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 wi...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.展开更多
Transition-metal-salt-mediated radical reactions of fullerenes have attracted extensive attention as a new and important method for fullerene functionalization. The application of relatively cheap and easily available...Transition-metal-salt-mediated radical reactions of fullerenes have attracted extensive attention as a new and important method for fullerene functionalization. The application of relatively cheap and easily available ferric perchlorate (Fe(ClO 4 ) 3 ) to the synthesis of [60]fullerene (C 60 ) has demonstrated remarkable advantages and afforded a series of novel fullerene derivatives. In this review we present our recent progress in this area and summarize the reactions of C 60 with malonate esters, β-keto esters, nitriles, aldehydes/ketones, and arylboronic acids in the presence of Fe(ClO 4 ) 3 to afford the C 60-fused disubstituted lactones, C 60-fused hemiketal, C 60-fused dihydrofuran, C 60-fused oxazoles, C 60-fused 1,3-dioxolanes, and fullerenyl boronic esters. The possible reaction mechanisms for the above-mentioned reactions are also described in detail.展开更多
基金supported by the Research Fund for the Doctoral Program of Higher Education of China (200803580019)China Postdoctoral Science Foundation (20080440715)K.C.Wong Education Foundation,Hong Kong
文摘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.
基金supported by the National Natural Science Foundation of China (20972145, 21132007, 21102041)National Basic Research Program of China (2011CB921402)Scientific Research Foundation of Education Commission of Hubei Province (Q20120113)
文摘Transition-metal-salt-mediated radical reactions of fullerenes have attracted extensive attention as a new and important method for fullerene functionalization. The application of relatively cheap and easily available ferric perchlorate (Fe(ClO 4 ) 3 ) to the synthesis of [60]fullerene (C 60 ) has demonstrated remarkable advantages and afforded a series of novel fullerene derivatives. In this review we present our recent progress in this area and summarize the reactions of C 60 with malonate esters, β-keto esters, nitriles, aldehydes/ketones, and arylboronic acids in the presence of Fe(ClO 4 ) 3 to afford the C 60-fused disubstituted lactones, C 60-fused hemiketal, C 60-fused dihydrofuran, C 60-fused oxazoles, C 60-fused 1,3-dioxolanes, and fullerenyl boronic esters. The possible reaction mechanisms for the above-mentioned reactions are also described in detail.
