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
    DESHMUKH, M
    DUNACH, E
    JUGE, S
    KAGAN, HB
    [J]. 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
    HARGER, MJP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (10): : 1505 - 1511
  • [6] NEW APPROACHES FOR ASYMMETRIC-SYNTHESIS OF SULFOXIDES
    KAGAN, HB
    REBIERE, F
    SAMUEL, O
    [J]. 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
    MIKOLAJCZYK, M
    OMELANCZUK, J
    PERLIKOWSKA, W
    MARKOVSKI, LN
    ROMANENKO, VD
    RUBAN, AV
    DRAPAILO, AB
    [J]. 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
    OMELANZCUK, J
    SOPCHIK, AE
    LEE, SG
    AKUTAGAWA, K
    CAIRNS, SM
    BENTRUDE, WG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) : 6908 - 6909
  • [10] Pirkle W.H., 1982, TOP STEREOCHEM, V13, P263