V. LIST OF ABBREVIATIONS
V. LIST OF ABBREVIATIONS
V. LIST OF ABBREVIATIONS
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TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
V. <strong>LIST</strong> <strong>OF</strong> <strong>ABBREVIATIONS</strong><br />
Abbreviation Chemical Name Chemical Structure<br />
O<br />
18-Cr-6<br />
18-crown-6<br />
O<br />
O<br />
O<br />
O<br />
O<br />
Ac<br />
acetyl<br />
O<br />
acac<br />
acetylacetonyl<br />
O<br />
O<br />
AA asymmetric aminohydroxylation NA<br />
AD asymmetric dihydroxylation NA<br />
ad<br />
adamantyl<br />
ADDP 1,1'-(azodicarbonyl)dipiperidine N N<br />
N<br />
O<br />
O<br />
N<br />
ADMET acyclic diene metathesis polymerization NA<br />
O<br />
acaen<br />
N,N’-bis(1-methyl-3-oxobutylidene)ethylenediamine<br />
O<br />
N<br />
N<br />
AIBN 2,2'-azo bisisobutyronitrile N N<br />
N<br />
N<br />
Alloc<br />
allyloxycarbonyl<br />
O<br />
O<br />
Am<br />
amyl (n-pentyl)<br />
An p-anisyl O<br />
ANRORC anionic ring-opening ring-closing NA<br />
aq aqueous NA<br />
O<br />
AQN<br />
anthraquinone<br />
O<br />
Ar<br />
aryl (substituted aromatic ring)<br />
NA<br />
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Abbreviation Chemical Name Chemical Structure<br />
ATD<br />
aluminum tris(2,6-di-tert-butyl-4-methylphenoxide)<br />
Al<br />
O<br />
atm 1 atmosphere = 10 5 Pa (pressure) NA<br />
3<br />
Ph<br />
ATPH<br />
aluminum tris(2,6-diphenylphenoxide)<br />
Al<br />
O<br />
Ph<br />
3<br />
BBN (9-BBN)<br />
9-borabicyclo[3.3.1]nonane (9-BBN)<br />
H<br />
B<br />
B<br />
9-borabicyclo[3.3.1]nonyl<br />
B<br />
BCME bis(chloromethyl)ether Cl O<br />
Cl<br />
O<br />
BCN<br />
N-benzyloxycarbonyloxy-5-norbornene-2,3-<br />
dicarboximide<br />
O<br />
N<br />
O<br />
O<br />
O<br />
BDPP<br />
(2R, 4R) or (2S, 4S) bis(diphenylphosphino)pentane<br />
Ph 2 P PPh 2<br />
(R)<br />
(R)<br />
BER borohydride exchange resin NA<br />
OH<br />
BHT<br />
2,6-di-t-butyl-p-cresol (butylated hydroxytoluene)<br />
BICP<br />
2(R)-2’(R)-bis(dipenylphosphino)-1(R),1’(R)-<br />
dicyclopentane<br />
(R) (R)<br />
(R)<br />
(R)<br />
Ph 2 P PPh 2<br />
BINAL-H<br />
2,2'-dihydroxy-1,1'-binaphthyl lithium aluminum<br />
hydride<br />
O H<br />
O Al H<br />
Li<br />
BINAP 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl PPh 2<br />
PPh 2<br />
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Abbreviation Chemical Name Chemical Structure<br />
BINOL<br />
1,1'-bi-2,2'-naphthol<br />
OH<br />
OH<br />
Bip<br />
biphenyl-4-sulfonyl<br />
O<br />
S<br />
O<br />
bipy<br />
2,2'-bipyridyl<br />
N<br />
N<br />
BLA<br />
Brönsted acid assisted chiral Lewis acid<br />
NA<br />
bmin 1-butyl-3-methylimidazolium cation<br />
N N<br />
BMS<br />
Borane-dimethyl sulfide complex<br />
H 3<br />
B SMe 2<br />
Bn<br />
benzyl<br />
O<br />
BNAH 1-benzyl-1,4-dihydronicotinamide N<br />
NH 2<br />
BOB<br />
4-benzyloxybutyryl<br />
O<br />
O<br />
Boc<br />
t-butoxycarbonyl<br />
O<br />
O<br />
BOM<br />
benzyloxymethyl<br />
O<br />
BOP-Cl<br />
bis(2-oxo-3-oxazolidinyl)phosphinic chloride<br />
O<br />
O<br />
O Cl<br />
P<br />
N N<br />
O<br />
O<br />
bp boiling point NA<br />
BPD<br />
bis(pinacolato)diboron<br />
O<br />
O<br />
B<br />
B<br />
O<br />
O<br />
O<br />
BPO<br />
benzoyl peroxide<br />
O<br />
Ph<br />
O<br />
O<br />
Ph<br />
BPS (TBDPS) t-butyldiphenylsilyl<br />
Si<br />
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Abbreviation Chemical Name Chemical Structure<br />
BQ benzoquinone O O<br />
Bs brosyl =<br />
(4-bromobenzenesulfonyl)<br />
O<br />
S<br />
O<br />
Br<br />
BSA<br />
N,O-bis(trimethylsilyl)acetamide<br />
Si<br />
N<br />
O<br />
Si<br />
BSA Bovine serum albumin NA<br />
Bt<br />
1- or 2-benzotriazolyl<br />
N<br />
N<br />
N<br />
BTAF benzyltrimethylammonium fluoride N<br />
F<br />
BTEA benzyltriethylammonium N<br />
BTEAC benzyltriethylammonium chloride N<br />
Cl<br />
BTFP<br />
3-bromo-1,1,1-trifluoro-propan-2-one<br />
O<br />
Br<br />
F<br />
F<br />
F<br />
BTMA benzyltrimethylammonium N<br />
BTMSA bis(trimethylsilyl) acetylene<br />
Si Si<br />
BTS<br />
bis(trimethylsilyl) sulfate<br />
O<br />
O<br />
Si S Si<br />
O<br />
O<br />
BTSA<br />
benzothiazole 2-sulfonic acid<br />
HO<br />
O<br />
S<br />
O<br />
S<br />
N<br />
BTSP<br />
bis(trimethylsilyl) peroxide<br />
O Si<br />
Si O<br />
Bz<br />
benzoyl<br />
O<br />
Bu ( n Bu)<br />
n-butyl<br />
c cyclo NA<br />
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Abbreviation Chemical Name Chemical Structure<br />
ca<br />
circa<br />
NA<br />
(approximately)<br />
CA chloroacetyl<br />
O<br />
cerium(IV) ammonium nitrate (cericammonium<br />
CAN<br />
nitrate)<br />
cat. catalytic NA<br />
Cl<br />
Ce(NH 4 ) 2 (NO 3 ) 6<br />
CB<br />
catecholborane<br />
O<br />
HB<br />
O<br />
H<br />
Ph Ph<br />
CBS<br />
Corey-Bakshi-Shibata reagent<br />
N<br />
B<br />
O<br />
R<br />
R = H, alkyl<br />
Cbz (Z)<br />
benzyloxycarbonyl<br />
O<br />
O<br />
cc. or conc. concentrated NA<br />
CCE constant current electrolysis NA<br />
O<br />
CDI<br />
carbonyl diimidazole<br />
N<br />
N<br />
N<br />
N<br />
CHD<br />
1,3 or 1,4-cyclohexadiene<br />
1,3-CHD<br />
1,4-CHD<br />
CHIRAPHOS<br />
2,3-bis(diphenylphosphino)butane<br />
Ph<br />
P<br />
Ph<br />
(S)<br />
(S)<br />
Ph<br />
P<br />
Ph<br />
Chx (Cy)<br />
cyclohexyl<br />
Cl<br />
CIP<br />
2-chloro-1,3-dimethylimidazolidinium<br />
hexafluorophosphate<br />
CM (XMET) cross metathesis NA<br />
N<br />
NH<br />
PF 6<br />
CMMP cyanomethylenetrimethyl phosphorane P<br />
N<br />
COD<br />
1,5-cyclooctadiene<br />
COT<br />
1,3,5-cyclooctatriene<br />
Cp<br />
cyclopentadienyl<br />
O<br />
CPTS<br />
collidinium-p-toluenesulfonate<br />
S O<br />
O<br />
H<br />
N<br />
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Abbreviation Chemical Name Chemical Structure<br />
CRA<br />
Cr-PILC<br />
complex reducing agent<br />
chromium-pillared clay catalyst<br />
NA<br />
NA<br />
CSA<br />
camphorsufonic acid<br />
O<br />
SO 3 H<br />
CSI<br />
chlorosulfonyl isocyanate<br />
O<br />
N<br />
S C<br />
Cl<br />
O<br />
O<br />
CTAB<br />
cetyl trimethylammonium bromide<br />
N<br />
Br<br />
CTACl<br />
cetyl trimethylammonium chloride<br />
N<br />
Cl<br />
C 15 H 31<br />
CTAP<br />
cetyl trimethylammonium permanganate<br />
N MnO 4<br />
C 15 H 31<br />
Δ heat NA<br />
d days (length of reaction time) NA<br />
DABCO<br />
1,4-diazabicyclo[2.2.2]octane<br />
N<br />
N<br />
N<br />
N<br />
DAST diethylaminosulfur trifluoride F S N<br />
F<br />
F<br />
DATMP<br />
diethylaluminum 2,2,6,6-tetramethylpiperidide<br />
N<br />
AlEt 2<br />
DBA (dba)<br />
dibenzylideneacetone<br />
Ph<br />
Ph<br />
O<br />
O<br />
DBAD di-tert-butylazodicarboxylate N<br />
O N<br />
O<br />
O<br />
O<br />
DBI dibromoisocyanuric acid N<br />
Br<br />
N<br />
Br<br />
O<br />
NH<br />
O<br />
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Abbreviation Chemical Name Chemical Structure<br />
O<br />
O<br />
DBM<br />
dibenzoylmethane<br />
DBN<br />
1,5-diazabicyclo[4.3.0]non-5-ene<br />
8<br />
9<br />
7<br />
1 2 N<br />
3<br />
6 N<br />
4<br />
5<br />
DBS<br />
dibenzosuberyl<br />
DBU<br />
1,8-diazabicyclo[5.4.0]undec-7-ene<br />
10<br />
9<br />
11<br />
N<br />
8<br />
1 2 3<br />
N<br />
4<br />
7 5<br />
6<br />
CN<br />
DCA<br />
9,10-dicyanoanthracene<br />
CN<br />
Cl<br />
DCB 1,2-dichlorobenzene<br />
Cl<br />
DCC<br />
dicyclohexylcarbodiimide<br />
N C<br />
N<br />
DCE<br />
1,1-dichloroethane<br />
Cl<br />
Cl<br />
DCM dichloromethane CH 2 Cl 2<br />
CN<br />
DCN<br />
1,4-dicyanonaphthalene<br />
CN<br />
Dcpm<br />
dicyclopropylmethyl<br />
DCU<br />
N,N’-dicyclohexylurea<br />
O<br />
N<br />
H<br />
N<br />
H<br />
O<br />
DDQ<br />
2,3-dichloro-5,6-dicyano-1,4-benzoquinone<br />
NC<br />
NC<br />
O<br />
Cl<br />
Cl<br />
de<br />
diastereomeric excess<br />
NA<br />
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Abbreviation Chemical Name Chemical Structure<br />
DEAD diethyl azodicarboxylate N N<br />
O<br />
O<br />
O<br />
O<br />
DEIPS diethylisopropylsilyl Si<br />
DEPBT<br />
3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-<br />
4(3H)-one<br />
EtO<br />
OEt<br />
O<br />
P<br />
O<br />
O<br />
N<br />
N<br />
N<br />
DET<br />
diethyl tartrate<br />
O<br />
O<br />
HO<br />
OH<br />
(R)<br />
(R)<br />
O<br />
O<br />
DHP<br />
3,4-dihydro-2H-pyran<br />
O<br />
OMe<br />
DHQ<br />
dihydroquinine<br />
H<br />
OH<br />
N<br />
N<br />
H<br />
(DHQ) 2 PHAL<br />
bis(dihydroquinino)phthalazine<br />
MeO<br />
Et<br />
H<br />
N<br />
H<br />
O<br />
N<br />
N<br />
H<br />
O<br />
N<br />
H<br />
Et<br />
OMe<br />
N<br />
N<br />
OMe<br />
DHQD<br />
dihydroquinidine<br />
H<br />
N<br />
N<br />
H OH<br />
(DHQD) 2 PHAL<br />
bis(dihydroquinidino)phthalazine<br />
MeO<br />
H<br />
N<br />
H<br />
O<br />
Et<br />
N<br />
Et<br />
N<br />
H<br />
O<br />
N<br />
H<br />
OMe<br />
N<br />
N<br />
O<br />
N<br />
DIAD diisopropyl azodicarboxylate<br />
O N<br />
O<br />
O<br />
O<br />
DIB<br />
(BAIB or PIDA)<br />
(diacetoxyiodo)benzene<br />
O<br />
I<br />
O<br />
O<br />
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Abbreviation Chemical Name Chemical Structure<br />
DIBAL (DIBAH)<br />
DIBAL-H<br />
diisobutylaluminum hydride<br />
H<br />
Al<br />
DIC<br />
diisopropyl carbodiimide<br />
N<br />
C<br />
N<br />
O<br />
(R)<br />
PPh 2<br />
diop<br />
4,5-bis-[(diphenylphosphanyl)methyl]-2,2-dimethyl-<br />
[1,3]dioxolane<br />
O (R)<br />
PPh 2<br />
O<br />
DIPAMP 1,2-bis(o-anisylphenylphosphino)ethane P<br />
P<br />
O<br />
DIPEA<br />
(Hünig's base)<br />
diisopropylethylamine<br />
N<br />
DIPT<br />
diisopropyl tartrate<br />
O<br />
O<br />
HO<br />
OH<br />
(R) (R)<br />
O<br />
O<br />
O<br />
DLP<br />
dilauroyl peroxide<br />
C 10 H 21<br />
O<br />
O C 10 H 21<br />
O<br />
O<br />
DMA (DMAC)<br />
N,N-dimethylacetamide<br />
N<br />
DMAD<br />
dimethyl acetylene dicarboxylate<br />
O<br />
O<br />
O<br />
O<br />
DMAP N,N-4-dimethylaminopyridine N N<br />
DMB<br />
m-dimethoxybenzene<br />
O<br />
O<br />
DMDO dimethyl dioxirane O<br />
O<br />
O<br />
DME 1,2-dimethoxyethane O<br />
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Abbreviation Chemical Name Chemical Structure<br />
DMF<br />
N,N-dimethylformamide<br />
O<br />
H<br />
N<br />
O<br />
DMI 1,3-dimethylimidazolidin-2-one N N<br />
O<br />
DMP<br />
Dess-Martin periodinane<br />
AcO<br />
O<br />
I<br />
OAc<br />
OAc<br />
DMPS<br />
dimethylphenylsilyl<br />
Si<br />
DMPU<br />
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone<br />
(N,N-dimethyl propylene urea)<br />
N<br />
N<br />
O<br />
DMTSF dimethyl(methylthio)sulfonium tetrafluoroborate Me S S Me<br />
Me<br />
BF 4<br />
DMS dimethylsulfide S<br />
DMSO<br />
dimethylsulfoxide<br />
O<br />
S<br />
DMT<br />
4,4’-dimethoxytrityl<br />
O<br />
O<br />
O<br />
DMTMM<br />
4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-<br />
methylmorpholinium chloride<br />
O<br />
N<br />
N<br />
N<br />
N<br />
O<br />
Cl<br />
DMTr<br />
4,4’-dimethyltrityl<br />
DMTST<br />
(dimethylthio)methylsulfonium<br />
trifluoromethanesulfonate<br />
S<br />
S<br />
S<br />
O<br />
O<br />
S<br />
O<br />
F<br />
F<br />
F<br />
DNA deoxyribonucleic acid NA<br />
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Abbreviation Chemical Name Chemical Structure<br />
DPA (DIPA)<br />
diisopropylamine<br />
N<br />
H<br />
DPBP 2,2'-bis(diphenylphosphino)biphenyl<br />
(S)<br />
Ph 2 P PPh 2<br />
O<br />
O<br />
DPDC diisopropyl peroxydicarbonate<br />
O O<br />
O<br />
O<br />
N -<br />
N +<br />
DPDM<br />
diphenyl diazomethane<br />
DPEDA<br />
1,2-diamino-1,2-diphenylethane<br />
H 2 N NH 2<br />
(R) (R)<br />
Ph<br />
DPIBF diphenylisobenzofuran<br />
O<br />
Ph<br />
DPPA<br />
diphenylphosphoryl azide (diphenylphosphorazidate)<br />
O O<br />
P<br />
O<br />
N N + N -<br />
Dppb (ddpb) 1,4-bis(diphenylphosphino)butane Ph 2 P<br />
PPh 2<br />
dppe<br />
1,2-bis(diphenylphosphino)ethane<br />
Ph 2 P<br />
PPh 2<br />
dppf 1,1'-bis(diphenylphosphino)ferrocene Fe<br />
PPh 2<br />
PPh 2<br />
dppm<br />
bis(diphenylphosphino)methane<br />
Ph 2 P PPh 2<br />
dppp<br />
1,3-bis(diphenylphosphino)propane<br />
Ph 2 P PPh 2<br />
DPS<br />
(also TBDPS or<br />
BPS)<br />
t-butyldiphenylsilyl<br />
Si<br />
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Abbreviation Chemical Name Chemical Structure<br />
DPTC<br />
O,O’-di(2’-pyridyl)thiocarbonate<br />
N<br />
O<br />
S<br />
O<br />
N<br />
dr diastereomeric ratio NA<br />
O<br />
DTBAD (DBAD) di-tert-butyl azodicarboxylate N<br />
O N<br />
O<br />
O<br />
DTBB<br />
4,4’-di-tert-butylbiphenyl<br />
DTBP<br />
2,6-di-tert-butylpyridine<br />
N<br />
DTBMP<br />
2,6-di-tert-butyl-4-methylpyridine<br />
N<br />
DTE 1,4-dithioerythritol SH<br />
OH<br />
SH OH<br />
DVS<br />
1,3-divinyl-1,1,3,3-tetramethyldisiloxane<br />
Me Me<br />
O<br />
Si Si<br />
Me Me<br />
E +<br />
electrophile (denotes any electrophile in general)<br />
NA<br />
E2 bimolecular elimination NA<br />
ED effective dosage NA<br />
EDA<br />
ethyl diazoacetate<br />
O<br />
O<br />
N + N-<br />
EDDA<br />
ethylenediamine diacetate<br />
H 3 N<br />
OAc<br />
OAc<br />
NH 3<br />
EDC (EDAC)<br />
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide<br />
(ethyldimethylaminopropylcarbodiimide)<br />
N<br />
C<br />
N<br />
N<br />
EDCI<br />
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide<br />
hydrochloride<br />
N C N NH Cl<br />
PO 3 H 2<br />
EDCP<br />
2,3-bis-phosphonopentanedioic acid<br />
(ethylene dicarboxylic 2,3-diphosphonic acid)<br />
HOOC<br />
PO 3 H 2<br />
COOH<br />
EDG electron-donating group NA<br />
EDTA<br />
ethylenediamine tetraacetic acid<br />
HOOC<br />
HOOC<br />
N<br />
N<br />
COOH<br />
COOH<br />
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Abbreviation Chemical Name Chemical Structure<br />
ee enantiomeric excess NA<br />
EE<br />
ethoxyethyl<br />
O<br />
E i intramolecular syn elimination NA<br />
en<br />
ethylenediamine<br />
H 2 N<br />
NH 2<br />
EOM ethoxymethyl O<br />
ESR electron spin resonance (spectroscopy) NA<br />
Et<br />
ethyl<br />
ETSA<br />
ethyl trimethylsilylacetate<br />
O<br />
O<br />
Si<br />
EVE ethyl vinyl ether O<br />
EWG electron-withdrawing group NA<br />
Fc ferrocenyl Fe<br />
FDP<br />
fructose-1,6-diphosphate<br />
H 2 O 3 POH 2 C<br />
H<br />
H<br />
HO<br />
O<br />
HO<br />
H<br />
OH<br />
CH 2 OPO 3 H 2<br />
F<br />
FDPP<br />
pentafluorophenyl diphenylphosphinate<br />
F<br />
F<br />
Ph<br />
O<br />
P O F<br />
Ph<br />
F<br />
Fl<br />
fluorenyl<br />
FMO frontier molecular orbital (theory) NA<br />
O<br />
Fmoc<br />
9-fluorenylmethoxycarbonyl<br />
O<br />
fod<br />
6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-<br />
octanedione<br />
F<br />
F<br />
F F O<br />
F F F<br />
O<br />
fp flash point NA<br />
FSM Mesoporous silica NA<br />
FTT 1-fluoro-2,4,6-trimethylpyridinium triflate N F S<br />
O<br />
O<br />
O<br />
F<br />
F<br />
F<br />
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Abbreviation Chemical Name Chemical Structure<br />
FVP flash vacuum pyrolysis NA<br />
GEBC gel entrapped base catalyst NA<br />
h hours (length of reaction time) NA<br />
hν irradiation with light NA<br />
HATU<br />
O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-<br />
tetramethyluronium hexafluorophosphate<br />
N<br />
PF 6<br />
O + N<br />
N N<br />
N<br />
N<br />
Het heterocycle NA<br />
O<br />
O<br />
hfacac hexafluoroacetylacetone F 3 C<br />
CF 3<br />
F<br />
F F<br />
F<br />
HFIP<br />
1,1,1,3,3,3-hexafluoro-2-propanol<br />
(hexafluoroisopropanol)<br />
F<br />
OH<br />
F<br />
HO<br />
HGK<br />
4-hydroxy-2-ketoglutarate<br />
O<br />
O<br />
O<br />
O<br />
O<br />
Hgmm millimeter of mercury (760 Hgmm = 1 atm = 760 Torr) NA<br />
HLE horse liver esterase NA<br />
Hmb<br />
2-hydroxy-4-methoxybenzyl<br />
O<br />
OH<br />
HMDS<br />
1,1,1,3,3,3-hexamethyldisilazane<br />
Si<br />
H<br />
N<br />
Si<br />
N<br />
HMPA<br />
hexamethylphosphoric acid triamide<br />
(hexamethylphosphoramide)<br />
N<br />
P<br />
O<br />
N<br />
N<br />
HMPT hexamethylphosphorous triamide N P<br />
N<br />
N<br />
HOAt 1-hydroxy-7-azabenzotriazole<br />
N<br />
N N<br />
OH<br />
N<br />
HOBt (HOBT) 1-hydroxybenzotriazole<br />
N<br />
N<br />
HOMO highest occupied molecular orbital NA<br />
OH<br />
HOSu<br />
N-hydroxysuccinimide<br />
O<br />
OH<br />
N<br />
O<br />
HPLC high-pressure liquid chromatography NA<br />
HWE Horner-Wadsworth-Emmons NA<br />
i iso NA<br />
xxx
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
IBA 2-iodosobenzoic acid O<br />
O<br />
I<br />
HO<br />
O<br />
IBX<br />
o-iodoxybenzoic acid<br />
HO<br />
O<br />
I<br />
O<br />
IDCP<br />
bis(2,4,6-collidine)iodonium perchlorate<br />
N I + N ClO 4 -<br />
Imid (Im)<br />
imidazole<br />
HN<br />
N<br />
INOC intramolecular nitrile oxide cycloaddition NA<br />
IPA isopropyl alcohol HO<br />
Ipc<br />
isopinocamphenyl<br />
H<br />
IR infrared spectroscopy NA<br />
K-10 a type of Montmorillonite clay NA<br />
KDA<br />
potassium diisopropylamide<br />
N<br />
K<br />
K<br />
KHMDS<br />
potassium bis(trimethylsilyl)amide<br />
N<br />
Si Si<br />
KSF a type of Montmorillonite clay NA<br />
L ligand NA<br />
L.R.<br />
Lawesson’s reagent (2,4-bis-(4-methoxyphenyl)-<br />
[1,3,2,4]dithiadiphosphetane 2,4-dithion)<br />
MeO<br />
S<br />
P<br />
S<br />
S<br />
P<br />
S<br />
OMe<br />
LA Lewis acid NA<br />
LAB lithium amidotrihydroborate LiH 2 NBH 3<br />
LAH<br />
lithium aluminum hydride<br />
LiAlH 4<br />
LD 50<br />
dose that is lethal to 50% of the test subjects (cells,<br />
animals, humans etc.)<br />
NA<br />
LDA<br />
lithium diisopropylamide<br />
N<br />
Li<br />
LDBB lithium 4,4’-t-butylbiphenylide Li<br />
xxxi
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
LDE lithium diethylamide Li<br />
N<br />
LDPE<br />
lithium perchlorate-diethyl etherate<br />
LiClO 4 - Et 2 O<br />
LHMDS<br />
(LiHMDS)<br />
lithium bis(trimethylsilyl)amide<br />
Li<br />
N<br />
Si Si<br />
LICA<br />
lithium isopropylcyclohexylamide<br />
Li<br />
N<br />
BuLi - KOt-Bu<br />
LICKOR (super<br />
butyllithium-potassium tert-butoxide<br />
base)<br />
liq. liquid NA<br />
LiTMP<br />
(LTMP)<br />
lithium 2,2,6,6-tetramethylpiperidide<br />
N<br />
Li<br />
LPT<br />
lithium pyrrolidotrihydroborate<br />
(lithium pyrrolidide-borane)<br />
Li(CH 2 ) 4 NBH 3<br />
L-selectride<br />
lithium tri-sec-butylborohydride<br />
BH<br />
Li<br />
LTA<br />
lead tetraacetate<br />
Pb(OAc) 4<br />
LUMO lowest unoccupied molecular orbital NA<br />
lut<br />
2,6-lutidine<br />
N<br />
m meta NA<br />
MA<br />
maleic anhydride<br />
O<br />
O<br />
O<br />
MAD<br />
methyl aluminum bis(2,6-di-t-butyl-4-<br />
methylphenoxide)<br />
O<br />
AlMe<br />
2<br />
MAT methyl aluminum bis(2,4,6-tri-t-butylphenoxide) O AlMe<br />
2<br />
xxxii
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
MBT<br />
2-mercaptobenzothiazole<br />
HS<br />
S<br />
N<br />
COOOH<br />
m-CPBA<br />
meta chloroperbenzoic acid<br />
Cl<br />
Me<br />
methyl<br />
CH 3<br />
MEM (2-methoxyethoxy)methyl<br />
O<br />
O<br />
MEPY<br />
methyl 2-pyrrolidone-5(S)-carboxylate<br />
O<br />
O<br />
H<br />
N<br />
O<br />
Mes<br />
mesityl<br />
HO<br />
mesal<br />
N-methylsalicylaldimine<br />
N<br />
MIC methyl isocyanate O C N<br />
MMPP<br />
(MMPT)<br />
magnesium monoperoxyphthalate<br />
Mg 2+<br />
O<br />
O<br />
O<br />
O<br />
O<br />
MOM<br />
methoxymethyl<br />
oxodiperoxomolybdenum(pyridine)-<br />
NA<br />
MoOPH<br />
(hexamethylphosphoric triamide)<br />
mp melting point NA<br />
MPa<br />
megapascal = 10 6 Pa = 10 atm (pressure)<br />
O<br />
MPD<br />
(NMP)<br />
N-methyl-2-pyrrolidinone<br />
N<br />
O<br />
O<br />
MPM methoxy(phenylthio)methyl S<br />
MPM<br />
(PMB)<br />
p-methoxybenzyl<br />
O<br />
xxxiii
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
Cl<br />
MPPC<br />
N-methyl piperidinium chlorochromate<br />
O<br />
Cr<br />
O<br />
O<br />
NH<br />
O<br />
Ms<br />
mesyl (methanesulfonyl)<br />
S<br />
O<br />
CH 3<br />
MS mass spectrometry NA<br />
MS molecular sieves NA<br />
O<br />
MSA<br />
methanesulfonic acid<br />
HO<br />
S<br />
O<br />
CH 3<br />
MSH<br />
o-mesitylenesulfonyl hydroxylamine<br />
HO<br />
H O<br />
N<br />
S<br />
O<br />
MSTFA<br />
N-methyl-N-(trimethylsilyl) trifluoroacetamide<br />
F<br />
F<br />
F<br />
O<br />
Si<br />
N<br />
MTAD N-methyltriazolinedione O<br />
N<br />
O<br />
N N<br />
MTEE<br />
(MTBE)<br />
methyl t-butyl ether<br />
O<br />
MTM<br />
MTO<br />
methylthiomethyl<br />
methyltrioxorhenium<br />
S<br />
O<br />
O Re CH 3<br />
O<br />
Me Me<br />
O<br />
Mtr (4-methoxy-2,3,6-trimethylphenyl)sulfonyl<br />
S<br />
OMe<br />
O<br />
Me<br />
MVK<br />
methyl vinyl ketone<br />
O<br />
mw microwave NA<br />
n normal (e.g. unbranched alkyl chain) NA<br />
H<br />
H<br />
O<br />
NH 2<br />
O<br />
O<br />
N<br />
NADPH<br />
nicotinamide adenine dinucleotide phosphate<br />
OH OH<br />
N<br />
NH 2<br />
N<br />
O<br />
P O<br />
OH<br />
O<br />
P O<br />
OH<br />
N N<br />
O<br />
O<br />
OH O P OH<br />
OH<br />
xxxiv
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
NaHMDS<br />
sodium bis(trimethylsilyl)amide<br />
Na<br />
N<br />
Si Si<br />
Naph<br />
(Np)<br />
naphthyl<br />
O<br />
NBA<br />
N-bromoacetamide<br />
Br<br />
N<br />
H<br />
NBD<br />
(nbd)<br />
norbornadiene<br />
O<br />
NBS<br />
N-bromosuccinimide<br />
N<br />
Br<br />
O<br />
O<br />
NCS<br />
N-chlorosuccinimide<br />
N<br />
Cl<br />
O<br />
N f nonafluorobutanesulfonyl<br />
S<br />
O<br />
O<br />
F<br />
F<br />
F<br />
F<br />
F<br />
F<br />
F<br />
F<br />
F<br />
O<br />
NHPI<br />
N-hydroxyphthalimide<br />
N<br />
OH<br />
O<br />
NIS N-iodosuccinimide O<br />
N<br />
O<br />
I<br />
NMM N-methylmorpholine N O<br />
NMO<br />
N-methylmorpholine oxide<br />
O<br />
N<br />
O<br />
O<br />
NMP N-methyl-2-pyrrolidinone N<br />
NMR nuclear magnetic resonance NA<br />
NORPHOS<br />
bis(diphenylphosphino)bicyclo[2.2.1]-hept-5-ene<br />
Ph 2 P PPh 2<br />
Nos 4-nitrobenzenesulfonyl<br />
S<br />
O<br />
O<br />
N<br />
O<br />
O<br />
xxxv
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
O<br />
NPM<br />
N-phenylmaleimide<br />
N<br />
O<br />
NR no reaction NA<br />
Ns<br />
2-nitrobenzenesulfonyl<br />
O<br />
O<br />
S<br />
O<br />
O<br />
N<br />
NSAID non steroidal anti-inflammatory drug NA<br />
Nuc nucleophile (general) NA<br />
o ortho NA<br />
Oxone<br />
potassium peroxymonosulfate<br />
p para NA<br />
KHSO 5<br />
PAP<br />
2,8,9-trialkyl-2,5,8,9-tetraaza-<br />
1-phospha-bicyclo[3.3.3]undecane<br />
R<br />
N<br />
P<br />
N<br />
N<br />
R<br />
R<br />
N<br />
PBP<br />
pyridinium bromide perbromide<br />
N<br />
H<br />
Br 3<br />
PCC<br />
pyridinium chlorochromate<br />
N<br />
H<br />
O<br />
O Cr<br />
O<br />
Cl<br />
PDC<br />
pyridinium dichromate<br />
N<br />
H<br />
O<br />
Cr<br />
O O<br />
O<br />
O<br />
Cr O<br />
O<br />
N<br />
H<br />
PEG polyethylene glycol NA<br />
Ph<br />
Pf<br />
9-phenylfluorenyl<br />
pfb<br />
perfluorobutyrate<br />
F<br />
F<br />
F<br />
F<br />
F<br />
F<br />
O<br />
F<br />
O<br />
Ph<br />
phenyl<br />
PHAL phthalazine N<br />
N<br />
phen<br />
9,10-phenanthroline<br />
N N<br />
xxxvi
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
Phth<br />
phthaloyl<br />
O<br />
C<br />
C<br />
O<br />
pic<br />
2-pyridinecarboxylate<br />
O<br />
O<br />
N<br />
O<br />
PIDA<br />
(BAIB or DIB)<br />
phenyliodonium diacetate<br />
O<br />
I<br />
O<br />
O<br />
PIFA<br />
phenyliodonium bis(trifluoroacetate)<br />
F 3 C<br />
O<br />
O<br />
I<br />
O<br />
O<br />
CF 3<br />
Piv pivaloyl O<br />
PLE pig liver esterase NA<br />
PMB<br />
(MPM)<br />
p-methoxybenzyl<br />
O<br />
PMP 4-methoxyphenyl O<br />
PMP<br />
1,2,2,6,6-pentamethylpiperidine<br />
Me<br />
Me<br />
N<br />
Me<br />
Me<br />
Me<br />
PNB<br />
p-nitrobenzyl<br />
O<br />
N<br />
O<br />
PNZ<br />
p-nitrobenzyloxycarbonyl<br />
O<br />
N<br />
O<br />
O<br />
O<br />
PPA<br />
polyphosphoric acid<br />
NA<br />
PPI<br />
2-phenyl-2-(2-pyridyl)-2H-imidazole<br />
N<br />
N<br />
N<br />
PPL pig pancreatic lipase NA<br />
PPO 4-(3-phenylpropyl)pyridine-N-oxide O N Ph<br />
PPSE polyphosphoric acid trimethylsilyl ester NA<br />
xxxvii
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
O<br />
PPTS<br />
pyridinium p-toluenesulfonate<br />
S<br />
O<br />
O<br />
N<br />
H<br />
Pr<br />
propyl<br />
psi pounds per square inch NA<br />
PT 1-phenyl-1H-tetrazol-yl N<br />
P.T. proton transfer NA<br />
Ph<br />
N<br />
N<br />
N<br />
PTAB phenyltrimethylammonium perbromide N Br 3<br />
PTC Phase transfer catalyst NA<br />
PTMSE<br />
(2-phenyl-2-trimethylsilyl)ethyl<br />
Si<br />
PTSA<br />
(or TsOH) p-toluenesulfonic acid HO 3 S<br />
CH 3<br />
PVP poly(4-vinylpyridine) NA<br />
Py<br />
pyridine<br />
(pyr)<br />
N<br />
r.t. room temperature NA<br />
rac racemic NA<br />
NH 2<br />
RAMP<br />
(R)-1-amino-2-(methoxymethyl)pyrrolidine<br />
N<br />
(R)<br />
O<br />
RaNi Raney nickel NA<br />
RB Rose Bengal See Rose bengal<br />
RCAM ring-closing alkyne metathesis NA<br />
RCM ring-closing metathesis NA<br />
Rds (or RDS) rate-determining step NA<br />
Red-Al<br />
sodium bis(2-methoxyethoxy) aluminum hydride<br />
O<br />
O<br />
O<br />
Al H<br />
H<br />
O<br />
Na<br />
Rham<br />
rhamnosyl<br />
H<br />
O Me<br />
O<br />
O<br />
O<br />
H<br />
H<br />
R f perfluoroalkyl group<br />
C n F 2n+1<br />
R f retention factor in chromatography NA<br />
ROM ring-opening metathesis NA<br />
ROMP ring-opening metathesis polymerization NA<br />
xxxviii
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
Rose Bengal<br />
(RB)<br />
2,4,5,7-tetraiodo-3',4',5',6'-tetrachlorofluorescein<br />
disodium salt<br />
(a photosensitizer)<br />
O<br />
I<br />
I<br />
Cl<br />
O<br />
I<br />
O<br />
I<br />
COO<br />
2 Na<br />
Cl<br />
Cl<br />
Cl<br />
s seconds (length of reaction time) NA<br />
PPh 2<br />
S,S,-chiraphos (S,S)-2,3-bis(diphenylphosphino)butane<br />
(S)<br />
(S)<br />
PPh 2<br />
Salen<br />
N,N’-ethylenebis(salicylideneiminato)<br />
bis(salicylidene)ethylenediamine<br />
N<br />
OH<br />
N<br />
HO<br />
salophen o-phenylenebis(salicylideneiminato) N N<br />
OH<br />
HO<br />
SAMP (S)-1-amino-2-(methoxymethyl)pyrrolidine<br />
N<br />
NH 2<br />
O<br />
SC CO 2 supercritical carbon-dioxide NA<br />
SDS<br />
sodium dodecylsulfate<br />
O<br />
O Na<br />
S O<br />
O<br />
sec secondary NA<br />
SEM 2-(trimethylsilyl)ethoxymethyl<br />
O<br />
Si<br />
SES 2-[(trimethylsilyl)ethyl]sulfonyl<br />
Si<br />
O<br />
S<br />
O<br />
SET single electron transfer NA<br />
Sia<br />
1,2-dimethylpropyl (secondary isoamyl)<br />
SPB sodium perborate Na BO 3<br />
xxxix
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
TADDOL<br />
2,2-dimethyl-α,α,α 1 , α 1 -tetraaryl-1,3-dioxolane-4,5-<br />
dimethanol<br />
O<br />
O<br />
OH<br />
H Ar<br />
(R)<br />
(R)<br />
Ar<br />
Ar<br />
H Ar<br />
OH<br />
NEt 2<br />
TASF<br />
tris(diethylamino)sulfonium difluorotrimethylsilicate<br />
Et 2 N<br />
S<br />
NEt 2<br />
SiMe 3 F 2<br />
TBAB<br />
tetra-n-butylammonium bromide<br />
N<br />
Br<br />
TBAF tetra-n-butylammonium fluoride Bu 4 N F<br />
TBAI tetra-n-butylammonium iodide Bu 4 N I<br />
Br<br />
TBCO<br />
tetrabromocyclohexadienone<br />
Br<br />
Br<br />
Br<br />
O<br />
TBDMS<br />
(TBS)<br />
t-butyldimethylsilyl<br />
Si<br />
TBDPS<br />
(BPS)<br />
t-butyldiphenylsilyl<br />
Si<br />
O<br />
TBH tert-butyl hypochlorite Cl<br />
TBHP tert-butyl hydroperoxide<br />
O<br />
OH<br />
TBP<br />
tributylphosphine<br />
P<br />
TBT 1-tert-butyl-1H-tetrazol-5-yl N<br />
t-Bu<br />
N<br />
N<br />
N<br />
TBTH<br />
tributyltin hydride<br />
H<br />
Sn<br />
TBTSP<br />
t-butyl trimethylsilyl peroxide<br />
O<br />
Si O<br />
xl
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
TCCA trichloroisocyanuric acid<br />
Cl N<br />
O<br />
O<br />
Cl<br />
N<br />
N<br />
Cl<br />
O<br />
S<br />
TCDI<br />
thiocarbonyl diimidazole<br />
N<br />
N<br />
N<br />
N<br />
N<br />
N<br />
TCNE<br />
tetracyanoethylene<br />
N<br />
N<br />
TCNQ<br />
7,7,8,8-tetracyano-para-quinodimethane<br />
NC<br />
NC<br />
CN<br />
CN<br />
TDS<br />
dimethyl thexylsilyl<br />
Si<br />
TEA triethylamine N<br />
TEBACl benzyl trimethylammonium chloride N<br />
Cl<br />
TEMPO<br />
2,2,6,6-tetramethyl-1-piperidinyloxy free radical<br />
N<br />
O•<br />
Teoc<br />
2-(trimethylsilyl)ethoxycarbonyl<br />
O<br />
O<br />
Si<br />
TEP<br />
triethylphosphite<br />
O<br />
P<br />
O<br />
O<br />
TES triethylsilyl Si<br />
Tf<br />
trifluoromethanesulfonyl<br />
F<br />
F<br />
F<br />
O<br />
S<br />
O<br />
TFA<br />
trifluoroacetic acid<br />
F<br />
F<br />
F<br />
OH<br />
O<br />
Tfa<br />
trifluoroacetamide<br />
F<br />
F<br />
F<br />
NH 2<br />
O<br />
xli
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
TFAA<br />
trifluoroacetic anhydride<br />
F<br />
F<br />
F<br />
O<br />
O<br />
O<br />
F<br />
F<br />
F<br />
TFE<br />
2,2,2-trifluoroethanol<br />
F<br />
F<br />
F<br />
OH<br />
TFMSA<br />
trifluoromethanesulfonic acid<br />
(triflic acid)<br />
F<br />
F<br />
F<br />
O<br />
S<br />
O<br />
OH<br />
TFP<br />
tris(2-furyl)phosphine<br />
O<br />
P<br />
O<br />
O<br />
Th<br />
2-thienyl<br />
S<br />
thexyl<br />
1,1,2-trimethylpropyl<br />
THF<br />
tetrahydrofuran<br />
O<br />
THP 2-tetrahydropyranyl O<br />
TIPB<br />
1,3,5-triisopropylbenzene<br />
TIPS triisopropylsilyl Si<br />
TMAO (TMANO) trimethylamine N-oxide<br />
N + O -<br />
TMEDA<br />
N,N,N',N'-tetramethylethylenediamine<br />
N<br />
N<br />
TMG<br />
1,1,3,3-tetramethylguanidine<br />
N<br />
NH<br />
N<br />
TMGA<br />
tetramethylguanidinium azide<br />
N<br />
N<br />
NH 2<br />
N 3<br />
xlii
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
O<br />
Tmob<br />
2,4,6-trimethoxybenzyl<br />
O<br />
O<br />
TMP<br />
2,2,6,6-tetramethylpiperidine<br />
N<br />
H<br />
TMS trimethylsilyl<br />
Si<br />
TMSA trimethylsilyl azide Si<br />
N<br />
N<br />
+<br />
N -<br />
TMSEE<br />
(trimethylsilyl)ethynyl ether<br />
Si<br />
O<br />
Si<br />
TMU<br />
tetramethylurea<br />
N<br />
O<br />
N<br />
TNM<br />
tetranitromethane<br />
-<br />
O<br />
-<br />
O<br />
N +<br />
O<br />
-<br />
O<br />
N O + O<br />
N +<br />
N + O -<br />
O<br />
Tol<br />
p-tolyl<br />
tolbinap<br />
2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl<br />
P<br />
P<br />
2<br />
2<br />
TPAP<br />
tetra-n-propylammonium perruthenate<br />
N<br />
O<br />
O Ru O<br />
O<br />
TPP<br />
triphenylphosphine<br />
P<br />
Ph<br />
TPP<br />
5,10,15,20-tetraphenylporphyrin<br />
Ph<br />
NH<br />
N<br />
N<br />
HN<br />
Ph<br />
Ph<br />
xliii
TABLE <strong>OF</strong> CONTENTS<br />
SEARCH TEXT<br />
Abbreviation Chemical Name Chemical Structure<br />
TPS triphenylsilyl Si<br />
Tr trityl (triphenylmethyl) C<br />
O<br />
Trisyl 2,4,6-triisopropylbenzenesulfonyl S<br />
O<br />
Troc<br />
2,2,2-trichloroethoxycarbonyl<br />
O<br />
O<br />
Cl<br />
Cl<br />
Cl<br />
TS transition state (or transition structure) NA<br />
Ts (Tos)<br />
p-toluenesulfonyl<br />
O<br />
S<br />
O<br />
TSE (TMSE) 2-(trimethylsilyl)ethyl Si<br />
TTBP<br />
2,4,5-tri-tert-butylpyrimidine<br />
N<br />
N<br />
TTMSS tris(trimethylsilyl)silane Si SiH<br />
Si<br />
Si<br />
TTN<br />
thallium(III)-trinitrate<br />
Tl(NO 3 ) 3<br />
UHP<br />
urea-hydrogen peroxide complex<br />
H 2<br />
N<br />
O<br />
NH 2<br />
H 2 O 2<br />
Vitride<br />
(Red-Al)<br />
sodium bis(2-methoxyethoxy)aluminum hydride<br />
O<br />
O<br />
O<br />
Al H<br />
H<br />
Na<br />
O<br />
wk weeks (length of reaction time) NA<br />
Z (Cbz)<br />
benzyloxycarbonyl<br />
O<br />
O<br />
xliv