General

Reagents and Solvents

Substituents and Protecting Groups

Abbreviation

Term

α

observed optical rotation (in degrees)

δ

chemical shift

anhyd

anhydrous

AO

atomic orbital

aq

aqueous

atm

atmosphere(s)

av

average

bp

boiling point

br

broad (spectral)

calcd

calculated

cat.

catalytic; catalyst (in schemes and tables)

CD

circular dichroism

CI

chemical ionization

cm^–1

wavenumber(s)

Compd

compound (in tables)

concd

concentrated

concn

concentration

Config

configuration (in tables)

COSY

correlation spectroscopy

CV

cyclic voltammetry

d

day(s); doublet (spectral)

d

density

de

diastereomeric excess

DEPT

distortionless enhancement by polarization transfer

dr

diastereomeric ratio

ee

enantiomeric excess

EI

electron impact

eq

equation

equiv

equivalent(s)

er

enantiomeric ratio

ESI

electrospray ionization

ESR

electron spin resonance

FAB

fast atom bombardment

FD

field desorption

FID

flame ionization detector; free induction decay

FT

Fourier transform

g

gram(s)

GC

gas chromatography

h

hour(s)

HOMO

highest occupied molecular orbital

HPLC

high-performance liquid chromatography

HRMS

high-resolution mass spectrometry

Hz

hertz

IR

infrared

J

coupling constant

K

kelvin(s)

L

liter(s)

lit.

literature

LUMO

lowest unoccupied molecular orbital

m

multiplet (spectral)

M

molar (moles per liter)

m/z

mass-to-charge ratio

M⁺

parent molecular ion

MALDI

matrix-assisted laser desorption ionization

max

maximum

MHz

megahertz

min

minute(s); minimum

mL

milliliter

mM

millimolar (millimoles per liter)

mmol

millimole(s)

mol

mole(s)

mol wt

molecular weight

mp

melting point

MS

mass spectrometry; molecular sieves

MW

microwave (in schemes)

N

normal (equivalents per liter)

NMR

nuclear magnetic resonance

NOE

nuclear Overhauser effect

NOESY

nuclear Overhauser effect spectroscopy

Nu

nucleophile

obsd

observed

OD

optical density

op

optical purity

Pa

Pascal

ppm

part(s) per million

q

quartet (spectral)

quin

quintet (spectral)

r.t.

room temperature

redox

reduction–oxidation

Ref.

reference (in tables)

R_f

retention factor (for TLC)

s

singlet (spectral); second(s)

sat.

saturated

sept

septet (spectral)

sext

sextet (spectral)

soln

solution

t

triplet (spectral)

Temp

temperature (in tables)

TLC

thin-layer chromatography

TOF

time-of-flight

Torr

Torr

t_R

retention time (chromatography)

TS

transition state

UV

ultraviolet

v/v

volume per unit volume (volume-to-volume ratio)

vis

visible

vol

volume

w/w

weight per unit weight (weight-to-weight ratio)

wt

weight

Reagents and Solvents

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Abbreviation

Compound Name

acac

acetylacetonate

acetone

acetone

AcOH

acetic acid

Ac₂O

acetic anhydride

AIBN

2,2’-azobis(isobutyronitrile)

alumina

alumina / aluminum oxide

9-BBN-H

9-borabicyclo[3.3.1]nonane

BF₃·OEt₂

boron trifluoride–diethyl ether complex

BINAL-H

2,2’-dihydroxy-1,1’-binaphthyllithium aluminum hydride

BMS

borane–methyl sulfide complex

BOMBr

benzyl bromomethyl ether

BOMCl

benzyl chloromethyl ether

BOPCl

bis(2-oxo-3-oxazolidinyl)phosphinic chloride

BuLi or n-BuLi

n-butyllithium

s-BuLi

sec-butyllithium

t-BuLi

tert-butyllithium

BuOH or n-BuOH

n-butyl alcohol / butan-1-ol

i-BuOH

isobutyl alcohol

s-BuOH

sec-butyl alcohol / butan-2-ol

t-BuOH

tert-butyl alcohol

t-BuOK

potassium tert-butoxide

t-BuOOH

tert-butyl hydroperoxide

cAMP

adenosine cyclic 3’,5’-phosphate

CAN

cerium(IV) ammonium nitrate

CCl₄

carbon tetrachloride / tetrachloromethane

CH₂Cl₂

dichloromethane

CHCl₃

chloroform

CSA

10-camphorsulfonic acid

DABCO

1,4-diazabicyclo[2.2.2]octane

DBN

1,5-diazabicyclo[4.3.0]non-5-ene

DBU

1,8-diazabicyclo[5.4.0]undec-7-ene

DCC

N,N’-dicyclohexylcarbodiimide

DCE

1,2-dichloroethane

DDQ

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DEAD

diethyl azodicarboxylate

DET

diethyl tartrate

DIAD

diisopropyl azodicarboxylate

DIBAL-H

diisobutylaluminum hydride

DIC

diisopropylcarbodiimide

DIPEA

N,N-diisopropylethylamine

DIPT

diisopropyl tartrate

DMAP

4-(N,N-dimethylamino)pyridine

DMDO

dimethyldioxirane

DME

1,2-dimethoxyethane

DMF

N,N-dimethylformamide

DMP

Dess–Martin periodinane

DMPU

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / N,N’-dimethylpropylene urea

DMSO

dimethyl sulfoxide

DNA

deoxyribonucleic acid

DPPA

diphenylphosphoryl azide

DTBB

4,4’-di-tert-butylbiphenyl

EDC or EDCI

N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide

EDTA

ethylenediaminetetraacetic acid

Et₂O

diethyl ether

Et₃N

triethylamine

EtOAc

ethyl acetate

EtOH

ethanol

HMDS

hexamethyldisilazane

HMPA

hexamethylphosphoramide

K₂CO₃

potassium carbonate

KHMDS

potassium hexamethyldisilazide

LAH

lithium aluminum hydride

LDA

lithium diisopropylamide

LHMDS or LiHMDS

lithium hexamethyldisilazide

LTMP

lithium 2,2,6,6-tetramethylpiperidide

MCPBA

m-chloroperoxybenzoic acid

MeCHO

acetaldehyde

MeCN

acetonitrile

MeI

iodomethane

MEK

methyl ethyl ketone

MEMCl

2-methoxyethoxymethyl chloride

MeOH

methanol

MeOTf

methyl trifluoromethanesulfonate

MgSO₄

magnesium sulfate

MOMCl

chloromethyl methyl ether

MoOPh

oxoperoxymolybdenum(pyridine)(hexamethyl phosphoramide)

MS

molecular sieves

MsCl

methanesulfonyl chloride

MsOH

methanesulfonic acid

MTBE

methyl tert-butyl ether

MVK

methyl vinyl ketone

Na₂CO₃

sodium carbonate

Na₂SO₄

sodium sulfate

NaBH₄

sodium borohydride

NaHCO₃

sodium bicarbonate

NaHMDS

sodium hexamethyldisilazide

NBS

N-bromosuccinimide

NCS

N-chlorosuccinimide

NH₄Cl

ammonium chloride

NHS

N-hydroxysuccinimide

NIS

N-iodosuccinimide

NMM

N-methylmorpholine

NMO

N-methylmorpholine N-oxide

NMP

N-methyl-2-pyrrolidinone

PCC

pyridinium chlorochromate

PDC

pyridinium dichromate

PE

petroleum ether

PEG

polyethylene glycol

Ph₃P

triphenylphosphane

PhOH

phenol

PMBCl

p-methoxybenzyl chloride

PMBOH

p-methoxybenzyl alcohol

PPA

poly(phosphoric acid)

PPTS

pyridinium p-toluenesulfonate

PrOH

propanol / propan-1-ol

i-PrOH

isopropyl alcohol / propan-2-ol

PTC

phase transfer catalysis

PTSA

p-toluenesulfonic acid

py

pyridine

RAMP

(R)-1-amino-2-(methoxymethyl)pyrrolidine

Red-Al^®

sodium bis(2-methoxyethoxy)aluminum hydride

SAMP

(S)-1-amino-2-(methoxymethyl)pyrrolidine

SEMCl

2-(trimethylsilyl)ethoxymethyl chloride

TBAB

tetrabutylammonium bromide

TBACl

tetrabutylammonium chloride

TBAF

tetrabutylammonium fluoride

TBSOTf

tert-butyldimethylsilyl trifluoromethanesulfonate

TCNE

tetracyanoethylene

TES

triethylsilane

TESOTf

triethylsilyl trifluoromethanesulfonate

TFA

trifluoroacetic acid

TFAA

trifluoroacetic anhydride

TfOH

trifluoromethanesulfonic acid

THF

tetrahydrofuran

THP

tetrahydropyran

TiCl₄

titanium(IV) chloride

TMEDA

N,N,N’,N’-tetramethylethylenediamine

TMS

tetramethylsilane

TMSCl

trimethylsilyl chloride

TMSIM

1-(trimethylsilyl)imidazole

TMSOTf

trimethylsilyl trifluoromethanesulfonate

TrocCl

2,2,2-trichloroethyl chloroformate

Substituents and Protecting Groups

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Abbreviation

Substituent Name

Ac

acetyl

acac

acetylacetonato

All

allyl

Ar

aryl

9-BBN

9-borabicyclo[3.3.1]nonyl

BINAP

2,2’-bis(diphenylphosphanyl)-1,1’-binaphthyl

Bn

benzyl

Boc

tert-butoxycarbonyl

BOM

benzyloxymethyl

bpy

2,2’-bipyridyl

Bu or n-Bu

n-butyl

i-Bu

isobutyl

s-Bu

sec-butyl

t-Bu

tert-butyl

Bz

benzoyl

Cbz

benzyloxycarbonyl

CDA

cyclohexane-1,2-diacetal

Cp

cyclopentadienyl

Cy

cyclohexyl

DMB

2,4- or 3,4-dimethoxybenzyl / 2,4- or 3,4-dimethoxyphenylmethyl

DMIPS

dimethylisopropylsilyl

DPS or TBDPS

tert-butyldiphenylsilyl

EE

1-ethoxyethyl

Et

ethyl

Fc

ferrocenyl

Fmoc

9-fluorenylmethoxycarbonyl

Me

methyl

MEM

(2-methoxyethoxy)methyl

Mes

mesityl / 2,4,6-trimethylphenyl

MOM

methoxymethyl

Ms

mesyl / methanesulfonyl

Naph

2-naphthyl

PBB

p-bromobenzyl

PCB

p-chlorobenzyl

Ph

phenyl

Phth

phthaloyl

Pr

propyl

i-Pr

isopropyl

PMB

p-methoxybenzyl

PMBM

p-methoxybenzyloxymethyl

PMP

p-methoxyphenyl

Pv

pivaloyl

py

2-pyridyl

R

alkyl

SEM

[2-(trimethylsilyl)ethoxy]methyl

TBDMS or TBS

tert-butyldimethylsilyl

TBDPS or DPS

tert-butyldiphenylsilyl

TCE

2,2,2-trichloroethyl

TES

triethylsilyl

Tf

triflyl / trifluoromethanesulfonyl

THP

tetrahydropyran-2-yl

TIPS

triisopropylsilyl

TMS

trimethylsilyl

Tol

4-methylphenyl

TPS

triphenylsilyl

Tr

trityl / triphenylmethyl

Troc

2,2,2-trichloroethoxycarbonyl

Ts

tosyl / p-toluenesulfonyl

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