STEREOCHEMISTRY OF IODINE ADDITION TO ACETYLENES

被引：47

作者：

HOLLINS, RA ^{[1
]}

CAMPOS, MPA ^{[1
]}

机构：

[1] INST MIL ENGENHARIA,RIO DE JANEIRO,RJ,BRAZIL

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 22期

关键词：

D O I：

10.1021/jo01336a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have studied the addition of iodine to a series of acetylenic substrates, including derivatives of propiolic acid, propyne, and phenylacetylene. Configurations of the resulting diiodoolefins were established, using and 13C NMR analysis. In all cases, products of configuration E were obtained, and only with alkyl propiolates was there concomitant formation of the Z isomer. Additional evidence supporting the assignments for allylic products was obtained by the interconversion of these products. Application of a simple pairwise additivity of substituent shielding parameters allowed for a better agreement between calculated and observed 13C chemical shifts for various products. © 1979, American Chemical Society. All rights reserved.

引用

页码：3931 / 3934

页数：4

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