Tetrahedron letters

The remarkable configurational stability of ortho, ortho′-tetrafluoro substituted biphenyls: 2, 2′, 4, 4′, 6, 6′-hexafluorobiphenyl-3, 3′-dicarboxylic acid as a model

F Leroux, M Maurin, N Nicod, R Scopelliti

Index: Leroux, Frederic; Maurin, Michael; Nicod, Nathalie; Scopelliti, Rosario Tetrahedron Letters, 2004 , vol. 45, # 9 p. 1899 - 1902

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Citation Number: 16

Abstract

Optically active 2, 2′, 4, 4′, 6, 6′-hexafluorobiphenyl-3, 3′-dicarboxylic acid was obtained through its brucine salt. The half-life time for racemization was determined at various temperatures and the torsional barrier for racemization was calculated to be 25.4 kcal/mol. These results prove, contrary to textbook knowledge, that ortho, ortho′-tetrafluoro substituted biphenyls are resolvable.