Manganese(Ⅲ) acetate-mediated radical reaction of [60]fullerene with bromoacetic acid,3-chloropropionic acid or 1-naphthylacetic acid

The manganese(Ⅲ) acetate-mediated radical reaction of [60]fullerene (C60) with three carboxylic acids,that is,bromoacetic acid,3-chloropropionic acid,and 1-naphthylacetic acid,was investigated. The reaction of C60 with bromoacetic acid in the presence of 4-(dimethylamino)pyridine afforded the anticipated C60-fused lactone,while the reaction with 3-chloropropionic acid unexpectedly led to the formation of a novel C60-fused lactone with the loss of one molecule of HCl. Interestingly,the reaction with 1-naphthylacetic acid under similar conditions gave both C60-fused lactone and 1,4-adduct,yet each of them could be selectively obtained by controlling reaction conditions. It was also observed that the C60-fused lactone bearing a bulky naphthyl group existed as two isomers.