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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