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Intramolecular photoreactions of 6‐(ω‐alkenyl)‐4‐methoxy‐2‐pyrones
Author(s) -
Shimo Tetsuro,
Matsuzaki Shigeki,
Somekawa Kenichi
Publication year - 1994
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.5570310222
Subject(s) - chemistry , intramolecular force , tricyclic , adduct , stereochemistry , intramolecular reaction , medicinal chemistry , organic chemistry
6‐(ω‐Alkenyl)‐2‐pyrones 3a‐c and 8a, b were prepared and the photochemical reactions were investigated. Photosensitized reactions of 3b, c gave intramolecular [2+2]‐cycloadducts 11b, c as tricyclic lactones, site‐and regio‐specifically. They are not frontier‐orbital‐controlled adducts. On the other hand, 3a, 8a, b afforded cyclobutenecarboxylic acids, 10a, 14a, b , respectively. The end‐ester group at the side‐chain is thought not to be effective for the intramolecular phptoaddition.