Synthesis of C₆₀ Alkanoyl Chlorides

Significance

A facile method for the synthesis of reactive C₆₀ alkanoyl chlorides is reported. The procedure involves the cyclopropanation of the fullerene with a sulfonium ylide to form the tert-butyl ester with decent yields (53-65%). Hydrolysis of the ester with p-TsOH and conversion into the acid chloride with SOCl₂ provided the desired products with good yields (66-98%). Of the four acid chlorides reported, the derivatives with R = Me, Bn, and Ph are novel compounds. The reaction of alkanoyl chlorides with alcohols and amines under basic conditions gave the corresponding esters and amides with poor to excellent yields.