Tetrahedron

Aromatization reactions of 4-hydroxy-6-phenacyl-2-pyrone and related compounds

TM Harris, MP Wachter

Index: Harris,T.M.; Wachter,M.P. Tetrahedron, 1970 , vol. 26, p. 5255 - 5263

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Citation Number: 8

Abstract

Treatment of the title compound with various acidic and basic reagents brought about cleavage of the lactone ring to form unstable intermediates which recyclized in several manners. With strong acids the compound was transformed to γ-pyrones, with nucleophilic bases to resorcinols, and with non-nucleophilic bases to benzoylphloroglucinol. In the first two reactions the corresponding 3, 5, 7-triketo acid or ester is an intermediate. The use of ...

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