Regio‐ and stereochemistry of the photo‐ring contraction of 4‐pyrones | Zendy

Pavlik James W. | Zendy; Kirincich Steven J. | Zendy; Pires Richard M. | Zendy

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Regio‐ and stereochemistry of the photo‐ring contraction of 4‐pyrones

Author(s) -

Pavlik James W.,

Kirincich Steven J.,

Pires Richard M.

Publication year - 1991

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.5570280264

Subject(s) - chemistry , contraction (grammar) , stereochemistry , ring (chemistry) , organic chemistry , medicine

Irradiation of 2‐ethyl‐3‐methyl‐4‐pyrone 3 in aqueous solution led to the formation of trans ‐4‐ethyl‐5‐methy‐4,5‐dihydroxycyclopent‐2‐enone 4 and trans ‐2‐methyl‐3‐ethyl‐4,5‐dihydroxycyclopent‐2‐enone 5 . In the latter case 1 H nmr analysis confirmed the trans ‐configuration at C 4 and C 5 . These results are consistent with trapping of a photochemically generated oxabicyclohexenyl zwitterion by nucleophilic attack of both sides of the oxyally system along a path anti to the epoxide ring.

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