A CORRELATION BETWEEN THE ABSOLUTE-CONFIGURATIONS OF ACYCLIC ALIPHATIC AND BENZYLIC SECONDARY ALCOHOLS AND THE OPTICAL ROTATIONS OF THEIR 2,4-DINITROBENZENESULFENYL DERIVATIVES

被引：6

作者：

CRAINE, LE ^{[1
]}

BICKNELL, LK ^{[1
]}

MAILLOUX, RC ^{[1
]}

MARK, JP ^{[1
]}

MITCHELL, SA ^{[1
]}

VICENTE, SR ^{[1
]}

JASINSKI, JP ^{[1
]}

WOUDENBERG, RC ^{[1
]}

机构：

[1] KEENE STATE COLL,DEPT CHEM,KEENE,NH 03431

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2,4-dinitrobenzenesulfenate esters 2a-v of 11 acyclic aliphatic and 11 benzylic chiral secondary alcohols of known configuration were synthesized, and their sodium D line optical rotations and CD spectra were determined. The sign of the sodium D line rotations of the derivatives was consistently correlated with the absolute configuration of the carbinol carbon in the original alcohols. The CD spectra exhibited optically active transitions in the 320-400-nm region that corresponded in sign to the sodium D line optical rotations and were strong enough to dominate the sign of rotation at the sodium D line. Thus the optical rotations and CD spectra of these sulfenate ester derivatives are diagnostic for the absolute configurations of chiral secondary acyclic aliphatic and benzylic alcohols.

引用

页码：1251 / 1258

页数：8

共 22 条

[1] THE CHEMISTRY OF 1,2-DITHIOLANE (TRIMETHYLENE DISULFIDE) AS A MODEL FOR THE PRIMARY QUANTUM CONVERSION ACT IN PHOTOSYNTHESIS [J].