Synfacts 2006(04): 0339-0339  
DOI: 10.1055/s-2006-932064
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Amino Acid Ester and Carbon Disulfide C60 Functionalization

Contributor(s): Timothy Swager, Scott Meek
J. Li, Y. Li, Y. Liu, G. Wang*
University of Science and Technology of China, Hefei and Lanzhou University, P. R. China
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Publikationsverlauf

Publikationsdatum:
24. März 2006 (online)

Significance

A novel method for the functionalization of C60 with amino acid esters and CS2 is reported. The technique involves stirring the hydrochloride salt of the amino acid ester with C60 in CS2 at room temperature with excess Et3N. Four amino acid esters were tested (1a-d) with major product (2a-d) yields ranging between 30% and 40% and minor product yields (3a-d) between 0% and 6%. The reaction is proposed to proceed through isothiocyanate anion intermediates 5a-d which cyclize with the fullerene and are then either protonated to form the major product or attack 4a-d to form the minor product.