Reagents for Silicon-Mediated Organic Synthesis (eBook, PDF)

Redaktion: Fuchs, Philip L.

• Format: PDF

Produktbeschreibung

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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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 816
• Erscheinungstermin: 30. Mai 2013
• Englisch
• ISBN-13: 9781118636138
• Artikelnr.: 38599192

Autorenporträt

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.

Inhaltsangabe

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 ???