REISSERT COMPOUND STUDIES .64. REISSERT COMPOUND AND OTHER PRODUCTS FROM AN ISOLATED N-BENZOYLISOQUINOLINIUM TRIFLATE SALT

In the presence of trimethylsilyl trifluoromethanesulfonate, a methylene chloride solution of isoquinoline and benzoyl chloride gave N-benzoylisoquinolinium triflate (3) and N-H-isoquinolinium triflate (4). Depending on the reaction conditions, reaction of 3 may occur on the isoquinoline ring yielding a Reissert compound and 1,2-dihydroisoquinoline species. Otherwise, reactions transpire on the carbonyl of 3 to give an amide, an ester, and an anhydride.