Abbreviations update: 2008/04/03, K. Oisaki A AAA asymmetric allylic alkylation Ac acetyl Me O O acac O acetylacetonate Me Ad 1-adamantyl AD asymmetric dihydroxylation Adoc 1-adamantyloxycarbonyl ADMET AE acyclic diene polymerization asymmetric epoxidation Me O O CN AIBN N 2,2’-azobisisobutyronitrile N CN O Alloc allyloxycarobonyl O Alpine Borane B-isopinocamphenyl-9-borabicyclo [3.3.1] nonane Am amyl amu anhyd. aq. atomic mass unit Anhydrous Aqueous or water solution B O AQN anthraquinone O Ar atm au aryl or argon atmosphere atomic unit B H B 9-BBN 9-borabicyclo[3.3.1]nonane BHT 2,6-di-t-butyl-p-cresol BINOL 1,1’-bi-2,2’-naphthol HB OH HO HO bipy or bpy 2,2’-bipyridyl bmim 1-butyl-3-methylimidazolium cation BMS borane-dimethyl sulfide complex Bn benzyl Boc t-butoxycarbonyl N N N N O O BOM benzyloxymethyl BOP benzortriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate BOP-Cl bis(2-oxo-3-oxazolidiny)phosphinic chloride O N N N Me2N O Me2N P PF6 Me2N O O O O N P O N Cl b. p. or bp boiling point or B2Pin2 bis(pinacolato)diboron (Bpin)2 O O B B O O O Bpoc 1-methyl-1-(4-biphenyl)ethoxycarbonyl BQ benzoquinone O O O Bredereck’s reagent Me2N t-butoxybis(dimethylamino)methane O NMe2 Me2N BroP Bromotris(dimethylamino)phosphonium hexafluorophosphate Br Me2 N P Me2 N PF6 O O Bs S p-bromobenzenesulfonyl (brosyl) Br BSA BSTFA N,O-bis(trimethylsilyl)acetamide N,O-bis(trimethylsilyl)trifluoroacetamide O Me3Si N O Me3 Si N SiMe3 Me SiMe3 CF3 N Bt 1- or 2-benzotriazol N N BTA benzyltrimethylammonium cation i Bu iso-butyl sec-Bu secondary-butyl N n t Bu normal-butyl Bu tertiary-butyl O Burgess’ reagent Methoxycarbonylsulfamoyl)triethylammonium Hydroxide, Inner Salt Bz benzoyl O S Et3 N O N OMe O CAMCR CAN cat. C catalytic asymmetric multicomponent reaction ceric ammonium nitrate Catalyst or catalytic amount of (NH4)2[Ce(NO3)6] Ar CBS catalyst N Ar O B R Ph Cbz or Z O benzyloxycarbonyl O CD circular dichromism or cyclodextrin O CDI carbonyl diimidazole CHD 1,3- or 1,4-cyclohexadiene chroramine-T p-toluenesulfonchloramide sodium salt N N N N or Ts N Na Cl CI-MS chemical ionization mass spectrometry Cl CIP 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate N N PF6 O CMHP cumene hydroperoxide CMMP cyanomethylenetrimethyl phosphorane COD 1,5-cyclooctadiene Collins’ reagent Collman’s reagent NC OH P dipyridine chromium(VI) oxide CrO3(Py)2 disodium tetracarbonylferrate Na2Fe(CO)4 Cl Comin’s reagent 2-[N,N-bis(trifluoromethylsulfonyl)amino]-5-chloropyridine conc. Concentrated N NTf2 conv. Conversion Corey lactone (3aR,4S,5R,6aS)-(-)-5-(benzoyloxy)-hexahydro-4(-hydroxymethyl)-2 H-cyclopenta[b]furan-2-one O O BzO OH COSY correlation spectroscopy COT cyclooctatetraene Cp cyclopentadienyl Cp* 1,2,3,4,5-pentamethyl cyclopentadienyl CPME cyclopentylmethyl ether O Crabtree’s catalyst (SP-4)tris(cyclohexyl)phosphane [(1-2-η:5-6-η)-cycloocta-1,5-diene] [Ir(cod)(py)(PCy3)]P pyridineiridium hexafluoridophosphate F6 CSA (1S)-(+)-10-comphorsulfonic acid CSI CSI-MS CT chlorosulfonyl isocyanate cold spray ionization mass spectrometry charge transfer c cyclohexyl Hex or Cy SO3H O ClSO2NCO D d ∆ days heat DABCO 1,4-diazabycyclo[2.2.2]octane N N DAIB 3-exo-dimethylaminoisoborneol DAST diethylaminosulfer trifluoride NMe2 OH Et2N S F F F O dba dibenzylideneacetone Ph DBN Ph N 1,5-diazabicyclo[4.3.0]non-5-ene N DBU N 1,8-diazabicyclo[5.4.0]undec-7-ene N DCB Cl 1,2-dichlorobenzene Cl DCC dicyclohexylarbodiimide DCE DCM 1,2-dichloroethane dichloromethane DCU N,N’-dicyclohexylurea N N C ClCH2CH2Cl CH2Cl2 O N H N H O NC DDQ Cl 2,3-dichloro-5,6-dicyano-1,4-benzoquinone NC Cl O DEAD deg DEIPS diethyl azodicarboxylate degree diethylisopropylsilyl DET EtO2C N N CO2 Et Et2iiiPrSiEtO2 C OH EtO2 C OH diethyl tartrate DHP 3,4-dihydro-2H-pyran DIAD diisopropyl azodicarboxylate i O PrO2 C N N CO2 iPr Me Diazald p-toluenesulphonylmethylnitrosamide DIBAL DIBAH or diisopropyl carbodiimide dien diethylenetriamine diglyme diethylene glycol dimethyl ether DIPEA DIPA diisopropylethylamine diisopropylamine Al H N C N H NH2 N NH2 O OMe i Pr2NEt i Pr2NH i PrO2C OMe OH diisopropyl tartrate iPrO DMA N diisobutylaluminium hydride DIC DIPT O N Ts N,N-dimethylacetamide OH 2C N O MeO DMB dimethoxybenzyl OMe DMAD dimethyl acetylenedicarboxylate MeO 2C DMAP 4-(dimethylamino)pyridine Me2N CO 2Me N DMDO dimethyldioxirane DME 1,2-dimethoxyethane DMF N,N-dimethylformamide O O MeO OMe N H O DMG directed metalation group O DMI 1,3-dimethylimidazolidine-2-one N N AcO I DMP OAc OAc Dess-Martin periodinane O O O DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone DMS dimethylsulfide DMSO dimethylsulfoxide DMTr 4,4’-dimethoxytrityl N N Me2S S O NO2 DNPH 2,4-dinitrophenylhydrazine H N NH2 O2N NO2O DNs O S 2,4-dinitrobenzenesulfonyl O2N DoM directed ortho metalation Dpp diphenylphosphinyl Ph Ph Drierite anhydrous carcium sulfate DPPA diphenylphosphinyl azide DTBB 4,4’-di-t-butylbiphenyl DTBMP 2,6-di-t-butyl-4-methylpyridine O P CaSO4 O N3 P OPh OPh N DTBP 2,6-di-t-butylpyridine dr diastereomeric ratio N E E EDC EDCI entgegen or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride N C N NMe2 -HCl EDG electron donating group CO2H EDTA ethylenediamine tetraacetic acid HO2C N CO2H N HO2C EE 1-ethoxyethyl ee EI-MS enantiomeric excess electron impact mass spectrometry en ethylenediamine ENDOR EPR eq or equiv Eschenmoser reagent ESI-MS ESR Et ET EVE EWG EXAFS EXSY electron-nuclear double resonance electron paramagnetic resonance equivalent NN-dimethylmethyleneammonium idodide FAB-MS electrospray ionization mass spectrometry electron spin resonance ethyl electron transfer ethyl vinyl ether electron withdrawing group extended X-ray absorption fine structure exchange spectroscopy F fast atom bombardment mass spectrometry FAMSO formaldehyde dimethyldithioacetal S-oxide O NH2 H2N N I O Me S S Me O Fc ferrocenyl Fetizon’s reagent FMO frontier molecular orbital Fmoc 9-fluorenylmethoxylcarbonyl silver carbonate – celite Fe Ag2CO3 O O FG fp or f.p. FRET FT-IR FT-NMR FVP functional group flash point fluorescence resonance energy transfer Fourier transfer infrared spectroscopy Fourier transfere nuclear magnetic resonance flash vacuum pyrolysis G Garner’s aldehyde O O N-Boc-N,O-isopropylideneserinal N H Boc GC gas chromatography gem geminal GPC gel permeation chromatography st Grubbs’ 1 generation catalyst Cy3P Cl Ru Cl Cy3P Grubbs’ 2nd generation catalyst Ph Mes N N Mes Cl Ru Cl Cy3P Ph Cy3P Cl Ru Cl O Grubbs-Hove yda catalyst Mes N Cl N Mes Ru Cl O H h or hr Hantzsch ester hour EtO2C CO 2Et diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate N H N HATU O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate N N Me2N N O PF6 Me2N N HBTU O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate N N Me2 N O PF6 Me2N Het heterocycles hfa hexafluoroacetylacetonate HMBC H-detected multiple-bond heteronuclear multiple quantum coherenece HMDS 1,1,1,3,3,3-hexamethyldisilazane O O F3C Me3Si CF3 N SiMe3 H Me2N HMPA hexamethylphosphoramide HMPT hexamethylphosphorous triamide O Me2N P Me2N Me2 N Me N P 2 Me2 N hν irradiation with light N HOAt 1-hydroxy-7-azabenzotriazole N N HO N N HOBt N 1-hydroxybenzotriazole N HO HOHAHA HOMO homonuculear Hartmann-Hahn spectrum highest occupied molecular orbital O HOSu N-hydroxysuccinimide N OH O HPLC HSAB HTS Hunig’s base HWE reaction high performance liquid chromatography hard and soft acids and bases high throughput screening diisopropyethylamine i Pr2NEt Horner-Wadsworth-Emmons reaction I OH I IBX 2-iodoxybenzoic acid O O Imid or Im H N imidazole N INADEQUA TE INDOR INEPT internuclear double resonance insensitive nuclei enhanced by polarization transfer IPA isopropyl alcohol Ipc isopinocampheyl IUPAC IR International Union of Pure and Applied Chemistry infrared spectroscopy J K KDA potassium diisopropylamide KHMDS potassium hexamethyldisilazide K-Selectride potassium tri-s-butylborohydride incredible natural abundance double quantum transfere experiment OH N K Si N K Si K BH 3 L LA or L.A. LAH Lewis acid lithium aluminium hydride LiAlH4 Lawesson’s reagent LB or L.B. LD 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfi de Lewis base lethal dose LDA lithium diisopropylamide LDBB Lithium 4,4’-di-t-butylbiphenylide LHMDS lithium hexamethyldisilazide LICA lithium isopropylcyclohexylamide S MeO S P P S OMe S N Li Si Si N Li N Li liq. LTA Liquid lead tetraacetate LiTMP lithium 2,2,6,6-tetramethylpiperidide Pb(Oac)4 N Li LLB LaLi3tris(binaphtoxide) L-Selectride lithium tri-s-butylborohydride Li BH 3 LUMO lowest unoccupied molecular orbital M OR MAC masked acyl cyanide NC CN t Me MAD methyl aluminium bis(2,4,6-tri-t-butyl-4-methylphenoxide) Al O t MALDI Mander’s reagent MAO Matrin sulfurane Bu tBu Me O t Bu Bu matrix-assisted laser desorption ionization MeO CN methoxycarbonylcyanide O methylaluminoxane Ph CF3 F3C S F3 C Ph Ph CF 3 Ph Bis[α,α-bis(trifluoromethyl)benzenemethanolato]diphenylsulfur O O O O Mbs Me S p-methoxybenzenesulfonyl MeO O mCPBA m-chloroperbenzoic acid Me methyl Meldrum’s acid 2,2-dimethyl-1,3-dioxane-4,6-dione MEM 2-methoxyethoxymethyl Cl O O O Me O O O O OH Mes mesityl (2,4,6-trimethylphenyl) min minute O MMPP O O magnesium monoperoxyphtalate O Mg O MMTr p-methoxyphenyldiphenylmethyl NO2 O MNBA 2-methyl-6-nitrobenzoic anhydride MO MOM molecular orbital methoxymethyl O O O Me MeO MPM p-methoxybenzyl mp or m.p. melting point Ms methanesulfonyl (mesyl) MS molecular sieves O O S Me O O MSH S o-mesitylenesulfonyl hydroxylamine O NH2 O MSTFA N-methyl-N-(trimethylsilyl)trifluoroacetamide Me3 Si N CF3 Me MTBE MTM MTO MTPA-Cl methyl tert-butyl ether O Me methylthiomethyl methyltrioxorhenium S MeReO3 α-methoxy- α -trifluoromethyl-phenylacetyl chloride F3C Ph O Cl OMe O MVK methyl vinyl ketone M.W. µW molecular weight microwave N NaHMDS sodium hexamethyldisilazide Naph or Np naphthyl NBA N-bromoacetamide Si N Na Si O N H Br NO2 nbd norbornadiene O NBS N-bromosuccinimide N Br O O NCS N-chlorosuccinimide N Cl O O O Nf nonafluorobutanesulfonyl S C4F9 O NHPI N-hydroxyphthalimide N OH O NICS nucleus-independent chemical shift O NIS N-iodosuccinimide N I O NMM N-methylmorpholine NMO N-methylmorpholine oxide N O N O O O NMP N-methylpyrrolidinone NMR NOE NOESY NR or n.r. nuclear magnetic resonance nuclear Overhauser effect nuclear Overhauser effect spectroscopy no reaction N O O S Ns nitrobenzenesulfonyl (nosyl) NO2 Br Nysted reagent Zn cyclo-dibromodi-µ-methylene[µ-(tetrahydrofuran)]trizinc Zn O Zn Br Nu or Nuc nucleophile O OBO O 2,6,7-trioxabicyclo[2.2.2]octyl O O O Ohira-Bestm ann reagent O P dimethyl-1-diazo-2-oxopropylphosphonate N2 OMe OMe oNB o-nitrobenzyl NO2 ORD Oxone optical rotatory dispersion 2KHSO5/KHSO4/K2SO4 P PCC PCR PDC PEG Petasis reagent PG Ph pyridinium chlorochromate polymerase chain reaction pyridinium dichromate polyethylene glycol protective group phenyl Phen 1,10-phenanthroline bis(η5-cyclopentadienyl)dimethyltitanium (PyH)ClCrO3 (PyH)2Cr2O7 Cp2TiMe2 N N O Phth phthaloyl O PIDA PIFA phenyliodonium diacetate phenyliodonium bis(trifluoroacetate) PinBH pinacolborane PhI(OAc)2 PhI(OCOCF3)2 O B H O O Piv pivaloyl PLE pig liver esterase PMB p-methoxybenzyl MeO PMP p-methoxyphenyl MeO pNB p-nitrobenzyl O2N PPA ppb PPL ppm PPTS polyphosphoric acid parts per billion Porcine pancreatic lipase parts per million pyridinium p-toluenesulfonate i Pr isopropyl n normal-propyl Pr (PyH)Ots Me2N Proton sponge 1,8-Bis(dimethylamino)naphthalene psi P.T. PTC pounds per square inch proton transfer phase-transfer catalyst NMe2 O O PTSA p-toluenesulfonic acid Py or Pyr pyridine or pyridyl S OH N Q R R R rac RCAM RCM rds alkyl rectus racemic ring-closing alkyne metathesis ring-closing metathesis rate-determining step Red-Al sodium bis(2-methoxyethoxy)aluminium hydride Na O AlH2 O 2 Rf Rf RI perfluoroalkyl group retension factor in chromatography reflactive index or radio isotope O HO Rochelle salt OK potassium sodium tartrate ONa HO O ROESY ROM ROMP rt S s rotating frame nuclear Overhauser and exchange spectroscopy ring-opening metathesis ring-opening metathesis polymerization room temperature S sinister seconds salen N,N’-ethylenebis(salicylideneiminato) N N OH Schlosser’s base Schrock’s catalyst HO n-BuLi/t-BuOK F3C CF3 F 3C O F3C N Mo O Ph Schwartz’s reagent SEM chloridobis(η5-cyclopentadienyl)hydridozirconium Cp2ZrHCl 2-(trimethylsilyl)ethoxymethyl TMS SES 2-(trimethylsilyl)ethanesulfonyl SET single electron transfer Sia siamyl (s-isoamyl) SOMO STM Stryker’s reagent Super-Hydrid e single occupied molecular orbital scanning tunneling microscope TASF TBAB TBAC TBAF TBAI TBAT TBS TBDMS TBDPS S TMS [Ph3PCuH]6 lithium triethylborohydride LiHBEt3 [(Et2N)3S][Me3SiF2] Bu4NBr n Bu4NCl n Bu4NF n Bu4NI [nBu4N][Ph3SiF2] n tert-butyldimethylsilyl tert-butyldiphenylsilyl O TBHP O O triphenylphosphine-copper(I) hydride hexamer T tris(diethylamino)sulfonium difluorotrimethylsilicate tetrabutylammonium bromide tetrabutylammonium chloride tetrabutylammonium fluoride tetrabutylammonium iodide tetrabutylammonium triphenyldifluorosilicate or O tert-butylhydroperoxide OH S TCDI thiocarbonyldiimidazole N TCA TCE trichloroacetic acid 2,2,2-trichloroethanol Cl3CCO2H Cl3CCH2OH TDAE tetrakis(dimethylamino)ethane TEA TEAB TEAC TEAI triethylamine tetraethylammonium bromide tetraethylammonium chloride tetraethylammonium iodide TEMPO 2,2,6,6-tetramethylpipedinyloxy N N N Me2N NMe2 Me2N NMe2 Et3N Et4NBr Et4NCl Et4NI N O Teoc 2-(trimethylsilyl)ethoxycarbonyl TMS O O TES temp. triethylsilyl temperature O O Tf trifluoromethanesulfonyl TFA TFAA TFE trifluoroacetic acid trifluoroacetic anhydride 2,2,2-trifluoroethanol Thexyl tert-hexyl THF tetrahydrofuran F3C S CF3CO2H (CF3CO)2O CF3CH2OH O THP or tetrahydropyrane or 2-tetrahydropyranyl O O TIPS TLC TM TMEDA triisopropylsilyl thin layer chromatography target molecule N,N,N’,N’-tetramethylethylenediamine Me2 N HN TMG 1,1,3,3-tetramethylguanidine NMe2 NMe2 Me2N TMS trimethylsilyl or tetramethylsilane O TosMIC toluenesulfonylmethyl isocyanide TOF tol or tolyl TON Ts time-of-flight or turnover frequency methylphenyl turnover number p-toluenesulfonyl Tp trispyrazoryl borate Tp* O S B H B tris(2,4-dimethylpyrazoryl)borate 3 N N 3 n tetra-n-propylammonium perruthenate triphenylmethyl Pr4N RuO4 Ph3C- trien triethylenetetramine H 2N Triton B Benzyltrimethylammonium hydroxide BnNMe3OH Troc 2,2,2-trichloroethoxycarbonyl Cl3C N H N H O O transition state U UV C N N H TPAP Tr TS N ultraviolet V vic vicinal Vilsmeier’s reagent N-Chloromethylene-N,N-dimethyl ammonium chloride N Cl Cl NH2 W Weinreb amide O N,O-dimethylhydroxamic acids R OMe N Me O Wieland-Mie scher ketone 8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione O Wilkinson’s chlorotris(triphenylphosphine)rhodium(I) catalyst WSC or water-soluble carbodiimide WSCI X XAFS X-ray absorption fine structure XANES X-ray absorption near edge strucuture XRD X-ray diffraction xyl or xylyl 3,5-dimethylphenyl Y y. yield Z RhCl(PPh3)3 N Ph Z C N O benzyloxycarbonyl O Z zusammen NMe2 -HCl Ligand Name and Structures BINAP (Ar = Ph) PAr2 tol-BINAP (Ar = p-tolyl) PAr2 DM-BINAP (Ar = 3.5-xylyl) O O N R O N R BOX O H8 -BINAP N R PyBOX PPh2 R PPh2 R F O DIFLUORPHOS DANP O R N PheBOX R O PPh2 F O PPh2 F O PPh2 PPh2 O N R F O O O N N O O PPh2 PPh2 OMe N O Me-Sinophos (R = Me) Cy-Sinophos (R = Cy) MeO MeO O PAr2 PAr2 N O PAr 2 PAr 2 O O SEGPHOS (Ar = Ph) DM-SEGPHOS (Ar = 3,5-xylyl) DMM-SEGPHOS (Ar = 3,5-Me2-4-MeO-C6H2 ) DTBM-SEGPHOS (Ar = 3,5- tBu2-4-MeO-C6H2) OMe CTH-P-Phos (Ar = Ph) CTH-Xyl-P-Phos (Ar = 3,5-xylyl) PPh2 OMe MOP R PPh2 R P P R R Me-DuPHOS (R = Me) Et-DuPHOS (R = Et) i Pr-DuPHOS (R = iPr) PPh2 PPh2 N PHANEPHOS Ph2P H PPh2 PPh2 BDPP H P H PPh2 P H BICP Tangphos O O O * O P O * P PPh2 PPh2 O PPh2 Norphos R PHOX Fe PAr2 PAr2 BIPHEP (Ar = Ph) Xyl-BIPHEP (Ar = 3,5-xylyl) PPh2 Fe PPh2 Reetz-1 DIOP MeO MeO PPh2 O dppf HO = BINOL HO * PR'2 R2P Fe PR2 Ph2P Fe H Josiphos-1 (R=Ph, R'=Cy) Josiphos-2 (R=Ph, R'=tBu) Josiphos-3 (R=R'=Cy) Josiphos-4 (R=Ph, R'=Xyl ) O H NMe2 Ph R2P Fe Taniaphos-Ph (T1; R=Ph) Taniaphos-Cy (T2; R=Cy) Et O N t PPh2 Ph2 P Fe Me2N R2P Walphos-1 (R=3,5-(CF3)2-C6H4) Mandyphos-1 (R=Ph) Mandyphos-2 (R=Cy) Walphos-2 (R=Ph) NH HN Trost Ligand PR2 NMe2 Ph R2P Bu OH HO t Bu Salen tBu P Et N Fe P t Bu Et Et Et-FerroTANE
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