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Abstract
N-Arylnitrilium salts 1 react with nucleophilic alkenes 2 to afford 3,4-dihydroquinolinium salts 3, which can be transformed into the free bases with aqueous sodium hydroxide. Dehydrogenation of the 3,4-dihydroquinolinium salts 3 with 2,3-dichloro-5,6-dicyano-p-benzoquinone furnishes quinolinium salts 7. If the intermediate carbenium ion A formed by electrophilic attack of 1 on the alkene 2 is conjugatively or hyperconjugatively stabilized, instead of 3,4-dihydroquinolinium salts 3 iminium salts 4 resulting from a Houben-Hoesch reaction, or iminium salts 5 arising from a formal ene reaction are formed. For the 3,4-dihydorquinolinium salt 3ac X-ray structural analysis has been carried out.
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