Reissert compound studies. LXIV. 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.