Some New 3-Substituted 3-Hydroxyselenetanes and Their Loss of Selenium

Article abstract of DOI:10.1021/jo00239a019

3-Phenyl,-3-(p-methoxyphenyl)-,and 3-ethyl-3-hydroxyselenetane were prepared by treatment of 2-substituted 2-(chloromethyl)oxiranes with selenide ion at room temperature or lower.At elevated temperatures 2-substituted allyl alcohols were the major products.Treatment of 3-phenyl-3-hydroxyselenetane with base gave 2-phenyl-2-propenol, and attemps to prepare the benzoate and 3,5-dinitrobenzoate of 3-phenyl-3-hydroxyselenetane resulted in the formation of the benzoates of 2-phenyl-2-propenol.The acetate and 3,5-dinitrobenzoate of 3-hydroxyselenetane could be prepared, but they decompose on the attempted purification.NMR evidence is obtained for the formation of 3-selenetanone by oxidation of oxidation of 3-hydroxyselenetane with the Dess-Martin periodinane.An explantion is advanced for the differences in behavior of sulfide, selenide, and telluride ion toward (chloromethyl)oxiranes.An attempt to prepare 3-hydroxytelluretane from 1,3-dibromo-2-propanol and telluride ion gave only isopropyl alcohol.