Electrophilic cyclopropanes reactivity

This chapter will deal mainly with the synthesis and reactivity of electrophilic cyclopropanes and only these procedures and reactions will be investigated which give rise to cyclopropanes geminally substituted with two EWGs. Nevertheless, the preparation of monoactivated cyclopropanes will be mentioned to some extent because a number of procedures for the synthesis of electrophilic cyclopropanes have been developed for cyclopropanes bearing one EWG. Therefore, the synthesis and reactivity of the latter compounds cannot be excluded, due to the close relationship and the numerous studies concerning reaction mechanisms for these compounds. 

Synthesis and reactivity of electrophilic cyclopropanes b. MIRC reactions with the leaving group in the attacking nucleophile... 

Although electrophilic cyclopropane derivatives have been widely used in the synthesis of natural products especially in the total synthesis of polycarbocyclic sesquiterpenes no systematic review describing the reactivity of electrophilic cyclopropanes (sensu strictu) towards various reagents has appeared. In addition to the excellent review of Danishefsky ... 

Few reports deal with the reactivity of alkoxides and phenoxides with electrophilic cyclopropanes. Treatment of the cyclopropane-1,1-dicarboxylate (500) with sodium... 

The reactivity of electrophilic cyclopropanes towards S- and Se-nucleophiles shows great resemblance to the reaction with O-nucleophiles. Treatment of the cyclopropanes with thiophenolates or selenolates results in ring-opening (equation 181), The reaction of... 

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