AZA-AZIRIDINOFULLERENE - INTERCONVERSION BETWEEN AZA-AZIRIDINOFULLERENE AND BISAZAFULLEROID

The synthesis and spectroscopic characterization of a novel bisazafull eroid (12) and aza-aziridinofulleroid (13) are described. Treatment of C-60 fullerene with the C-2-chiral bisazide 11 in refluxing chloroben zene afforded bisazafulleroid 12 in 20% yield, When a solution of 12 w as exposed to ambient light a quantitative conversion to the more pola r 13, in which the two imino groups add at both [5,6] and [6,6]-ring j unctions, was observed. The two compounds exhibited characteristic abs orption profiles in the electronic spectra and also showed distinct CD curves. Further, thermolysis of 13 in refluxing toluene resulted in a clean conversion to 12 within 10 min, N-15-labeled 12 and 13 were syn thesized to establish the structures. These observations provide the f irst example of an interconversion bl:tween an aza- and an aziridinofu lleroid.