Reaction of Cage-opened Fullerene Derivative with Grignard Reagents and Subsequent Transannular Cyclization

Abstract

Abstract 1,2-Addition of methyl and allyl Grignard reagents to a cage-opened fullerene derivative 2a selectively proceeded at −20 °C in THF at one of the two carbonyl groups. Under acidic conditions, the resulting alcohol underwent a transannular cyclization. The elevated LUMO levels of these products were shown by electrochemical and theoretical investigations.