Essential Reagents for Organic Synthesis
Published on 19. July 2016
640 pages
978-1-119-27987-7 (ISBN)
Description
From Boron Trifluoride to Zinc, the 52 most widely used reagents in organic synthesis are described in this unique desktop reference for every organic chemist. The list of reagents contains classics such as N-Bromosuccinimide (NBS) and Trifluoromethanesulfonic Acid side by side with recently developed ones like Pinacolborane and Tetra-n-propylammonium Perruthenate (TPAP).
For each reagent, a concise article provides a brief description of all important reactions for which the reagent is being used, including yields and reaction conditions, an overview of the physical properties of the reagent, its storage conditions, safe handling, laboratory synthesis and purification methods. Advantages and disadvantages of the reagent compared to alternative synthesis methods are also discussed.
Reagents have been hand-picked from among the 5000 reagents contained in EROS, the Encyclopedia of Reagents for Organic Synthesis. Every organic chemist should be familiar with these key reagents that can make almost every reaction work.
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Philip L. Fuchs | André B. Charette | Tomislav Rovis
Essential Reagents for Organic Synthesis
Book
09/2016
Wiley
€116.50
Shipment within 15-20 days
Persons
Professor Philip L. Fuchs from Purdue University, West Lafayette, USA.
Professor André B. Charette from Montréal University, Canada.
Professor Tomislav Rovis from Colorado State University, Fort Collins, USA.
Professor Jeffrey W. Bode from the ETH - Swiss Institute of Technology, Zurich, Switzerland.
Are the current editors of EROS, the Encyclopedia of Reagents for Organic Synthesis.
EROS was founded by Leo Paquette in 1995. Since then it has grown into the largest collection of its kind, covering close to 5,000 different organic-chemical reagents and catalysts.
Content
Preface ix
Short Note on InChIs and InChIKeys xi
General Abbreviations xiii
Bis(dibenzylideneacetone)palladium(0) 2
9-Borabicyclo[3.3.1]nonane Dimer 17
Boron Trifluoride Etherate 27
N-Bromosuccinimide 43
n-Butyllithium 54
N,N[1]-Carbonyl Diimidazole 72
Cerium(IV) Ammonium Nitrate 80
m-Chloroperbenzoic Acid 87
N-Chlorosuccinimide 98
Chlorotrimethylsilane 108
Chlorotris(triphenylphosphine)-rhodium(I) 121
(Diacetoxyiodo)benzene 136
Diazomethane 145
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 152
Diisobutylaluminum Hydride 164
4-Dimethylaminopyridine 170
Dimethyldioxirane 176
1-Ethyl-3-(3[1]-dimethylaminopropyl) carbodiimide Hydrochloride 184
N-Iodosuccinimide 188
Iodotrimethylsilane 194
2-Iodoxybenzoic Acid 206
Lithium Aluminum Hydride 212
Lithium Diisopropylamide 224
Lithium Naphthalenide 241
Manganese Dioxide 248
Osmium Tetroxide 264
Oxalyl Chloride 283
Oxalyl Chloride-Dimethylformamide 288
Ozone 290
Pinacolborane 306
Potassium Hexamethyldisilazide 313
Potassium Monoperoxysulfate 334
Potassium tert-Butoxide 353
Ruthenium(II), Tris(2,2[1]-bipyridine-kappaN1,kappaN1[1])-, (OC-6-11)- 370
Samarium(II) Iodide 378
Scandium Trifluoromethanesulfonate 388
Sodium Azide 398
Sodium Borohydride 406
Sodium Cyanoborohydride 419
Sodium Hexamethyldisilazide 428
Sodium Hydride 438
Sodium Periodate 447
Tetrabutylammonium Fluoride 458
Tetrakis(triphenylphosphine)-palladium(0) 467
Tetra-n-propylammonium Perruthenate 476
p-Toluenesulfonyl Chloride 480
Triethylsilane 489
Trifluoromethanesulfonic Acid 498
Trifluoromethanesulfonic Anhydride 507
Trimethylsilyl Trifluoromethanesulfonate 524
Trimethylsilyldiazomethane 543
Zinc-Acetic Acid 554
List of Contributors 000
Subject Index 000
Ac acetyl acac acetylacetonate AIBN 2,2´-azobisisobutyronitrile Ar aryl BBN borabicyclo[3.3.1]nonane BCME dis(chloromethyl)ether BHT butylated hydroxytoluene (2,6-di-t-butyl-p-cresol) BINAL-H 2,2´-dihydroxy-1,1´-binaphthyl-lithium aluminum hydride BINAP 2,2´-bis(diphenylphosphino)-1,1´-binaphthyl BINOL 1,1´-bi-2,2´-naphthol bipy 2,2´-bipyridyl BMS borane-dimethyl sulfide Bn benzyl Boc t-butoxycarbonyl BOM benzyloxymethyl bp boiling point Bs brosyl (4-bromobenzenesulfonyl) BSA N,O-bis(trimethylsilyl)acetamide Bu n-butyl Bz benzoyl CAN cerium(IV) ammonium nitrate Cbz benzyloxycarbonyl CDI N,N´-carbonyldiimidazole CHIRAPHOS 2,3-bis(diphenylphosphino)butane Chx =Cy cod cyclooctadiene cot cyclooctatetraene Cp cyclopentadienyl CRA complex reducing agent CSA 10-camphorsulfonic acid CSI chlorosulfonyl isocyanate Cy cyclohexyl d density DABCO 1,4-diazabicyclo[2.2.2]octane DAST N,N´-diethylaminosulfur trifluoride dba dibenzylideneacetone DBAD di-t-butyl azodicarboxylate DBN 1,5-diazabicyclo[4.3.0]non-5-ene DBU 1,8-diazabicyclo[5.4.0]undec-7-ene DCC N,N´-dicyclohexylcarbodiimide DCME dichloromethyl methyl ether DDO dimethyldioxirane DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone de diastereomeric excess DEAD diethyl azodicarboxylate DET diethyl tartrate DIBAL diisobutylaluminum hydride DIEA =DIPEA DIOP 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis-(diphenylphosphino)butane DIPEA diisopropylethylamine diphos =dppe DIPT diisopropyl tartrate DMA dimethylacetamide DMAD dimethyl acetylenedicarboxylate DMAP 4-(dimethylamino)pyridine DME 1,2-dimethoxyethane DMF dimethylformamide dmg dimethylglyoximato DMPU N,N´-dimethylpropyleneurea DMS dimethyl sulfide DMSO dimethyl sulfoxide DMTSF dimethyl(methylthio) sulfonium tetrafluoroborate dppb 1,4-bis(diphenylphosphino)butane dppe 1,2-bis(diphenylphosphino)ethane dppf 1,1´-bis(diphenylphosphino)ferrocene dppp 1,3-bis(diphenylphosphino)propane DTBP di-t-butyl peroxide EDA ethyl diazoacetate EDC 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide EDCI =EDC ee enantiomeric excess EE 1-ethoxyethyl Et ethyl ETSA ethyl trimethylsilylacetate EWG electron withdrawing group Fc ferrocenyl Fmoc 9-fluorenylmethoxycarbonyl fp flash point Hex n-hexyl HMDS hexamethyldisilazane HMPA hexamethylphosphoric triamide HOBt l-hydroxybenzotriazole HOBT =HOBt HOSu N-hydroxysuccinimide Im imidazole (imidazolyl) Ipc isopinocampheyl IR infrared KHDMS potassium hexamethyldisilazide LAH lithium aluminum hydride LD50 dose that is lethal to 50% of test subjects LDA lithium diisopropylamide LDMAN lithium 1-(dimethylamino)naphthalenide LHMDS =LiHMDS LICA lithium isopropylcyclohexylamide LiHMDS lithium hexamethyldisilazide LiTMP lithium 2,2,6,6-tetramethylpiperidide LTMP =LiTMP LTA lead tetraacetate lut lutidine m-CPBA m-chloroperbenzoic acid MA maleic anhydride MAD methylaluminum bis(2,6-di-t-butyl-4-methylphenoxide) MAT methylaluminum bis(2,4,6-tri-t-butylphenoxide) Me methyl MEK methyl ethyl ketone MEM (2-methoxyethoxy)methyl MIC methyl isocyanate MMPP magnesium monoperoxyphthalate MOM methoxymethyl MoOPH oxodiperoxomolybdenum(pyridine)-(hexamethylphosphoric triamide) mp melting point MPM =PMB Ms mesyl (methanesulfonyl) MS mass spectrometry; molecular sieves MTBE methyl t-butyl ether MTM methylthiomethyl MVK methyl vinyl ketone n refractive index NaHDMS sodium hexamethyldisilazide Naph naphthyl NBA N-bromoacetamide nbd norbornadiene (bicyclo[2.2.1]hepta-2,5-diene) NBS N-bromosuccinimide NCS N-chlorosuccinimide NIS N-iodosuccinimide NMO N-methylmorpholine N-oxide NMP N-methyl-2-pyrrolidinone NMR nuclear magnetic resonance NORPHOS bis(diphenylphosphino)bicyclo[2.2.1]-hept-5-ene Np =Naph PCC pyridinium chlorochromate PDC pyridinium...
General Abbreviations
Ac acetyl acac acetylacetonate AIBN 2,2´-azobisisobutyronitrile Ar aryl BBN borabicyclo[3.3.1]nonane BCME dis(chloromethyl)ether BHT butylated hydroxytoluene (2,6-di-t-butyl-p-cresol) BINAL-H 2,2´-dihydroxy-1,1´-binaphthyl-lithium aluminum hydride BINAP 2,2´-bis(diphenylphosphino)-1,1´-binaphthyl BINOL 1,1´-bi-2,2´-naphthol bipy 2,2´-bipyridyl BMS borane-dimethyl sulfide Bn benzyl Boc t-butoxycarbonyl BOM benzyloxymethyl bp boiling point Bs brosyl (4-bromobenzenesulfonyl) BSA N,O-bis(trimethylsilyl)acetamide Bu n-butyl Bz benzoyl CAN cerium(IV) ammonium nitrate Cbz benzyloxycarbonyl CDI N,N´-carbonyldiimidazole CHIRAPHOS 2,3-bis(diphenylphosphino)butane Chx =Cy cod cyclooctadiene cot cyclooctatetraene Cp cyclopentadienyl CRA complex reducing agent CSA 10-camphorsulfonic acid CSI chlorosulfonyl isocyanate Cy cyclohexyl d density DABCO 1,4-diazabicyclo[2.2.2]octane DAST N,N´-diethylaminosulfur trifluoride dba dibenzylideneacetone DBAD di-t-butyl azodicarboxylate DBN 1,5-diazabicyclo[4.3.0]non-5-ene DBU 1,8-diazabicyclo[5.4.0]undec-7-ene DCC N,N´-dicyclohexylcarbodiimide DCME dichloromethyl methyl ether DDO dimethyldioxirane DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone de diastereomeric excess DEAD diethyl azodicarboxylate DET diethyl tartrate DIBAL diisobutylaluminum hydride DIEA =DIPEA DIOP 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis-(diphenylphosphino)butane DIPEA diisopropylethylamine diphos =dppe DIPT diisopropyl tartrate DMA dimethylacetamide DMAD dimethyl acetylenedicarboxylate DMAP 4-(dimethylamino)pyridine DME 1,2-dimethoxyethane DMF dimethylformamide dmg dimethylglyoximato DMPU N,N´-dimethylpropyleneurea DMS dimethyl sulfide DMSO dimethyl sulfoxide DMTSF dimethyl(methylthio) sulfonium tetrafluoroborate dppb 1,4-bis(diphenylphosphino)butane dppe 1,2-bis(diphenylphosphino)ethane dppf 1,1´-bis(diphenylphosphino)ferrocene dppp 1,3-bis(diphenylphosphino)propane DTBP di-t-butyl peroxide EDA ethyl diazoacetate EDC 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide EDCI =EDC ee enantiomeric excess EE 1-ethoxyethyl Et ethyl ETSA ethyl trimethylsilylacetate EWG electron withdrawing group Fc ferrocenyl Fmoc 9-fluorenylmethoxycarbonyl fp flash point Hex n-hexyl HMDS hexamethyldisilazane HMPA hexamethylphosphoric triamide HOBt l-hydroxybenzotriazole HOBT =HOBt HOSu N-hydroxysuccinimide Im imidazole (imidazolyl) Ipc isopinocampheyl IR infrared KHDMS potassium hexamethyldisilazide LAH lithium aluminum hydride LD50 dose that is lethal to 50% of test subjects LDA lithium diisopropylamide LDMAN lithium 1-(dimethylamino)naphthalenide LHMDS =LiHMDS LICA lithium isopropylcyclohexylamide LiHMDS lithium hexamethyldisilazide LiTMP lithium 2,2,6,6-tetramethylpiperidide LTMP =LiTMP LTA lead tetraacetate lut lutidine m-CPBA m-chloroperbenzoic acid MA maleic anhydride MAD methylaluminum bis(2,6-di-t-butyl-4-methylphenoxide) MAT methylaluminum bis(2,4,6-tri-t-butylphenoxide) Me methyl MEK methyl ethyl ketone MEM (2-methoxyethoxy)methyl MIC methyl isocyanate MMPP magnesium monoperoxyphthalate MOM methoxymethyl MoOPH oxodiperoxomolybdenum(pyridine)-(hexamethylphosphoric triamide) mp melting point MPM =PMB Ms mesyl (methanesulfonyl) MS mass spectrometry; molecular sieves MTBE methyl t-butyl ether MTM methylthiomethyl MVK methyl vinyl ketone n refractive index NaHDMS sodium hexamethyldisilazide Naph naphthyl NBA N-bromoacetamide nbd norbornadiene (bicyclo[2.2.1]hepta-2,5-diene) NBS N-bromosuccinimide NCS N-chlorosuccinimide NIS N-iodosuccinimide NMO N-methylmorpholine N-oxide NMP N-methyl-2-pyrrolidinone NMR nuclear magnetic resonance NORPHOS bis(diphenylphosphino)bicyclo[2.2.1]-hept-5-ene Np =Naph PCC pyridinium chlorochromate PDC pyridinium...
