Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones

被引：91

作者：

Anderson, AM ^{[1
]}

Blazek, JM ^{[1
]}

Garg, P ^{[1
]}

Payne, BJ ^{[1
]}

Mohan, RS ^{[1
]}

机构：

[1] Illinois Wesleyan Univ, Dept Chem, Bloomington, IL 61701 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 10期

关键词：

bismuth; bismuth compounds; epoxides; rearrangements;

D O I：

10.1016/S0040-4039(99)02330-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement in the presence of 10-50 mol% bismuth(III) oxide perchlorate, BiOClO4.x H2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C-O bond is formed. BiOClO4 x H2O is relatively non-toxic, insensitive to air and inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3 . Et2O or InCl3 currently used to effect epoxide rearrangements. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1527 / 1530

页数：4

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