TERMINATION OF MN(III)-BASED OXIDATIVE FREE-RADICAL CYCLIZATIONS BY ADDITION TO NITRILES - FORMATION OF CYCLOPENTANONES AND CYCLOHEXANONES

被引：49

作者：

SNIDER, BB

BUCKMAN, BO

机构：

[1] Department of Chemistry, Brandeis University, Waltham

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 01期

关键词：

D O I：

10.1021/jo00027a056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mn(III)-based oxidative free-radical tandem cyclizations and annulations can be terminated by addition to nitriles. Cyclopentanones 20a (51%), 24a (57%), and 32a (54%) are formed in good yield. Annulation to give cyclohexanone 32b (41%) proceeds in moderate yield, although 20b (8%) and 24b (13%) are formed in poor yield in tandem cyclizations. Pyridine 39 (15%) is formed in ethanol by condensation of the enamine tautomer 37 of imine 31a with the oxidation byproduct 33a produced from radical 29a.

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页码：322 / 326

页数：5

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