The chemical retro-Bingel reaction: selective removal of bis(alkoxycarbonyl)methano addends from C60 and C70 with amalgamated magnesium

Abstract

Bis(alkoxycarbonyl)methano addends are removed from C₆₀ and C₇₀ derivatives by reaction with amalgamated magnesium in dry THF; this facile and selective retro-Bingel reaction, which leaves pyrrolidine rings fused to C₆₀ intact, opens up the possibility of using bis(alkoxycarbonyl)methano addends as protecting and reversible directing groups in the regioselective multiple functionalization of fullerenes.