Conformational analysis. 46. Conformational equilibria in 3-hydroxy-, 3-methoxy-, and 3-acetoxythianes, their sulfoxides and sulfones, and some corresponding 3- …

E Brunet, EL Eliel, WR Kenan Jr

Index: Brunet, Ernesto; Eliel, Ernest L. Journal of Organic Chemistry, 1986 , vol. 51, # 5 p. 677 - 686

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Citation Number: 20

Abstract

Conformational equilibria have been measured, by low-temperature carbon-13 and proton NMR spectroscopy, for 3-hydroxythiane, ita two epimeric sulfoxides, and the corresponding sulfone and their methyl ethers and acetates, as well as the corresponding derivatives of 3- methyl-3-hydroxythiane and their acetates. Of particular note are large solvent and concentration effects on the conformational free energies, AGO,,, especially in cases ...