Reagents for Silicon-Mediated Organic Synthesis
by Fuchs, Philip L.Buy New
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Summary
Author Biography
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.
Table of Contents
| Preface | p. xiii |
| Introduction | p. xv |
| Reagent Finder Table | p. xxiii |
| Short Note on InChIs and InChIKeys | p. xxxi |
| 3-Acetoxy-2-trimethylsilylmethyl-1-propene | p. 1 |
| Allyl(2-chloroethyl)dimethylsilane | p. 9 |
| Allyl Trichlorosilane | p. 10 |
| Allyltrimethylsilane | p. 14 |
| Allyltrimethylsilylzinc Chloride | p. 24 |
| Ammonium Hexafluorosilicate | p. 25 |
| Azidotrimethylsilane | p. 26 |
| Benzene, [[Difluoro(trimethylsilyl)methyl]seleno] | p. 33 |
| Benzene, [[Difluoro(trimethylsilyl)methyl]thio]- | p. 36 |
| Benzene, [[(1E)-2-(Trimethylsilyl)ethenyl]seleno] | p. 39 |
| Benzene, [[(1E)-2-trimethylsilyl)ethenyl]sulfonyl]- | p. 42 |
| 2,1-Benzoxasilole, 1,3-Dihydro-1,1-dimethyl- | p. 43 |
| N-Benzyl-N-(methoxymethyl)-Ntrimethylsilylmethylamine | p. 44 |
| 1,2-Bis(t-butyldimethylsilyl)hydrazine | p. 46 |
| 1,2-Bis(chlorodimethylsilyl)ethane | p. 48 |
| 1,4-Bis(dimethylamino)-1,1,4,4-tetramethyldisilethylene | p. 50 |
| Bis(1-methoxy-2-methyl-1-propenyloxy)dimethylsilane | p. 51 |
| Bis(methylthio)(trimethylsilyl)methane | p. 52 |
| [Bis(2-pyridyldimethylsilyl)methyl]lithium | p. 54 |
| 1,3-Bis(triisopropylsilyl)propyne | p. 56 |
| N,O-Bis(trimethylsilyl)acetamide | p. 58 |
| (1E,3E)-1,4-Bis(trimethylsilyl)-1,3-butadiene | p. 73 |
| Bis(ß-trimethylsilylethanesulfonyl)imide | p. 74 |
| N,O-Bis(trimethylsilyl)hydroxylamine | p. 75 |
| Bis[(trimethylsilyl)methyl]zinc | p. 76 |
| Bis(trimethylsilyl) Peroxide | p. 79 |
| Bis(trimethylsilyl) Selenide | p. 82 |
| Bis(trimethylsilyl) Sulfide | p. 83 |
| Bromomagnesium Hexamethyldisilazide | p. 85 |
| (Bromomethyl)chlorodimethylsilane | p. 85 |
| Bromotrimethylsilane 92, E)-1-Bromo-4-trimethylsilyl-1-buten-3-yne 100, Z)-2-Bromo-1-(trimethylsilyloxy)ethylene | p. 105 |
| 2-Bromo-3-trimethylsilyl-1-propene | p. 106 |
| (1-Bromovinyl)trimethylsilane | p. 109 |
| t-Butyldimethylchlorosilane | p. 110 |
| t-Butyldimethylsilyl Cyanide 120 t-Butyldimethylsilyl)diphenylphosphine | p. 121 |
| 2-t-Butyldimethylsilyl-1,3-dithiane | p. 122 |
| O-(t-Butyldimethylsilyl)hydroxylamine | p. 124 |
| N-(t-Butyldimethylsilyl)-N-methyltrifluoroacetamide | p. 125 |
| t-Butyldimethylsilyl Trifluoromethanesulfonate | p. 127 |
| t-Butyldiphenylchlorosilane | p. 135 |
| 1-t-Butylthio-1-t-butyldimethyl-silyloxyethylene | p. 138 |
| 1-t-Butylthio-1-t-butyldimethylsilyloxypropene | p. 141 |
| t-Butyl Trimethylsilylacetate | p. 147 |
| 3-Butyn-2-ol, 4-(Trimethylsilyl)- | p. 148 |
| Chlorodiisopropylsilane | p. 151 |
| Chlorodimethylsilane | p. 156 |
| Chlorodimethylvinylsilane | p. 157 |
| Chlorodiphenylsilane | p. 162 |
| (Chloromethyl)dimethylphenylsilane 162 E)-(3-Chloro-1-methyl-1-propenyl)-trimethylsilane | p. 166 |
| 1-Chloro-1-methylsiletane | p. 166 |
| Chlorotrimethylsilane | p. 170 |
| Chlorotriphenylsilane | p. 182 |
| Cyanotrimethylsilane | p. 184 |
| Diazo(trimethylsilyl)methyllithium | p. 191 |
| (Dibromomethyl)trimethylsilane | p. 197 |
| Di-t-butylchlorosilane | p. 198 |
| Di-t-butyldichlorosilane | p. 201 |
| trans-1,1-Di-t-butyl-2,3-dimethylsilirane | p. 207 |
| Di-t-butylsilyl Bis(trifluoromethanesulfonate) | p. 209 |
| Dichlorodiisopropylsilane | p. 222 |
| Dichlorodimethylsilane | p. 228 |
| 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane | p. 230 |
| 1,1-Dichloro-2,2,2-trimethyl-1-phenyldisilane | p. 233 |
| Dicyanodimethylsilane | p. 234 |
| 1,2-Diethoxy-1,2-bis(trimethylsilyloxy)ethylene | p. 235 |
| N,N-Diethylaminodimethylsilane | p. 237 |
| Diethyl[dimethyl(phenyl)silyl]aluminum | p. 237 |
| Diiododimethylsilane | p. 238 |
| Diisopropyl Chlorosilane, Polymer-supported | p. 240 |
| Diisopropylsilyl Bis(trifluoromethanesulfonate) | p. 241 |
| Dilithium Cyanobis(dimethylphenylsilyl)-cuprate 248 a,a-Dimethylallyl)trimethylsilane | p. 252 |
| (2-Dimethylaminomethylphenyl)phenylsilane | p. 253 |
| Dimethyl(phenyl)silane | p. 254 |
| Dimethylphenylsilyllithium | p. 255 |
| 1,1-Dimethylsilacyclobutane | p. 261 |
| Dimethylthexylsilyl Chloride | p. 263 |
| Dimethylthexylsilyl Trifluoromethanesulfonate | p. 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)- | p. 270 |
| Diphenyldifluorosilane | p. 276 |
| Disilane, 1,1,1,2,2,2-hexamethyl- | p. 278 |
| 1-Ethoxy-1-(trimethylsilyloxy)cyclopropane | p. 285 |
| Ethoxy(trimethylsilyl)acetylene | p. 289 |
| Ethyl Lithio(trimethylsilyl)acetate | p. 293 |
| Ethyl (Methyldiphenylsilyl)acetate | p. 295 |
| Ethyl 2-(Methyldiphenylsilyl)propanoate | p. 296 |
| Ethyl Trimethylsilylacetate | p. 297 |
| Fluorosilicic Acid | p. 301 |
| Formamide, N-N,bis(trimethylsilyl)- | p. 302 |
| Hexachlorodisilane | p. 309 |
| Hexamethylcyclotrisiloxane | p. 310 |
| Hexamethyldisiloxane | p. 313 |
| Hexamethyldisilazane | p. 317 |
| (Iodoethynyl)trimethylsilane | p. 321 |
| (Iodomethyl)trimethylsilane | p. 323 |
| Iodotrimethylsilane 325 E)-1-Iodo-3-trimethylsilyl-2-butene | p. 336 |
| 3-Iodo-2-trimethylsilylmethyl-1-propene | p. 338 |
| Isocyanatotrimethylsilane | p. 339 |
| Ketene t-Butyldimethylsilyl Methyl Acetal | p. 341 |
| 3-Lithio-1-triisopropylsilyl-1-propyne | p. 347 |
| Lithium N-Benzyltrimethylsilylamide | p. 349 |
| Lithium Bis[dimethyl(phenyl)silyl]cuprate | p. 350 |
| Lithium Cyano(dimethylphenylsilyl)cuprate | p. 353 |
| Lithium Hexamethyldisilazide | p. 356 |
| Methanamine, 1,1-Bis(trimethylsilyl) | p. 369 |
| Methanesulfonamide, 1,1,1-Trifluoro-N[(trifluoromethyl)sulfonyl]-N(trimethylsilyl)- | p. 372 |
| (Methoxymethyl)bis(trimethylsilyl)amine | p. 374 |
| 1-Methoxy-2-methyl-1-(trimethylsilyloxy)propene | p. 376 |
| N-Methyl-N,O-bis(trimethylsilyl)-hydroxylamine | p. 380 |
| Methyldiphenylchlorosilane | p. 381 |
| (Methylthio)trimethylsilane | p. 388 |
| Methyltrichlorosilane | p. 389 |
| Methyl Trichlorosilyl Ketene Acetal (1) | p. 393 |
| Methyl 2-Trimethylsilylacrylate | p. 396 |
| 1-Methyl-1-(trimethylsilyl)allene | p. 397 |
| 2-Methyl-2-(trimethylsilyloxy)-3-pentanone | p. 400 |
| PDMS Thimbles | p. 403 |
| Phenylsilane-Cesium Fluoride | p. 408 |
| (2-Phenylsulfonylethyl)trimethylsilane | p. 409 |
| Phenylthiobis(trimethylsilyl)methane | p. 411 |
| (Phenylthiomethyl)trimethylsilane | p. 412 |
| (Phenylthio)trimethylsilane | p. 414 |
| 1-(Phenylthio)-1-(trimethylsilyl)cyclopropane | p. 418 |
| 1-Phenylthio-1-trimethylsilylethylene | p. 419 |
| 2-(Phenylthio)-2-(trimethylsilyl)propane | p. 420 |
| Phenyl Trimethylsilyl Selenide | p. 421 |
| Phosphine, Tris(trimethylsilyl)- | p. 422 |
| Polymethylhydrosiloxane | p. 427 |
| Potassium Hexamethyldisilazide | p. 432 |
| (+)-9-(1S,2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)- 9-borabicyclo[3.3.2]decane | p. 453 |
| 2-Pyridyldimethylsilane | p. 457 |
| Silane, 1,1-(Chloromethylene)bis[1,1,1]-trimethyl- | p. 461 |
| Silane, Chlorotri-2-propen-1-yl- | p. 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) | p. 464 |
| Sodium Hexamethyldisilazide | p. 468 |
| Tetrabutylammonium Difluorotriphenylsilicate | p. 479 |
| 2,4,6,8-Tetraethenyl-2,4,6,8-tetramethylcyclotetrasiloxane | p. 484 |
| 3-Tetrahydropyranyloxy-1-trimethylsilyl-1-propyne | p. 487 |
| 1,1,3,3-Tetramethyldisilazane | p. 488 |
| 1,1,2,2-Tetraphenyldisilane | p. 490 |
| Trialkylsilyl Cyanide, Polymer-supported | p. 494 |
| Tribenzylchlorosilane | p. 496 |
| Tri(t-butoxy)silanethiol 497 E)-1-Tri-n-butylstannyl-2-trimethylsilylethylene | p. 499 |
| Trichloroiodosilane | p. 500 |
| Triethoxysilane | p. 501 |
| Triethylsilane | p. 506 |
| Triethylsilyl Hydrotrioxide | p. 514 |
| 3-Triethylsilyloxy-1,4-pentadiene 515 a-Triethylsilyl)propionaldehyde Cyclohexylimine | p. 516 |
| Triethylsilyl Trifluoromethanesulfonate | p. 517 |
| Trimethylsilyl Trifluoromethanesulfonate | p. 518 |
| Trifluoromethanesulfonic Acid, Chlorobis (1,1-Dimethylethyl)silyl Ester | p. 537 |
| Trifluoromethyltrimethylsilane | p. 539 |
| Triisopropylsilanethiol | p. 546 |
| (Triisopropylsilyl)acetylene | p. 550 |
| Triisopropylsilyl Chloride | p. 554 |
| Triisopropylsilylethynyl Triflone | p. 558 |
| Triisopropylsilyl Trifluoromethanesulfonate | p. 559 |
| Trimethylsilylacetic Acid | p. 562 |
| Trimethylsilylacetone | p. 563 |
| Trimethylsilylacetonitrile | p. 564 |
| Trimethylsilylacetylene | p. 569 |
| (Trimethylsilyl)allene | p. 580 |
| Trimethylsilylallyllithium 582 E)-1-Trimethylsilyl-1,3-butadiene | p. 585 |
| 3-Trimethylsilyl-3-buten-2-one | p. 586 |
| 9-[1-(Trimethylsilyl)-2(E)-butenyl] -9-borabicyclo[3.3.1]nonane | p. 588 |
| Trimethylsilylcopper | p. 589 |
| Trimethylsilyldiazomethane | p. 590 |
| Trimethylsilyldiethylamine | p. 598 |
| 2-Trimethylsilyl-1,3-dithiane | p. 604 |
| 2-(Trimethylsilyl)ethanesulfonamide | p. 609 |
| ß-Trimethylsilylethanesulfonyl Chloride | p. 611 |
| [N-(2-(Trimethylsilyl)ethanesulfonyl)-imino]phenyliodane | p. 617 |
| 2-(Trimethylsilyl)ethanethiol | p. 618 |
| 2-(Trimethylsilyl)ethanol | p. 622 |
| 2-(Trimethylsilyl)ethoxycarbonylimidazole | p. 627 |
| 2-(Trimethylsilyl)ethoxymethyl Chloride | p. 628 |
| [2-(Trimethylsilyl)ethoxymethyl]triphenylphosphonium Chloride | p. 633 |
| 2-(Trimethylsilyl)ethyl Chloroformate | p. 634 |
| 2-(Trimethylsilyl)ethyl 3-Nitro-1H-1,2,4-triazole-1-carboxylate | p. 636 |
| (Trimethylsilyl)ethynylcopper(I) | p. 637 |
| Trimethylsilyl Fluorosulfonyldifluoroacetate | p. 638 |
| N-(Trimethylsilyl)imidazole | p. 640 |
| Trimethylsilylketene | p. 645 |
| Trimethylsilyllithium | p. 650 |
| Trimethylsilyl Methanenitronate | p. 653 |
| 1-Trimethylsilyl-1-methoxyallene | p. 656 |
| Trimethylsilylmethyl Azide | p. 657 |
| 1-[(Trimethylsilyl)methyl]-1H-benzotriazole | p. 658 |
| 2-Trimethylsilylmethyl-1,3-butadiene | p. 660 |
| 3-[(Trimethylsilyl)methyl]-3-butenoic Acid Methyl Ester | p. 662 |
| Trimethylsilylmethyllithium | p. 664 |
| Trimethylsilylmethylmagnesium Chloride | p. 666 |
| Trimethylsilylmethylpotassium | p. 674 |
| 2-Trimethylsilylmethyl-2-propen-1-ol | p. 675 |
| 1-Trimethylsilyloxy-1,3-butadiene | p. 677 |
| 2-Trimethylsilyloxy-1,3-butadiene | p. 681 |
| 2-Trimethylsilyloxyfuran 684 Z)-2-(Trimethylsilyloxy)vinyllithium | p. 693 |
| 5-Trimethylsilyl-1,3-pentadiene | p. 695 |
| 2-(Trimethylsilyl)phenyl Triflate | p. 697 |
| Trimethylsilylpotassium | p. 700 |
| 2-Trimethylsilyl-1,3-propanediol | p. 701 |
| 3-Trimethylsilyl-2-propen-1-yl Acetate | p. 703 |
| 3-Trimethylsilyl-1-propyne | p. 704 |
| 3-Trimethylsilyl-2-propynylcopper(I) | p. 711 |
| 2-(Trimethylsilyl)thiazole | p. 712 |
| Trimethylsilyltributylstannane | p. 719 |
| 3-Trimethylsilyl-3-trimethylsilyloxy-1-propene 723 E)-1-Trimethylsilyl-2-trimethylstannylethylene | p. 724 |
| (Trimethylsilyl)vinylketene | p. 725 |
| 1-(Trimethylsilyl)vinyllithium 726 E)-2-(Trimethylsilyl)vinyllithium | p. 729 |
| 1-(Trimethylsilyl)vinylmagnesium Bromide-Copper(I) Iodide | p. 730 |
| Trimethyl{2-[(tributylstannyl)methyl]-2-propenyl}silane | p. 731 |
| Triphenylsilane | p. 733 |
| Tris(dimethylamino)sulfonium Difluorotrimethylsilicate | p. 739 |
| Tris(trimethylsilyl)aluminum | p. 745 |
| Tris(trimethylsilyl)methane | p. 746 |
| Tris(trimethylsilyl)silane | p. 747 |
| Vinyltrimethylsilane | p. 755 |
| List of Contributors | p. 763 |
| Reagent Formula Index | p. 779 |
| Subject Index 785 ??? | |
| Table of Contents provided by Publisher. All Rights Reserved. |
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