A new method for the functionalization of [60] fullerene: an unusual 1,3-dipolar cycloaddition pathway leading to a C60 housane derivative.

[reaction: see text] A variant of the Huisgen 1,3-dipolar cycloaddition reaction provides a new and convenient functionalization of fullerenes. This method complements the widely used Prato and Bingel-Hirsch reactions. The derived, highly functionalized cyclopentenone and cyclopentenamine fullerene compounds upon hydrolysis are suitable for further functionalization and may serve well in the synthesis of new C60 derivatives possessing uncommon and interesting properties.