ON THE REACTION OF 1,3-DICHLORO-2-AZONIAALLENE SALTS WITH OLEFINS ANDDIPHENYLACETYLENE

1,3-Diaryl-1,3-dichloro-2-azoniaallene salts 1 react with di-, tri- an d tetraalkyl and aryl substituted olefins to form new types of 2-azoni aallene salts 4, a 4-azapentadienyl salt 5e or pyridinium salts 8, res pectively. The cycloaddition of olefins to 1,3-dichloro substituted 2- azoniaallene ions proceeds stepwise via carbocations. An X-ray structu ral analysis of the cycloadduct of 1 with norbornene is presented. Wit h diphenylacetylene, compounds 1 react to give 11 H-indeno[1,2-c]isoqu inolinium salts 12. The free bases are generated from the hexachloroan timonates by treatment with aqueous sodium hydroxide or sodium hydroge n carbonate.