SYNTHESIS AND STEREOCHEMISTRY OF AN OPTICALLY-ACTIVE SELENONIUM YLIDE - X-RAY MOLECULAR-STRUCTURE OF (+)SE-(4'-[(-)-MENTHYLOXYCARBONYL]PHENYL)(METHYL)SELENONIUM 4,4-DIMETHYL-2,6-DIOXOCYCLOHEXYLIDE

被引:40
作者
KAMIGATA, N
NAKAMURA, Y
KIKUCHI, K
IKEMOTO, I
SHIMIZU, T
MATSUYAMA, H
机构
[1] Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Minami-osawa, Hachioji
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 13期
关键词
D O I
10.1039/p19920001721
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fractional recrystallization of diastereoisomeric {4'-[(-)-menthyloxycarbonyl]phenyl}(methyl)-selenonium selenonium 4,4-dimethyl-2,6-dioxocyclohexylide from hexane-diethyl ether gave the optically pure (+)-selenonium ylide as stable crystals. The absolute configuration around the selenium atom was determined to be R by X-ray crystallographic analysis. The epimerization of the optically active selenonium ylide by pyramidal inversion was studied.
引用
收藏
页码:1721 / 1728
页数:8
相关论文
共 47 条
[1]   SYNTHESIS OF OPTICALLY-ACTIVE DIALKYLARYLSULFONIUM SALTS FROM ALKYL ARYL SULFOXIDES [J].
ANDERSEN, KK ;
CARET, RL ;
LADD, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) :3096-3100
[2]   OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].
ANDERSEN, KK ;
FOLEY, JW ;
GAFFIELD, W ;
PAPANIKOLAU, NE ;
PERKINS, RI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+
[3]  
ANDERSEN KK, 1981, CHEM SULFONIUM GROUP, P229
[4]  
[Anonymous], 1974, INT TABLES XRAY CRYS, VIV
[5]  
BALDWIN JE, 1986, ORGANIC CHEM SERIES, V4
[6]   SYNTHESIS AND REACTIONS OF CHIRAL SULFONIUM YLIDS [J].
CAMPBELL, SJ ;
DARWISH, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (16) :2953-2959
[7]   CRYSTAL AND MOLECULAR STRUCTURE OF 2-DIMETHYLSULFURANYLIDENEMALONONITRILE [J].
CHRISTENSEN, AT ;
WITMORE, WG .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1969, B 25 :73-+
[8]   CARBODIIMIDE-SULFOXIDE REACTIONS .7. SYNTHESIS OF STABILIZED SULFONIUM YLIDES [J].
COOK, AF ;
MOFFATT, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (03) :740-&
[9]   1ST SYNTHESIS OF SIMPLE OPTICALLY-ACTIVE SELENOXIDES [J].
DAVIS, FA ;
BILLMERS, JM ;
STRINGER, OD .
TETRAHEDRON LETTERS, 1983, 24 (31) :3191-3194
[10]   STEREOCHEMISTRY OF NUCLEOPHILIC SUBSTITUTION AT SULFUR . STEREOSPECIFIC SYNTHESIS OF AN OPTICALLY ACTIVE SULFILIMINE [J].
DAY, J ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (19) :4398-&