Journal of the Chemical Society. Perkin transactions II p. 1225 - 1230 (1988)
Update date:2022-09-26
Topics:
Alcudia, Felipe
Liera, Jose Manuel
Garcia Ruano, Jose L.
Rodriguez, Jesus H.
The synthesis and conformational analysis of cis- and trans-2-methoxy-5-X- oxane, by 13C n.m.r. at low temperature in several solvents, are reported. ΔG° Values in CD2Cl2 of trans-isomers are -0.61 (X, SMe), +1.65 (X, SOMe more polar isomer), +0.57 (X, SOMe less polar isomer), -0.50 (X, SO2Me), and ≥ +1.4 (X, +SMe 2) kcal mol-1, negative values indicating a preference for the diequatorial conformer. In all cis-compounds only one conformation is present. By comparison of these values with those calculated from 2-methoxyoxane and 3-methylthio derivatives of oxane the role played by the anomeric effect on the (oxygen-sulphur)1.2-g interaction can be inferred.
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