7, 12-Dihydropleiadenes. I. Free-Energy Barriers to Conformational Inversion1

PT Lansbury, JF Bieron, M Klein

Index: Lansbury,P.T. et al. Journal of the American Chemical Society, 1966 , vol. 88, # 7 p. 1477 - 1482

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Citation Number: 23

Abstract

Abstract: A variety of 7, 12-dihydropleiadenes has been prepared by multistep syntheses from 1, 8-naphthalic anhydride and aryl Grignard reagents. These nonplanar molecules, whose seven-membered rings are “boat shaped,” undergo conformational inversion at rates too fast to permit isolation of enantiomeric or diastereomeric atropisomers. From variable temperature nmr measurements, free energies of interconversion of 13.2-1 5.6 kcal/mole ...