The Journal of Organic Chemistry

1-Alkenylcycloalkoxy radical chemistry. A two-carbon ring expansion methodology

P Galatsis, SD Millan, T Faber

Index: Galatsis, Paul; Millan, Scott D.; Faber, Tim Journal of Organic Chemistry, 1993 , vol. 58, # 5 p. 1215 - 1220

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Citation Number: 38

Abstract

The exploitation of alkoxy radicals derived from 1-ethenylcycloalkanols for use in a two- carbon ring expansion protocol was proposed. Direct one-pot alkoxy radical-mediated fragmentation-cyclization was not feasible since the reactive intermediate was quenched by iodine in the reaction mixture. However, via the use of iodo epoxides 3, the tandem fragmentation-cyclization sequence could be accomplished. This afforded ring-expanded ...