NEIGHBORING GROUP PARTICIPATION IN REACTIONS OF ALCOHOLS WITH LEAD TETRAACETATE

被引：19
作者：
MORAND, P
KAUFMAN, M
机构：
[1] Department of Chemistry, University of Ottawa, Ottawa
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 07期
关键词：
D O I：
10.1021/jo01259a032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The participation of the neighboring group in two related steroidal α-methoxy alcohols has been studied. 3β-Acetoxy-5α-methoxycholestan-6β-ol, 2a, and 3β-acetoxy-6β-methoxycholestan-oα-ol, 5a, were prepared by cleavage of the corresponding 5β,6β- and 5α,6α-epoxides, 1a and 1b, in methanol in the presence of acetic acid or boron trifluoride. The course of the lead tetraacetate oxidation of these alcohols was strongly influenced by the adjacent methoxyl group. The structures of the products isolated have been established and mechanisms for their formation are discussed. © 1969, American Chemical Society. All rights reserved.
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页码：2175 / &
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