Gurvinder Gill - Interconversion of Carbon Sites in Boat-Chair-Boat Cyclodecane and Conformations of Monosubstituted Cyclodecanes.

Version 1

      Publication Details (including relevant citation   information):

      Pawar, D., Davis, D., Gill, G., Bain, A., Sullivan, R., and Noe,   E. (2007). Journal of Organic Chemistry, 72,   25-29.

      Abstract:

      Interconversion   of carbon sites in boat-chair-boat (BCB) cyclodecane occurs by   way of the twist-boatchair

      (TBC)   conformation, which predicts that C-1 exchanges with C-4, etc.   The previously obtained low-temperature 13C   spectra could be matched by assuming (1,4) or (1,3) exchange, but   not (1,2) exchange. A free-energy   barrier of 5.54 kcal/mol was obtained for conversion of BCB to   TBC at -137.4  °C.   The major   conformation of chlorocyclodecane and cyclodecyl acetate is   assigned to the IIIe BCB.

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