Substitution on Carbenoid Carbon of α-Halocyclopropyllithium. A Novel Stereoselective Synthesis of Geminally Substituted Cyclopropanes

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Abstract
The halogen atom of the title carbenoids is susceptible to displacement by butyllithium. 1-Butyl-1-lithiocyclopropanes are formed, in which the butyl group occupies the less hindered site trans or exo position). The new reaction provides a means for the preparation of geminally disubstituted cyclopropanes with high degree of stereoselectivity.