Survey of Chemical Reactivity of C60, Electrophile and Dieno—polarophile Par Excellence

Buckminsterfullerene, C60, was found to add a large variety of neutral and charged nucleophiles, a couple of dienes, and a number of dipoles. The reagents mentioned within are propylamine, dodecylamine, tert-butylamine, ethylenediamine, morpholine, triethyl phosphite, hydride (lithium triethyl borohydride), phenyllithium, phenylmagnesium bromide, tert-butyllithium, tert-butylmagnesium bromide, anthracene, cyclopentadiene, p-nitrophenylazide, ethyl diazoacetate, phenyldiazomethane, diphenyldiazomethane, and the ylide (CH3)2S+CH-CO2Et. When a large molar excess of reagent relative to fullerene is used, as many as 10—12 new bonds are formed. For primary amine addition (with the exception of tert-butylamine), the mechanism involves single-electron transfer as a first step. Mass spectrometry shows facile reactivity of C60 in the gas phase with CH4 in both positive and negative ionization.