Allylamines, readily accessible by ene reactions of N,N-dibenzyliminium pentachlorostannates with 1,3-enynes, undergo domino reactions with maleic anhydride or maleic imide to give cisfused hexahydroisoindolones, which were characterized by x-ray analysis.
The iminium salt Bn 2 N + =CH 2 SnCl 5 -undergoes ene reactions with inverse electron demand with alkynes and with the triple bond of enynes to give benzylideneammonium ions in aprotic solvents. Their hydrolysis yields N-benzylallylamines in good yields. Mannich reaction products, which are the main products under more nucleophilic reaction conditions, have not been detected.
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