SYNTHESIS AND PHYSICAL-PROPERTIES OF A SERIES OF OPTICALLY-ACTIVE SUBSTITUTED TRANS-STILBENE OXIDES

被引:40
作者
IMUTA, M [1 ]
ZIFFER, H [1 ]
机构
[1] NIAMDD,CHEM PHYS LAB,BETHESDA,MD 20014
关键词
D O I
10.1021/jo01328a038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of substituted threo-(R, R)-diphenylethanediols, prepared by microbial reduction of the appropriate benzil derivatives, was converted to the corresponding trans-stilbene oxides. The positive CD bands at 230-235 nm exhibited by these compounds agree in sign and magnitude with those predicted from a model developed by Mason et al. for trans-stilbene oxide. Microbial reduction of desyl chloride was shown to yield the threo-(R, R)-chlorohydrin, thus establishing a route for the preparation of optically active cis-stilbene oxides. The chemical shifts and coupling constants for the 1H NMR and 13C NMR spectra of several sets of cis-and trans-stilbene oxides are reported. © 1979, American Chemical Society. All rights reserved.
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页码:2505 / 2509
页数:5
相关论文
共 19 条
[1]   REACTION OF CIS-STILBENE AND TRANS-STILBENE WITH PEROXYBENZOIC ACID IN THE PRESENCE OF TRICHLOROACETIC ACID [J].
BERTI, G ;
BOTTARI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (08) :1286-1292
[2]   STEREOCHEMISTRY OF ADDITIONS OF ACIDS TO STILBENE AND STYRENE OXIDES [J].
BERTI, G ;
BOTTARI, F ;
FERRARIN.PL ;
MACCHIA, B .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4091-&
[4]  
CECCARELLI G, 1970, ORG MAGN RESONANCE, V2, P379
[5]   OPTICALLY-ACTIVE 4-SUBSTITUTED CIS-1,2-DIPHENYLETHYLENE OXIDES AND RELATED 1,2-DIPHENYLETHANE DIOLS [J].
DANSETTE, PM ;
ZIFFER, H ;
JERINA, DM .
TETRAHEDRON, 1976, 32 (17) :2071-2074
[6]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF SOME EPOXIDES [J].
DAVIES, SG ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (08) :861-863
[7]   C-13 NUCLEAR MAGNETIC-RESONANCE STUDIES ON POLYEPOXIDES DERIVED FROM SINGLET OXYGEN ADDITION TO INDENES [J].
EASTON, NR ;
ANET, FAL ;
BURNS, PA ;
FOOTE, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (12) :3945-3948
[8]   THE LITHIUM ALUMINUM HYDRIDE REDUCTION OF PARA-SUBSTITUTED STILBENE OXIDES [J].
FELDSTEIN, A ;
VANDERWERF, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (06) :1626-1631
[9]   CIRCULAR DICHROISM AND ABSOLUTE CONFIGURATION OF (+)-TRANS-STILBENE OXIDE [J].
GOTTAREL.G ;
MASON, SF ;
TORRE, G .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07) :1349-&
[10]  
GOULD ES, 1959, MECHANISM STRUCTURE, P183