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

MorenoMañas M. | Zendy; Papell E. | Zendy; Ribas J. | Zendy; Virgili A. | Zendy; Pleixats R. | Zendy

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

Author(s) -

MorenoMañas M.,

Papell E.,

Ribas J.,

Virgili A.,

Pleixats R.

Publication year - 1986

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570230220

Subject(s) - chemistry , piperidine , thiophenol , lactone , pyrone , derivative (finance) , organic chemistry , reactivity (psychology) , stereochemistry , medicine , alternative medicine , pathology , financial economics , economics

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.

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