MECHANISM OF ACID-CATALYZED DEHYDRATION OF 1,2-DIPHENYLETHANOL

被引：30

作者：

NOYCE, DS

HARTTER, DR

POLLACK, RM

机构：

[1] Department of Chemistry, University of California, Berkeley

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 14期

关键词：

D O I：

10.1021/ja01016a034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The acid-catalyzed dehydration of 1,2-diphenylethanol (1) proceeds readily in 50-60% sulfuric acid, and affords trans-stilbene. The reaction is very sharply acid catalyzed, a plot of log k vs. -H0 having a slope of 1.32. Racemization of active 1,2-diphenylethanol is 58 times more rapid than dehydration. In deuteriosulfuric acid, dehydration is moee rapid. The rate of dehydration of 2-deuterio-l,2-diphenylethanol is smaller than that of 1, kH/kD being 1.83. All of these facts are consistent with a reaction pathway involving the reversible formation of the 1,2-diphenylethyl cation followed by rate-limiting proton loss to give trans-stilbene. © 1968, American Chemical Society. All rights reserved.

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页码：3791 / &

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