Formation of a propellanone in the solvolysis of a 2-oxo bicyclic bridgehead compound

Abstract

Methanolysis of 2-oxobicyclo[3.3.1]non-1-yl triflate gives the corresponding [3.3.1]-propellanone 2 in 15% yield. Primary factors involved in the reaction would be the marked electrophilicity of the destabilized 2-oxo bridgehead carbocation and stabilization of the cyclopropane ring of 2 by the π acceptor carbonyl group.