Critical importance of leaving group 'softness' in nucleophilic ring closure reactions of ambident anions to 1,2-diazetidines

被引：12

作者：

Brown, Michael J. ^{[1
]}

Clarkson, Guy J. ^{[1
]}

Fox, David J. ^{[1
]}

Inglis, Graham G. ^{[2
]}

Shipman, Michael ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

BETA-LACTAM; REACTIVITY; ACIDS; DERIVATIVES; HYDRAZINES; CHEMISTRY; HARD;

D O I：

10.1016/j.tetlet.2009.11.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly strained, four-membered 1,2-diazetidine rings are produced in good yields (50-98%) in nucleophilic ring closure reactions provided 'soft' leaving groups such as iodide are used, a finding that can be rationalised in terms of the Hard Soft Acids and Bases principle. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：382 / 384

页数：3