Iodo-2-trimethylsilylmethyl-1-propene 338
Isocyanatotrimethylsilane 339
Ketene t-Butyldimethylsilyl Methyl Acetal 341
3-Lithio-1-triisopropylsilyl-1-propyne 347
Lithium N-Benzyltrimethylsilylamide 349
Lithium Bis[dimethyl(phenyl)silyl]cuprate 350
Lithium Cyano(dimethylphenylsilyl)cuprate 353
Lithium Hexamethyldisilazide 356
Methanamine, 1,1-Bis(trimethylsilyl) 369
Methanesulfonamide, 1,1,1-Trifluoro-N[(trifluoromethyl)sulfonyl]-N(trimethylsilyl)- 372
(Methoxymethyl)bis(trimethylsilyl)amine 374
1-Methoxy-2-methyl-1-(trimethylsilyloxy)propene 376
N-Methyl-N,O-bis(trimethylsilyl)-hydroxylamine 380
Methyldiphenylchlorosilane 381
(Methylthio)trimethylsilane 388
Methyltrichlorosilane 389
Methyl Trichlorosilyl Ketene Acetal (1) 393
Methyl 2-Trimethylsilylacrylate 396
1-Methyl-1-(trimethylsilyl)allene 397
2-Methyl-2-(trimethylsilyloxy)-3-pentanone 400
PDMS Thimbles 403
Phenylsilane-Cesium Fluoride 408
(2-Phenylsulfonylethyl)trimethylsilane 409
Phenylthiobis(trimethylsilyl)methane 411
(Phenylthiomethyl)trimethylsilane 412
(Phenylthio)trimethylsilane 414
1-(Phenylthio)-1-(trimethylsilyl)cyclopropane 418
1-Phenylthio-1-trimethylsilylethylene 419
2-(Phenylthio)-2-(trimethylsilyl)propane 420
Phenyl Trimethylsilyl Selenide 421
Phosphine, Tris(trimethylsilyl)- 422
Polymethylhydrosiloxane 427
Potassium Hexamethyldisilazide 432
(+)-9-(1S,2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)- 9-borabicyclo[3.3.2]decane 453
2-Pyridyldimethylsilane 457
Silane, 1,1-(Chloromethylene)bis[1,1,1]-trimethyl- 461
Silane, Chlorotri-2-propen-1-yl- 463
Silane, 1,1-(1-Propene-1,3-diyl)bis[1,1,1-trimethyl-(E)
Silane, 1,1-(1-Propene-1,3-diyl)bis[1,1,1-trimethyl-(Z)
Silane, 1,1-(1-Propene-1,3-diyl)bis[1,1,1- trimethyl-(E + Z) 464
Sodium Hexamethyldisilazide 468
Tetrabutylammonium Difluorotriphenylsilicate 479
2,4,6,8-Tetraethenyl-2,4,6,8-tetramethylcyclotetrasiloxane 484
3-Tetrahydropyranyloxy-1-trimethylsilyl-1-propyne 487
1,1,3,3-Tetramethyldisilazane 488
1,1,2,2-Tetraphenyldisilane 490
Trialkylsilyl Cyanide, Polymer-supported 494
Tribenzylchlorosilane 496
Tri(t-butoxy)silanethiol 497
(E)-1-Tri-n-butylstannyl-2-trimethylsilylethylene 499
Trichloroiodosilane 500
Triethoxysilane 501
Triethylsilane 506
Triethylsilyl Hydrotrioxide 514
3-Triethylsilyloxy-1,4-pentadiene 515
(a-Triethylsilyl)propionaldehyde Cyclohexylimine 516
Triethylsilyl Trifluoromethanesulfonate 517
Trimethylsilyl Trifluoromethanesulfonate 518
Trifluoromethanesulfonic Acid, Chlorobis (1,1-Dimethylethyl)silyl Ester 537
Trifluoromethyltrimethylsilane 539
Triisopropylsilanethiol 546
(Triisopropylsilyl)acetylene 550
Triisopropylsilyl Chloride 554
Triisopropylsilylethynyl Triflone 558
Triisopropylsilyl Trifluoromethanesulfonate 559
Trimethylsilylacetic Acid 562
Trimethylsilylacetone 563
Trimethylsilylacetonitrile 564
Trimethylsilylacetylene 569
(Trimethylsilyl)allene 580
Trimethylsilylallyllithium 582
(E)-1-Trimethylsilyl-1,3-butadiene 585
3-Trimethylsilyl-3-buten-2-one 586
9-[1-(Trimethylsilyl)-2(E)-butenyl] -9-borabicyclo[3.3.1]nonane 588
Trimethylsilylcopper 589
Trimethylsilyldiazomethane 590
Trimethylsilyldiethylamine 598
2-Trimethylsilyl-1,3-dithiane 604
2-(Trimethylsilyl)ethanesulfonamide 609
ß-Trimethylsilylethanesulfonyl Chloride 611
[N-(2-(Trimethylsilyl)ethanesulfonyl)-imino]phenyliodane 617
2-(Trimethylsilyl)ethanethiol 618
2-(Trimethylsilyl)ethanol 622
2-(Trimethylsilyl)ethoxycarbonylimidazole 627
2-(Trimethylsilyl)ethoxymethyl Chloride 628
[2-(Trimethylsilyl)ethoxymethyl]triphenylphosphonium Chloride 633
2-(Trimethylsilyl)ethyl Chloroformate 634
2-(Trimethylsilyl)ethyl 3-Nitro-1H-1,2,4-triazole-1-carboxylate 636
(Trimethylsilyl)ethynylcopper(I) 637
Trimethylsilyl Fluorosulfonyldifluoroacetate 638
N-(Trimethylsilyl)imidazole 640
Trimethylsilylketene 645
Trimethylsilyllithium 650
Trimethylsilyl Methanenitronate 653
1-Trimethylsilyl-1-methoxyallene 656
Trimethylsilylmethyl Azide 657
1-[(Trimethylsilyl)methyl]-1H-benzotriazole 658
2-Trimethylsilylmethyl-1,3-butadiene 660
3-[(Trimethylsilyl)methyl]-3-butenoic Acid Methyl Ester 662
Trimethylsilylmethyllithium 664
Trimethylsilylmethylmagnesium Chloride 666
Trimethylsilylmethylpotassium 674
2-Trimethylsilylmethyl-2-propen-1-ol 675
1-Trimethylsilyloxy-1,3-butadiene 677
2-Trimethylsilyloxy-1,3-butadiene 681
2-Trimethylsilyloxyfuran 684
(Z)-2-(Trimethylsilyloxy)vinyllithium 693
5-Trimethylsilyl-1,3-pentadiene 695
2-(Trimethylsilyl)phenyl Triflate 697
Trimethylsilylpotassium 700
2-Trimethylsilyl-1,3-propanediol 701
3-Trimethylsilyl-2-propen-1-yl Acetate 703
3-Trimethylsilyl-1-propyne 704
3-Trimethylsilyl-2-propynylcopper(I) 711
2-(Trimethylsilyl)thiazole 712
Trimethylsilyltributylstannane 719
3-Trimethylsilyl-3-trimethylsilyloxy-1-propene 723
(E)-1-Trimethylsilyl-2-trimethylstannylethylene 724
(Trimethylsilyl)vinylketene 725
1-(Trimethylsilyl)vinyllithium 726
(E)-2-(Trimethylsilyl)vinyllithium 729
1-(Trimethylsilyl)vinylmagnesium Bromide-Copper(I) Iodide 730
Trimethyl{2-[(tributylstannyl)methyl]-2-propenyl}silane 731
Triphenylsilane 733
Tris(dimethylamino)sulfonium Difluorotrimethylsilicate 739
Tris(trimethylsilyl)aluminum 745
Tris(trimethylsilyl)methane 746
Tris(trimethylsilyl)silane 747
Vinyltrimethylsilane 755
List of Contributors 763
Reagent Formula Index 779
Subject Index 785 ???