Additions of Azomethine Ylides to Fullerene C(60) Assisted by a Removable Anchor.
The addition of nitrile oxides to [60]fullerene, leading to isoxazolinofullerenes, can be reversed using reducing agents such as Mo(CO)(6) or DIBALH. Thus, this reaction can be used, in principle, for protection/deprotection of [60]fullerene or for solubilization purposes. The tether-controlled tandem addition of nitrile oxides and azomethine ylides provides mainly cis-1 patterns. The determination of the structure of bisadducts was obtained by NMR spectroscopy with the help of HMQC, HMBC, and NOEDS techniques. The isoxazoline moiety could be removed using Mo(CO)(6) leaving a fulleropyrrolidine derivative.
Da Ros T
Dipartimento di Scienze Ambientali, Università di Venezia, Dorsoduro 2137, 30133 Venezia, Italy.
Prato
M
Lucchini
V