Bicyclic, boatlike Cope rearrangements. Probe for conformational preference by the nodal carbon atoms

W Von Eggers Doering, CA Troise

Index: Doering, William von Eggers; Troise, Caroline Ann Journal of the American Chemical Society, 1985 , vol. 107, # 20 p. 5739 - 5745

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Citation Number: 11

Abstract

Abstract: 1, 4-Bis (dideuriomethylene) cyclohexane (Ido) and-cycloheptane (2d0) were rearranged thermally to 1, 4-di-methylene-2, 2, 3, 3-tetradeuteriocyclohexane (Id,) and- cycloheptane (2d4), respectively. The Arrhenius parameters for these intramolecular boatlike Cope rearrangements were determined for ldo, log kl=(12.7 f 0.7)-(45 600 f 1800)/8, and for 2do, log k,=(12.0 f 0.4)-(41 900 f 1200)/8. The activation enthalpy was expected to ...