Journal of the Chemical Society. Perkin transactions II p. 175 - 184 (1981)
Update date:2022-08-16
Topics:
Craze, Gabrielle-Anne
Watt, Ian
The hydroxyketones (1) and (2) have been prepared from the Diels-Alder adducts of p-benzoquinone with cyclopentadiene and cyclohexa-1,3-diene.The boron trifluoride-ether catalysed reaction of cyclohepta-1,3-diene with p-benzoquinone gave good yields of the Diels-Alder adduct which was converted into hydroxyketone (3).Experiments with cyclohexanol and admantan-2-ol established characteristic 13C n.m.r. chemical shifts associated with deprotonation of alcohols by dimsyl sodium in dimethyl sulphoxide.Solutions of the sodium salts of (1)-(3) were prepared and dynamic 13C n.m.r. spectroscopy gave barriers for their degenerate rearrangement of >21.7 (100 deg C), 19.0 (100 deg C), and 17.3 (72 deg C) kcal mol-1, respectively.The relationship between variation of barrier and molecular geometry is discussed with the aid of empirical force field calculations.
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