Diels-Alder adduct of C60 and 4-carboxy-o-quinodimethane: synthesis and chemical transformations

P Belik, A Guegel, A Kraus, M Walter…

Index: Belik, Pavel; Guegel, Andreas; Kraus, Alexander; Walter, Michael; Muellen, Klaus Journal of Organic Chemistry, 1995 , vol. 60, # 11 p. 3307 - 3310

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Citation Number: 73

Abstract

The Diels-Alder reaction of o-quinodimethanes to buckminsterfullerene c60 (1) affords thermally stable derivatives. 4-Carboxy-o-quinodimethane (4) was prepared in situ from 3, 4- bis (bromomethyl)-benzoic acid (3) and reacted with 1 to give the carboxy-substituted adduct mixture 5 (n). Due to its decreased solubility, 5 (n) was used without further purification for transformations into the corresponding esters and amines. This was achieved by two ...