Diphenylphosphine Oxide: An Alternative to Organotin Hydrides in the Radical Deoxygenation of Alcohols

Various S-methyl dithiocarbonates of tertiary and secondary alcohols are effectively deoxygenated in high isolated yields by treatment with diphenylphosphine oxide and various radical initiators in boiling dioxane. Deoxygenation of S-methyl dithiocarbonate of primary alcohols can be accomplished similarly in boiling xylenes.