VINYLIC CATIONS FROM SOLVOLYSIS .2. STEREOCHEMISTRY OF SN1 REACTION OF 1,2-DIANISYL-2-PHENYLVINYL HALIDES

被引：75

作者：

RAPPOPOR.Z

APELOIG, Y

机构：

[1] Department of Organic Chemistry, Hebrew University, Jerusalem

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1969年 / 91卷 / 24期

关键词：

D O I：

10.1021/ja01052a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

cis- and trans-1,2-dianisyl-2-phenylvinyl bromide and chloride were prepared and their stereochemistry determined. Solvolysis in the presence of benzylthiolate and p-toluenethiolate ions in 80% ethanol, chloride ion in acetic acid and in dimethylformamide, and acetate ion in acetic acid gave cis and trans products derived from capture of the intermediate cation by the nucleophile, in 1:1 ratios. 1,2-Dianisyl-2-phenylethanone is formed on solvolysis in aqueous ethanol, formic acid, and dimethylformamide. Predictions regarding the stereochemistry of the Sn1 vinylic substitution are discussed and it is concluded that the product-forming intermediate is a linear sp hybridized dissociated vinyl cation. © 1969, American Chemical Society. All rights reserved.

引用

页码：6734 / +

页数：1

共 47 条

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