Studies on the Conformation of Some Substituted 4-Selenanols

Article abstract of DOI:10.1021/jo00325a021

The second-order rate constants for acetylation with acetic anhydride in pyridine have been measured at 40 deg C for seven pairs of epimeric 4-selenanols, and the conformations of these compounds were determined from the kinetic data. 1H NMR and 13C NMR spectra were also recorded and analyzed.The 1H chemical shift of the carbinol protons and 13C chemical shift of the carbinol carbons are analyzed in the light of previously established correlations.Carbon-13 chemical shift data suggest that 2,2-dimethyl-trans-6-(p-chlorophenyl)selenan-r-4-ol exists in a nonchair conformation.