STEREOCHEMISTRY OF SOLVOLYSIS OF 2-PHENYLETHYL SULFONATE ESTERS - PHENONIUM ION-EQUILIBRATING CLASSICAL IONS PROBLEM

被引：32

作者：

JABLONSKI, RJ

SNYDER, EI

机构：

[1] Department of Chemistry, University of Connecticut, Storrs

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1969年 / 91卷 / 16期

关键词：

D O I：

10.1021/ja01044a022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Solvolysis of diastereomerically pure PhCHDCHD0SO2Ar leads to product in which the extent of retention of diastereomeric configuration is in all cases twice the extent of label rearrangement in PhCH2C*H2OTs. This relation, which is uniquely required by a symmetric phenonium ion, has been observed for 5,15, 44, and 50% rearrangement attending solvolysis and 27% rearrangement attending deamination. Detailed kinetic inspection of the equilibrating classical ion scheme suggests that although it can account for the entropy spread associated with the ks k∆ routes it cannot account adequately for other related observations. © 1969, American Chemical Society. All rights reserved.

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页码：4445 / +

页数：1

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