Stereodynamics and edge-to-face CH-π aromatic interactions in o-phenethyl-substituted biaryls

WB Jennings, BM Farrell, JF Malone

Index: Jennings, W. Brian; Farrell, Brid M.; Malone, John F. Journal of Organic Chemistry, 2006 , vol. 71, # 6 p. 2277 - 2282

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Citation Number: 27

Abstract

As part of a search for systems that exhibit intramolecular aromatic edge-to-face interactions, a series of four biaryl compounds containing a phenethyl side chain were prepared. These compounds exist as a slowly interconverting mixture of two atropisomers due to steric hindrance to rotation about the biaryl bond. The more thermodynamically stable isomer exhibits an abnormal shielding of an ortho-proton in solution indicative of an edge-to-face ...