CHIRAL T-BUTYLPHENYLPHOSPHINOTHIOIC ACID - A NEW NMR SOLVATING AGENT FOR DETERMINATION OF ENANTIOMERIC EXCESSES OF SULFOXIDES

被引:48
作者
DRABOWICZ, J [1 ]
DUDZINSKI, B [1 ]
MIKOLAJCZYK, M [1 ]
机构
[1] POLISH ACAD SCI,CTR MOLEC & MACROMOLEC STUDIES,DEPT ORGAN SULFUR CPDS,SIENKIEWICZA 112,PL-90362 LODZ,POLAND
关键词
D O I
10.1016/S0957-4166(00)82079-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(-)-(S)-t-Butylphenylphosphinothioic acid forms with dialkyl and aralkyl sulfoxides diastereomeric dynamic systems the H-1 NMR spectra of which show typical anisochronism of the diastereotopic S-alkyl groups. The magnetic nonequivalence observed even for delta protons, is great enough to determine the e.e. values of sulfoxides having relatively long alkyl chains (e.g. n-butyl)
引用
收藏
页码:1231 / 1234
页数:4
相关论文
共 12 条
[1]  
BENTRUDE WG, 1983, J AM CHEM SOC, P105
[2]   A CONVENIENT FAMILY OF CHIRAL SHIFT-REAGENTS FOR MEASUREMENT OF ENANTIOMERIC EXCESSES OF SULFOXIDES [J].
DESHMUKH, M ;
DUNACH, E ;
JUGE, S ;
KAGAN, HB .
TETRAHEDRON LETTERS, 1984, 25 (32) :3467-3470
[3]  
DRABOWICZ J, IN PRESS J CHEM SOC
[4]  
Drabowicz J., 1989, SULFUR LETT, V10, P37
[5]   THE PROTON MAGNETIC-RESONANCE SPECTRA OF CHIRAL PHOSPHINATE ESTERS - CHEMICAL-SHIFT NON-EQUIVALENCE OF ENANTIOMERS INDUCED BY OPTICALLY-ACTIVE PHOSPHINOTHIOIC ACIDS [J].
HARGER, MJP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (10) :1505-1511
[6]   NEW APPROACHES FOR ASYMMETRIC-SYNTHESIS OF SULFOXIDES [J].
KAGAN, HB ;
REBIERE, F ;
SAMUEL, O .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 58 (1-4) :89-110
[7]   A NEW ENANTIOSELECTIVE ASYMMETRIC-SYNTHESIS OF TRI-CO-ORDINATE PHOSPHORUS-COMPOUNDS FROM DI-CO-ORDINATE LAMBDA-3-ARYL(ALKYL)IMINOPHOSPHINES [J].
MIKOLAJCZYK, M ;
OMELANCZUK, J ;
PERLIKOWSKA, W ;
MARKOVSKI, LN ;
ROMANENKO, VD ;
RUBAN, AV ;
DRAPAILO, AB .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 36 (3-4) :267-270
[8]  
Mikolajczyk M., 1982, TOP STEREOCHEM, V13, P333
[9]   PHOTO-ARBUZOV REARRANGEMENTS OF BENZYL PHOSPHITES [J].
OMELANZCUK, J ;
SOPCHIK, AE ;
LEE, SG ;
AKUTAGAWA, K ;
CAIRNS, SM ;
BENTRUDE, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6908-6909
[10]  
Pirkle W.H., 1982, TOP STEREOCHEM, V13, P263