The Journal of Organic Chemistry

gem-Dialkoxy Effect in Radical Cyclizations To Form Cyclopropane Derivatives: Unusual Oxidation of a Dialkoxyalkyl Radical

ME Jung, M Kiankarimi

Index: Jung, Michael E.; Kiankarimi, Mehrak Journal of Organic Chemistry, 1995 , vol. 60, # 21 p. 7013 - 7014

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Citation Number: 13

Abstract

Recently we published an example of the synthetic utility of the gem-dialkoxy effect for the efficient preparation of strained four-membered rings by radical cyclizati~ n.~ As shown below, under similar conditions cyclization of the ethyl 6-bromo-2-hexenoates la-c gave either the acyclic 2a-c or cyclic 3a-c products. The dihydrido substrate la gave only the acyclic product 2a. gemdimethyl substitution, eg, lb, increased the amount of cyclic ...