REDUCTIVE ACETOXYLATION ON ALPHA, ALPHA'-DIBROMOCYCLOALKANONES BY ULTRASONICALLY DISPERSED MERCURY

被引：8

作者：

FRY, AJ

DONALDSON, WA

GINSBURG, GS

机构：

[1] Hall-Atwater Laboratories of Chemistry, Wesleyan University, Middletown

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 03期

关键词：

D O I：

10.1021/jo01317a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The α, α's-dibromocycloalkanones of ring size 5-12 were reduced by ultrasonically dispersed mercury in acetic acid. Products were the corresponding cycloalkanone and α-acetoxycycloalkanone. The ratio of these two is quite sensitive to ring size, and this fact is used to support the intermediate formation of 2-hydroxyallyl cations as precursors of the keto acetates. Molecular mechanics calculations support the proposed mechanism. © 1979, American Chemical Society. All rights reserved.

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页码：349 / 352

页数：4

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