On the mechanism of the thermal conversion of cyclopropenyl-substituted oxazolinones to pyridines

A Padwa, LA Cohen, HL Gingrich

文献索引：Padwa, Albert; Cohen, Leslie A.; Gingrich, Henry L. Journal of the American Chemical Society, 1984 , vol. 106, # 4 p. 1065 - 1073

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被引用次数: 8

摘要

Abstract: Thermolysis or photolysis of a sample of a 3-cyclopropenyl-substituted 2H-azirine produced 2-methyl-3, 4, 5, 6-tetraphenylpyridine in high yield. The reaction can best be rationalized by a mechanism involving formation of a nitrile ylide intermediate followed by intramolecular dipolar cycloaddition to give an azabenzvalene, which subsequently rearranges to the pyridine. The thermal chemistry of a series of cyclopropenyl-substituted ...