4??Hydroxy??6??methyl??2??pyrone (triacetic acid lactone) and its 3??phenylthiomethyl derivative towards aldehydes in the presence of piperidine

…, E Papell, J Ribas, A Virgili, R Pleixats

Index: Moreno-Manas, M.; Papell, E.; Pleixats, R.; Ribas, J.; Virgili, A. Journal of Heterocyclic Chemistry, 1986 , vol. 23, p. 413 - 416

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Citation Number: 11

Abstract

Abstract Aldehydes react with triacetic acid lactone, 1, in the presence of piperidine to afford the pyrones 3a-d and 5. The intermediacy of quinone-methides of type 2a-e has been postulated, and experimental evidence for their existence has been achieved by generation by thiophenol elimination from 7 and subsequent trapping in Diels-Alder reactions. Two examples are given in reactivity of 7 at the sluggish C-5 position.