Gurvinder Gill - Interconversion of Carbon Sites in Boat-Chair-Boat Cyclodecane; Conformations of Chlorocyclodecane and Cyclodecyl Acetate

Version 1

      Publication Details (including relevant citation   information):

      J. Org. Chem, Vol. 72, No. 1, 2007 29


      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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