The reaction of 1, 2-epithiodecane with acetyl chloride gave a mixture of S- [1- (chloromethyl) nonyl] thioacetate (1) and S- (2-chlorodecyl) thioacetate (2), and a polymer. The ratio of the yields of (1) and (2) was little changed with the reaction conditions such as reaction temperature, reaction time, and kinds of solvents, and it was about 6 : 4. The yields of (1) and (2), however, became higher when polar solvents such as acetone, ethyl methyl ketone, DMF, acetonitrile, acetic anhydride, and acetic acid were used.
The reaction of 1, 2-epithiooctane, 1, 2-epithiododecane, and 1, 2-epithiotetradecane with acetyl chloride gave similar results to the reaction of 1, 2-epithiodecane with acetyl chloride.
The reaction is presumed to be attack of chloride ion of acetyl chloride to 1, 2-epithioalkanes.