Radical Reactions of C 60

Photochemically generated benzyl radicals react with C 60 producing radical and nonradical adducts R n C 60 (R = C 6 H 5 CH 2 ) with n = 1 to at least 15. The radical adducts with n = 3 and 5 are stable above 50°C and have been identified by electron spin resonance (ESR) spectroscopy as the allylic R 3 C 60 . (3) and cyclopentadienyl R 5 C 60 . (5) radicals. The unpaired electrons are highly localized on the C 60 surface. The extraordinary stability of these radicals can be attributed to the steric protection of the surface radical sites by the surrounding benzyl substituents. Photochemically generated methyl radicals also add readily to C 60 . Mass spectrometric analyses show the formation of (CH 3 ) n C 60 with n = 1 to at least 34.