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Synfacts 2006(7): 0666-0666
DOI: 10.1055/s-2006-941873
DOI: 10.1055/s-2006-941873
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York
An Orthogonal Protection-Deprotection Route to Antipodal Fullerene Derivatives
S. Zhang, O. Lukoyanova, L. Echegoyen*
Clemson University, USA
Further Information
Publication History
Publication Date:
22 June 2006 (online)
Significance
The antipodal bisadduct of anthracene and [60]fullerene - itself obtained in exceptional yield and selectivity from a topochemical disproportionation of the readily available monoanthracene adduct - is among the few antipodal fullerene adducts that can be obtained efficiently and selectively in large quantities. A series of selective protection (cyclopropanation) and deprotection (retro-Diels-Alder, retro-cyclopropanation) steps translate the initial regioisomer into functionalized trans-1 bispyrrolidinofullerenes.