Reactions of trifluoromethylsulfenyl chloride with 1,5-cyclooctadiene

The reaction of 1,5-cyclooctadiene with F 3 CSCl at m 80°;C has been examined and found to furnish both di- and tetrasubstituted adducts. Their mass spectra show the presence of the intact cyclooctyl ring. However, photolyis of a solution of 1,5-cyclooctadiene and F 3 CSCl in dry pentane yields addition, isomerization and dimerization as well as free radical products. The rationalization of the formation of the above products along with their mass spectral characterization is described in this communication.