engleski

SYNTHESIS AND PHOTOCHEMISTRY OF STILBENYL-SYDNONES

In continuation of our work on heterocyclic compounds and their photochemical induced intramolecular cycloadditions, the new mesoionic compounds trans-3-{;2-[2-(4-methylphenyl)ethenyl]phenyl}; sydnone(1a), trans-3-{;2-[2-phenylethenyl]phenyl}; sydnone(1b) and trans-3-{;2-[2-(4-methylphenyl)ethenyl]phenylmethyl}; sydnone(2) are synthesized. The sydnone ring is a source of nitrile imine, which might react with the neighboring double bond in intramolecular 1, 3-dipolar cycloaddition giving interesting hetero polycyclic compounds. Upon irradiation, 1a and 1b gave amine and quinoline as main products, formed presumably by an elimination of NO and/or CO via radical intermediate. Irradiation of 2 gave two products, with the same molecular weight, which indicates CO2 elimination and formation of nitrile imine, followed by intramolecular cycloaddition. Structure determination and the mechanism of the photochemical reaction will be discussed

sydnones; stilbenes; photochemistry; synthesis

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