Isoquinolinium N-arylimides and trans-cyclooctenes

The inertness of isoquinolinium N-arylimides (5a,b) versus common cycloalke nes is overcome by the highly reactive (E)-cyclooctene and (E,Z)-1,5-cycloo ctadiene. NMR spectra and an X-Ray analysis established the retention of di polarophile configuration in the cycloadducts (7a,b) and (9a,b) which were obtained in > 90% yield. Acid-base catalysis effects the opening of the pyr azolidine ring by beta-elimination; the products are 1-[trans-2-arylaminocy clooctyl]isoquinolines (8,10).