Copyright H. J. Reich 2002. ORGANIC CHEMISTRY ACRONYMS. Not included:
peptide protecting groups, inorganic and organometallic ligands, biochemical ...
Copyright H. J. Reich 2002
ORGANIC CHEMISTRY ACRONYMS Not included: peptide protecting groups, inorganic and organometallic ligands, biochemical abbreviations. Ac acac AIBN 9-BBN-H bda BHT BINALH BINAP bipy (bpy) BMS Boc BOM Bs BSA Bz Bn BTAF CAN Cbz cod COT Cp Cp* CSA CSI CTAB DA DABCO DAST DBN DBU DCA DCC DDQ DDT de DEADCAT DET DIBAL Diglyme Dimsyl DIOP diphos DHP DMAc DMAD DMAP DME DMF DMPU DMSO
Acetyl (CH3C=O) Acetylacetonate (ligand) Azobis(isobutyronitrile)--radical initiator N N 9-Borabicyclo[3.3.1]nonane NC CN AIBN Benzylidene Acetone Butylated hydroxy toluene (2,6-di-t-butyl-4-methylphenol) Lithium 2,2'-dihydroxy-1,1'-binaphthylethoxyaluminum hydride O O 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl O 2,2'-bipyridyl SO3H O O Borane Dimethyl Sulfide CSA t-Butyloxycarbonyl (COtC4H9) Crown-4 H Benzyloxymethyl (PhCH2OCH2-alcohol protection) Brosylate (BrC6H4SO2) B N O,N-Bistrimethylsilyl Acetamide N Benzoyl (caution: sometimes used for benzyl) DABCO Benzyl Benzyltrimethylammonium Fluoride 9-BBN Ceric Ammonium Nitrate Carbobenzyloxy (BnOC=O) O Cyclooctadiene Cl-S -NCO Cyclooctatetraene N=C=N O Cyclopentadienyl DCC CSI Pentamethylcyclopentadienyl Camphorsulfonic Acid Chlorosulfonyl Isocyanate N N Cetyltrimethylammonium bromide Diels-Alder Reaction N N 1,4-Diazabicyclo[2.2.2]octane DBN DBU (Diethylamino)sulfur trifluoride Et2NSF3 H 1,5-Diazabicyclo[4.3.0]non-5-ene O PPh2 1,8-Diazabicyclo[5.4.0]undec-7-ene 1,9-Dicyanoanthracene PPh2 O Dicyclohexyl Carbodiimide H 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone DIOP 1,1-Bis(p-chlorophenyl)-2,2,2-trichloroethane N(CH3)2 Diastereomeric excess Diethyl Azodicarboxylate O Diethyl Tartrate DHP (DIBAH) Diisobutylaluminum Hydride N Diethylene glycol dimethyl ether O DMAP Methylsulfinylmethide (MeS(O)CH2NC Cl (dppe) 1,2-Bis(diphenylphosphino)ethane Dihydropyran (O-protection) N,N-Dimethylacetamide (solvent) Dimethyl Acetylenedicarboxylate 4-Dimethylaminopyridine (base catalyst) 1,2-Dimethoxyethane (glyme, solvent) Dimethylformamide (solvent) N,N'-dimethyl-N,N'-propylene urea Dimethyl Sulfoxide (solvent)
Acronyms-1
NC
Cl O DDQ
DMSO2 Dimethyl Sulfone DMTSF Dimethyl(methylthio)sulfonium tetrafluoroborate DNP Dinitrophenylhydrazine DNPBA 2,4-Dinitroperbenzoic acid dppb 1,4-Bis(diphenylphosphino)butane N N dppe (diphos) 1,2-Bis(diphenylphosphino)ethane dppp 1,3-Bis(diphenylphosphino)propane O E Entgegen (opposite, trans) DMPU E Methoxycarbonyl CO2CH3 EDTA Ethylenediaminetetraacetic acid NMe2 ee Enantiomeric Excess O=P NMe2 EE 1-Ethoxyethoxy (alcohol protection) NMe2 en Ethylene Diamine HMPA FC Friedel-Crafts Reaction Fmoc 9-Fluorenylmethoxycarbonyl Fp Cyclopentadienyldicarbonylferrate Li N Glyme 1,2-Dimethoxyethane Galvinoxyl Radical trap HBT Hydroxybenzotriazole LDA HMDS Hexamethyldisilazide HMPA,HMPT Hexamethylphosphorictriamide (solvent, cosolvent) N HSAB Hard-Acid-Soft-Base Li HVZ Hell-Vollhardt-Zelinsky Reaction ("-bromination of carboxylic acids) LiTMP Ipc2BH Bisisopinocampheylborane KDA Potassium Diisopropylamide LAH Lithium Aluminum Hydride (LiAlH4) )2 BH LDA Lithium Diisopropylamide LFER Linear Free Energy Relationship Ipc2BH LHMDS Lithium Hexamethyldisilazide (LiN(SiMe3)2) LICA Lithium N-isopropylcyclohexylamide N LICKOR Lithium-potassium alkoxide reagents N LiTMP Lithium Tetramethylpiperidide N LTA Lead Tetraacetate (Pb(OAc)4) MA Maleic Anhydride HBT OH MCPBA meta-Chloroperoxybenzoic Acid MEM $-Methoxyethoxymethyl (CH3OCH2CH2O-CH2-, alcohol protection) Mes Mesityl (2,4,6-trimethylphenyl) Cl MOM Methoxymethyl (CH3OCH2-, alcohol protection). OOH MoOPH MoO5@Py@HMPA (oxidizing agent) Ms Methanesulfonyl (Mesyl, CH3SO2) O MTPA "-Methoxy-"-trifluoromethylphenylacetic acid (Mosher) MCPBA MTM Methylthiomethyl CH3-S-CH2- (alcohol protection) MVK Methyl Vinyl Ketone (3-Butene-2-one) NBA N-Bromoacetamide NBS, NCS N-Bromo, N-Chlorosuccinimide Nf Nonaflate (C4F9SO2) NIS N-Iodosuccinimide NMO N-Methylmorpholine-N-oxide NMP N-Methylpyrrolidone; solvent Ns p-Nitrobenzenesulfonyl PBB, PCB Polybrominated, Polychlorinated Biphenyls PCC Pyridinium chlorochromate PDC Pyridinium dichromate PG Prostaglandins phen 1,10-Phenanthroline PhthN Phthalimido
Acronyms-2
PMDTA PMB PNB PPA PPTS PTAD PTC Pv Py RT SEM SES Sia2BH TASF TBAF TBDMS TBDPS TBHP TBS TCE TCNE TCNQ TEA TES Tf TFA Thexyl THF THP TIPS TMEDA TMS TMSI Tol TOSMIC TPAP TPP TRIS Trityl Troc Ts TTN WK Z
N,N,N',N'',N''-pentamethyldiethylenetriamine p-Methoxybenzyl para-Nitrobenzoate . O Polyphosphoric Acid Pyridinium p-Toluenesulfonate N-Phenyl-1,2,4-triazolinedione Phase Transfer Catalyst Pivaloyl Pyridine; Solvent, base, catalyst O Room Temperature 2-Trimethylsilylethoxymethoxy (alcohol protection) Trimethylsilylethylsulfonyl (amine protection SO2CH2CH2SiMe3) Disiamylborane (Me2CHMeCH)2BH Tris(dimethylamino)sulfonium difluorotrimethylsilicate Tetra-n-butylammonium fluoride t-Butyldimethylsilyl (alcohol protection) t-Butyldiphenylsilyl (alcohol protection) t-Butylhydroperoxide t-Butyldimethylsilyl (also TBDMS) 2,2,2-Trichloroethyl (alcohol, acid protection) Tetracyanoethylene 7,7,8,8-Tetracyanoquinodimethane Triethylamine Triethylsilyl Triflate (CF3SO2) Trifluoroacetic(yl) Me2CHMe2CTetrahydrofuran; solvent Tetrahydropyran (alcohol protecting group) Triisopropylsilyl (alcohol protection) N,N,N',N'-Tetramethylethylenediamine Tetramethylsilane, also Trimethylsilyl Trimethylsilyl Iodide p-Tolyl p-Toluenesulfonylmethylisocyanide Tetra-n-propylammonium Perruthenate meso-Tetraphenylporphyrin Tris(hydroxymethyl)aminomethane (buffer) Triphenylmethyl Trichloroethyloxycarbonyl (CCl3CH2OC(O)-) Tosyl (p-CH3C6H4SO2) Thallium Trinitrate Wolff-Kishner Reduction Zusammen (together, cis)
Acronyms-3
CH
O
Galvinoxyl
N
O
Br
CH3
NBS
NMP
N+ H PCC
O
N
Cl-CrO3-
N
N TMEDA
Name Reagents and Trade Names Brederick Reagent Burgess Reagent Caro's Acid Colman's Reagent Corey-Kim Reagent Danishefsky's Diene Dess-Martin Periodinane Diazald Eschenmoser's Salt Freons (Fluorohalocarbons) Fremy's Salt Gilman Reagents Hünig's Base Jones Reagent Lawesson Reagent Lindlar Catalyst Mander’s Reagent Meerwein's Salt Mosher Esters Oxone Red-Al Selectride Simmons-Smith Reagent Skellysolve Super Hydride Tebbe's Reagent Viehe's Salt Vilsmeier Reagent Wieland-Miescher Ketone Wilkinson's Catalyst Wittig Reagent
A c OAc O
Dimethoxydimethylaminomethane (amide acetal) MeO2CN-SO2N+(Et)3 (alcohol dehydration) Sulfomonoperacid HOSO2OOH Disodium Iron Tetracarbonyl Dimethyl sulfide-chlorine 1-Methoxy-3-trimethylsiloxybuta-1,3-diene
I OAc
O O Dess-Martin
N-Methyl-N-nitroso-p-toluenesulfonamide (diazomethane) Me2N+=CH2 I- (Mannich reagent) 11 (CFCl3), 12 (CF2Cl2), 13 (CF3Cl), 13B1 (CF3Br), 14 (CF4), 21 (CHFCl2), 22 (CHF2Cl), 23 (CHF3), 114 (CF2ClCF2Cl), 116 (CF3CF3) (KO3S)2NO Lithium Diorganocuprates S S Diisopropylethylamine (base catalyst) MeO P P Chromic acid in acetone S S
Lawesson Pd on CaCO3/PbO Methyl cyanoformate (NCC(=O)OMe Triethyloxonium Fluoroborate (Me3O+ BF4-, methylating reagent) "-Methoxy-"-trifluromethylphenylacetates Potassium monopersulfate (KHSO5) CH2 Sodium bis(2-methoxyethoxy)aluminum Hydride Ti Cl tri-sec-butylborohydride (L = Li, K = potassium) CH2I2-Zn(Cu) Petroleum ether solvents (alkane fractions) Tebbe Sodium Triethylborohydride Cp2Ti(CH2)(Cl)AlMe2 Me2N+=CCl2 ClMe2N+=CHCl Cl-
CH3 Al CH3
O
O
(Ph3P)3RhCl Ph3P=CR2
Wieland-Miescher
Spectroscopy and Separation Acronyms ASIS
Aromatic solvent induced shifts (NMR) Chemical shift (NMR) CD Circular Dichroism CI Chemical Ionization (mass spec) CIDNP Chemically Induced Dynamic Nuclear Polarization CMR Carbon-13 Magnetic Resonance COSY Correlation Spectroscopy (NMR) DEPT Distortionless Enhancement by Polarization Transfer (NMR) DNMR Dynamic NMR EI Electron Impact (MS) ENDOR Electron Nuclear Double Resonance ESR (=EPR) Electron (Paramagnetic) Spin Resonance EXAFS Extended X-Ray Absorption Fine Spectrum EXSY Exchange spectroscopy (NMR saturation transfer) FAB Fast Atom Bombardment (MS) FID Flame Ionization Detecter (VPC) FID Free Induction Decay (NMR) FT Fourier Transform *
Acronyms-4
OMe
GLC HETCOR HMQC HOESY HPLC ICR INDOR INEPT IR J LC LIS MCD MS NMR NOE(SY) OD ORD ORTEP PES Rf ROESY TLC UV VPC XPS
Gas-liquid Chromatography (VPC) Heteronuclear correlation (NMR) Proton detected Heteronuclear Multiquantum Coherence (NMR) Heteronuclear Overhauser Spectroscopy (NMR) High Performance Liquid Chromatography Ion Cyclotron Resonance Internuclear Double Resonance Insensitive Nuclei Enhanced by Polarization Transfer (NMR) Infrared Coupling Constant (NMR) Liquid Chromatography Lanthanide Induced shifts (NMR) Magnetic Circular Dichroism Mass spectrum Nuclear Magnetic Resonance Nuclear Overhauser Effect (Spectroscopy) Optical Density Optical Rotatory Dispersion Oak Ridge Thermal Ellipse Program Photoelectron Spectroscopy Retention Factor (chromatography) Rotating frame Nuclear Overhauser Spectroscopy (NMR) Thin Layer Chromatography Ultraviolet spectroscopy Vapor Phase Chromatography (GLC) (ESCA) X-Ray Photoelectron Spectroscopy
Acronyms-5
