Synfacts 2007(3): 0265-0265  
DOI: 10.1055/s-2007-968211
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Regioselective Multiple Additions to C60

Contributor(s): Timothy M. Swager, Eric L. Dane
S.-C. Chuang, S. I. Khan, Y. Rubin*
University of California, Los Angeles, USA
Further Information

Publication History

Publication Date:
20 February 2007 (online)

Significance

A temporary directing group, which sterically hinders and electronically alters the preferred substitution sites of C60, is used to regio­selectively substitute C60 at three of the trans-4 positions to form a C 3v -symmetric molecule. The directing group is attached to C60 via a Diels-Alder reaction and the Bingel reaction is then used to add cyclopropane adducts. The authors found that dimethylanthracene was required as a templating agent. The directing group is removed from the substituted product by heating in the prescence of a great excess of C60.