Preparation and Stereochemistry of Some Substituted 4-Selenanones and 4-Selenanols

Article abstract of DOI:10.1021/jo01311a015

The preparation of a number of substituted 4-selenanones and four epimeric pairs of 4-selenanols has been described.The configuration and conformation of the 4-selenanones and 4-selenanols were assigned on the basis of IR, 1H NMR, and 13C NMR spectral data, and the selenane ring was shown to be predominantly in the chair form.The dissociation constants of cyanohydrins from six substituted 4-selenanones were measured in 80percent dioxane at 25 deg C, and the results were analyzed in terms of steric parameters in the flattened ring systems.