Surprises, Serendipity, and Symmetry in Fullerene Chemistry

Abstract

Fullerene chemistry studies often reveal unexpected phenomena, produce the occasional success, and require greater familiarity with symmetry than is customary in organic chemistry. These aspects are encountered in our studies of the formation of fullerene hydrides, hydroxides, halides, oxides, arylfullerenes, and cycloadducts.

Water-Promoted Reaction of C60Ar5Cl Compounds with Thiophenes Delivers a Family of Multifunctional Fullerene Derivatives with Selective Antiviral Properties

“…The elimination of chloride in the form of HCl generates unstable antiaromatic cation on the fullerene cage. It is known that such a cation readily undergoes a 1,2-shift of one of the addends, 19,20 which results in the formation of the more stable allylic carbocation. The allylic carbocation then attacks the thiophene in the most reactive and less sterically hindered position.…”