BF3·Et2O- or DMAP-catalyzed double nucleophilic substitution reaction of aziridinofullerenes with sulfamides or amidines

J Org Chem. 2014 Dec 5;79(23):11744-9. doi: 10.1021/jo5020596. Epub 2014 Nov 17.

Abstract

BF3·Et2O-catalyzed double nucleophilic substitution reaction of N-tosylaziridinofullerene with sulfamides has been exploited for the easy preparation of cyclic sulfamide-fused fullerene derivatives. Moreover, the Lewis base catalyzed double amination of N-tosylaziridinofullerene, with amidines as the diamine source, is demonstrated for the first time. The present methods provide new routes to cyclic 1,2-diaminated [60]fullerenes.