A new method for the deoxygenation of secondary alcohols

On reaction with tributylstannane, O-cycloalkyl thiobenzoates and O-cycloalkyl S-methyl dithiocarbonates, derived from secondary alcohols, give good yields of the corresponding hydrocarbons. The mechanism of this planned reaction is radical in character and thus rearrangements common in carbocation reactions are avoided. The particular applicability of this procedure in sugar chemistry is illustrated. The reaction takes place under neutral conditions compatible with the presence of the functional groups which normally occur in aminoglycoside antibiotics.