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

Galvinoxyl

Br

CH3

NBS

NMP

N+
H
PCC

Cl-CrO3-

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
Hnig's Base
Jones Reagent
Lawesson Reagent
Lindlar Catalyst
Manders 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

(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