Efficient electrocatalytic intramolecular anion radical cyclobutanation reactions

被引：20

作者：

Felton, GAN ^{[1
]}

Bauld, NL ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 48期

关键词：

anion radical; cyclobutanation; catalytic; electrochemical reduction; pericyclic; electrogenerated base;

D O I：

10.1016/j.tet.2004.08.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrochemically initiated, intramolecular anion radical cyclobutanations of bis(enones) and related substrates are presented. The formation of novel anion radical Diels-Alder adducts in minor amounts is also observed. Total yields of pericyclic products, which include both cis- and trans-cyclobutanes and a single Diels-Alder adduct, are generally high (51-88%), with electrocatalytic factors in the range of 1.5-5. Mechanistically, strong evidence for the intervention of distonic anion radical intermediates as precursors of both types of pericyclic products is presented. The scope and limitations of these reactions are rather extensively explored and defined, and in particular the tendency, in some cases, for electrogenerated base-catalyzed reactions to compete with these anion radical pericyclic reactions. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：10999 / 11010

页数：12

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