Unusual photorearrangements of homoconjugated diacylcyclohexa-2,4-dienes

Jakob Oren, Leah Schleifer, Sarah Weinman, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

Abstract

The unprecedented triplet sensitized electrocyclic ring opening of various 3a,7a-diacyl-3a,7a-dihydroindans (3)-(5) to the corresponding cyclononatriene derivatives (7)-(11) is reported, direct irradiation at all absorbing wavelengths of the keto-ester (5) resulting in a diastereoselective oxa-di-π-methane (ODPM) rearrangement to the tricyclic product (6); dimethyl 1,2-dimethyl-1,2-dihydrophthalate (15) reacted similarly to give dimethyl E,E,E-2,7-dimethyl-2,4,6-octatrienoate (16), whose structure has been determined by single crystal X-ray diffraction analysis.

Original languageEnglish
Pages (from-to)315-317
Number of pages3
JournalChemical Communications
Issue number4
DOIs
StatePublished - 1988

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