Acronyms-1

N NCNNC

AIBN

B

H

9-BBN

DABCO

NN

Cl-SO

O-NCO

CSI DCC

N=C=N

DBN

N

N

DBU

N

N

DHP

O

DMAPN

N(CH3)2

DDQ

O

ONC

NC Cl

Cl

Crown-4

O O

OOSO3HO

DIOP

O

O

PPh2

PPh2

H

H

CSA

Copyright H. J. Reich 2002ORGANIC CHEMISTRY ACRONYMS

Not included: peptide protecting groups, inorganic and organometallic ligands, biochemical abbreviations.

Ac Acetyl (CH3C=O)acac Acetylacetonate (ligand)AIBN Azobis(isobutyronitrile)--radical initiator9-BBN-H 9-Borabicyclo[3.3.1]nonanebda Benzylidene AcetoneBHT Butylated hydroxy toluene (2,6-di-t-butyl-4-methylphenol)BINALH Lithium 2,2'-dihydroxy-1,1'-binaphthylethoxyaluminum hydrideBINAP 2,2'-Bis(diphenylphosphino)-1,1'-binaphthylbipy (bpy) 2,2'-bipyridylBMS Borane Dimethyl SulfideBoc t-Butyloxycarbonyl (COtC4H9)BOM Benzyloxymethyl (PhCH2OCH2-alcohol protection)Bs Brosylate (BrC6H4SO2)BSA O,N-Bistrimethylsilyl AcetamideBz Benzoyl (caution: sometimes used for benzyl)Bn BenzylBTAF Benzyltrimethylammonium FluorideCAN Ceric Ammonium NitrateCbz Carbobenzyloxy (BnOC=O)cod CyclooctadieneCOT CyclooctatetraeneCp CyclopentadienylCp* PentamethylcyclopentadienylCSA Camphorsulfonic AcidCSI Chlorosulfonyl IsocyanateCTAB Cetyltrimethylammonium bromideDA Diels-Alder ReactionDABCO 1,4-Diazabicyclo[2.2.2]octaneDAST (Diethylamino)sulfur trifluoride Et2NSF3DBN 1,5-Diazabicyclo[4.3.0]non-5-eneDBU 1,8-Diazabicyclo[5.4.0]undec-7-eneDCA 1,9-DicyanoanthraceneDCC Dicyclohexyl CarbodiimideDDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneDDT 1,1-Bis(p-chlorophenyl)-2,2,2-trichloroethanede Diastereomeric excessDEADCAT Diethyl AzodicarboxylateDET Diethyl TartrateDIBAL (DIBAH) Diisobutylaluminum HydrideDiglyme Diethylene glycol dimethyl etherDimsyl Methylsulfinylmethide (MeS(O)CH2

-

DIOPdiphos (dppe) 1,2-Bis(diphenylphosphino)ethaneDHP Dihydropyran (O-protection)DMAc N,N-Dimethylacetamide (solvent)DMAD Dimethyl AcetylenedicarboxylateDMAP 4-Dimethylaminopyridine (base catalyst)DME 1,2-Dimethoxyethane (glyme, solvent)DMF Dimethylformamide (solvent)DMPU N,N'-dimethyl-N,N'-propylene ureaDMSO Dimethyl Sulfoxide (solvent)

Acronyms-2

HMPA

O=PNMe2

NMe2NMe2

LDA

Li N

MCPBA

OOH

O

LiTMP

N

Li

DMPU

N N

O

Cl

NN

N

HBT OH

Ipc2BH

BH)2

DMSO2 Dimethyl SulfoneDMTSF Dimethyl(methylthio)sulfonium tetrafluoroborateDNP DinitrophenylhydrazineDNPBA 2,4-Dinitroperbenzoic aciddppb 1,4-Bis(diphenylphosphino)butanedppe (diphos) 1,2-Bis(diphenylphosphino)ethanedppp 1,3-Bis(diphenylphosphino)propaneE Entgegen (opposite, trans)E Methoxycarbonyl CO2CH3EDTA Ethylenediaminetetraacetic acidee Enantiomeric ExcessEE 1-Ethoxyethoxy (alcohol protection)en Ethylene DiamineFC Friedel-Crafts ReactionFmoc 9-FluorenylmethoxycarbonylFp CyclopentadienyldicarbonylferrateGlyme 1,2-DimethoxyethaneGalvinoxyl Radical trapHBT HydroxybenzotriazoleHMDS HexamethyldisilazideHMPA,HMPT Hexamethylphosphorictriamide (solvent, cosolvent)HSAB Hard-Acid-Soft-BaseHVZ Hell-Vollhardt-Zelinsky Reaction ("-bromination of carboxylic acids)Ipc2BH BisisopinocampheylboraneKDA Potassium DiisopropylamideLAH Lithium Aluminum Hydride (LiAlH4)LDA Lithium Diisopropylamide LFER Linear Free Energy RelationshipLHMDS Lithium Hexamethyldisilazide (LiN(SiMe3)2)LICA Lithium N-isopropylcyclohexylamideLICKOR Lithium-potassium alkoxide reagentsLiTMP Lithium TetramethylpiperidideLTA Lead Tetraacetate (Pb(OAc)4)MA Maleic AnhydrideMCPBA meta-Chloroperoxybenzoic AcidMEM $-Methoxyethoxymethyl (CH3OCH2CH2O-CH2-, alcohol protection)Mes Mesityl (2,4,6-trimethylphenyl)MOM Methoxymethyl (CH3OCH2-, alcohol protection).MoOPH MoO5@Py@HMPA (oxidizing agent)Ms Methanesulfonyl (Mesyl, CH3SO2)MTPA "-Methoxy-"-trifluoromethylphenylacetic acid (Mosher)MTM Methylthiomethyl CH3-S-CH2- (alcohol protection)MVK Methyl Vinyl Ketone (3-Butene-2-one)NBA N-BromoacetamideNBS, NCS N-Bromo, N-ChlorosuccinimideNf Nonaflate (C4F9SO2)NIS N-IodosuccinimideNMO N-Methylmorpholine-N-oxideNMP N-Methylpyrrolidone; solventNs p-Nitrobenzenesulfonyl PBB, PCB Polybrominated, Polychlorinated BiphenylsPCC Pyridinium chlorochromatePDC Pyridinium dichromatePG Prostaglandinsphen 1,10-PhenanthrolinePhthN Phthalimido

Acronyms-3

NBS

N OO

Br

NMP

N O

CH3

PCC

N

H+ Cl-CrO3

-

TMEDA

N N

Galvinoxyl

CH O.O

PMDTA N,N,N',N'',N''-pentamethyldiethylenetriaminePMB p-MethoxybenzylPNB para-NitrobenzoatePPA Polyphosphoric AcidPPTS Pyridinium p-ToluenesulfonatePTAD N-Phenyl-1,2,4-triazolinedionePTC Phase Transfer CatalystPv PivaloylPy Pyridine; Solvent, base, catalystRT Room TemperatureSEM 2-Trimethylsilylethoxymethoxy (alcohol protection)SES Trimethylsilylethylsulfonyl (amine protection SO2CH2CH2SiMe3)Sia2BH Disiamylborane (Me2CHMeCH)2BHTASF Tris(dimethylamino)sulfonium difluorotrimethylsilicateTBAF Tetra-n-butylammonium fluorideTBDMS t-Butyldimethylsilyl (alcohol protection)TBDPS t-Butyldiphenylsilyl (alcohol protection)TBHP t-ButylhydroperoxideTBS t-Butyldimethylsilyl (also TBDMS)TCE 2,2,2-Trichloroethyl (alcohol, acid protection)TCNE TetracyanoethyleneTCNQ 7,7,8,8-TetracyanoquinodimethaneTEA TriethylamineTES TriethylsilylTf Triflate (CF3SO2)TFA Trifluoroacetic(yl)Thexyl Me2CHMe2C-THF Tetrahydrofuran; solventTHP Tetrahydropyran (alcohol protecting group)TIPS Triisopropylsilyl (alcohol protection)TMEDA N,N,N',N'-Tetramethylethylenediamine TMS Tetramethylsilane, also TrimethylsilylTMSI Trimethylsilyl IodideTol p-TolylTOSMIC p-ToluenesulfonylmethylisocyanideTPAP Tetra-n-propylammonium PerruthenateTPP meso-TetraphenylporphyrinTRIS Tris(hydroxymethyl)aminomethane (buffer)Trityl TriphenylmethylTroc Trichloroethyloxycarbonyl (CCl3CH2OC(O)-)Ts Tosyl (p-CH3C6H4SO2)TTN Thallium TrinitrateWK Wolff-Kishner ReductionZ Zusammen (together, cis)

Acronyms-4

Dess-Martin

I

OO

OAc

OAc

OcA

Lawesson

MeO PS

PS

OMe

S

S

Tebbe

TiCH2

ClAl

CH3

CH3

Wieland-Miescher

O

O

Name Reagents and Trade Names

Brederick Reagent Dimethoxydimethylaminomethane (amide acetal)Burgess Reagent MeO2CN-SO2N+(Et)3 (alcohol dehydration)Caro's Acid Sulfomonoperacid HOSO2OOHColman's Reagent Disodium Iron TetracarbonylCorey-Kim Reagent Dimethyl sulfide-chlorineDanishefsky's Diene 1-Methoxy-3-trimethylsiloxybuta-1,3-dieneDess-Martin PeriodinaneDiazald N-Methyl-N-nitroso-p-toluenesulfonamide (diazomethane)Eschenmoser's Salt Me2N+=CH2 I- (Mannich reagent)Freons (Fluorohalocarbons) 11 (CFCl3), 12 (CF2Cl2), 13 (CF3Cl), 13B1 (CF3Br), 14 (CF4), 21 (CHFCl2), 22

(CHF2Cl), 23 (CHF3), 114 (CF2ClCF2Cl), 116 (CF3CF3)Fremy's Salt (KO3S)2NOGilman Reagents Lithium DiorganocupratesHünig's Base Diisopropylethylamine (base catalyst)Jones Reagent Chromic acid in acetoneLawesson ReagentLindlar Catalyst Pd on CaCO3/PbOMander’s Reagent Methyl cyanoformate (NCC(=O)OMeMeerwein's Salt Triethyloxonium Fluoroborate (Me3O+ BF4

-, methylating reagent)Mosher Esters "-Methoxy-"-trifluromethylphenylacetatesOxone Potassium monopersulfate (KHSO5)Red-Al Sodium bis(2-methoxyethoxy)aluminum HydrideSelectride tri-sec-butylborohydride (L = Li, K = potassium)Simmons-Smith Reagent CH2I2-Zn(Cu)Skellysolve Petroleum ether solvents (alkane fractions)Super Hydride Sodium TriethylborohydrideTebbe's Reagent Cp2Ti(CH2)(Cl)AlMe2Viehe's Salt Me2N+=CCl2 Cl-

Vilsmeier Reagent Me2N+=CHCl Cl-

Wieland-Miescher KetoneWilkinson's Catalyst (Ph3P)3RhClWittig Reagent Ph3P=CR2

Spectroscopy and Separation Acronyms

ASIS Aromatic solvent induced shifts (NMR)* Chemical shift (NMR)CD Circular DichroismCI Chemical Ionization (mass spec)CIDNP Chemically Induced Dynamic Nuclear PolarizationCMR Carbon-13 Magnetic ResonanceCOSY Correlation Spectroscopy (NMR)DEPT Distortionless Enhancement by Polarization Transfer (NMR)DNMR Dynamic NMREI Electron Impact (MS)ENDOR Electron Nuclear Double ResonanceESR (=EPR) Electron (Paramagnetic) Spin ResonanceEXAFS Extended X-Ray Absorption Fine SpectrumEXSY Exchange spectroscopy (NMR saturation transfer)FAB Fast Atom Bombardment (MS)FID Flame Ionization Detecter (VPC)FID Free Induction Decay (NMR)FT Fourier Transform

Acronyms-5

GLC Gas-liquid Chromatography (VPC)HETCOR Heteronuclear correlation (NMR)HMQC Proton detected Heteronuclear Multiquantum Coherence (NMR)HOESY Heteronuclear Overhauser Spectroscopy (NMR)HPLC High Performance Liquid ChromatographyICR Ion Cyclotron ResonanceINDOR Internuclear Double ResonanceINEPT Insensitive Nuclei Enhanced by Polarization Transfer (NMR)IR InfraredJ Coupling Constant (NMR)LC Liquid ChromatographyLIS Lanthanide Induced shifts (NMR)MCD Magnetic Circular DichroismMS Mass spectrumNMR Nuclear Magnetic ResonanceNOE(SY) Nuclear Overhauser Effect (Spectroscopy)OD Optical DensityORD Optical Rotatory DispersionORTEP Oak Ridge Thermal Ellipse ProgramPES Photoelectron SpectroscopyRf Retention Factor (chromatography)ROESY Rotating frame Nuclear Overhauser Spectroscopy (NMR)TLC Thin Layer ChromatographyUV Ultraviolet spectroscopyVPC Vapor Phase Chromatography (GLC)XPS (ESCA) X-Ray Photoelectron Spectroscopy