Allyl and 2-Cyclopropylethyl Rearrangements in the Reaction of 1-Alkenylaluminums with Diiodomethane/Triethylaluminum Reagent

Abstract

The reaction of diiodomethane and triethylaluminum with substituted 1-alkenylaluminums obtained by the Zr-catalyzed carbo- or cycloalumination of mono- or dialkyl-substituted alkynes resulted in the selective formation of di- and tetrasubstituted cyclopropanes. 1-Alkenylaluminums prepared from substituted propargylamines reacted with diiodomethane and triethylaluminum to give substituted allylamines. A plausible mechanism for the reaction of the 1-alkenylaluminums with diiodomethane/triethylaluminum is proposed.

Key words

alkenylaluminums - aluminum carbenoids - cyclopropanation - rearrangement - allylic amines

• References and Notes

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