Photochemical Studies. On the Photofragmentation of Substituted 1, 2-Dihydrophthalic Anhydrides

Benzion Fuchs*, Gad Scharf

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The irradiation-induced transformations of 4, 5-diphenyl-1, 2-dihydrophthalic anhydride (2b) as well as those of the 3, 6-dimethyl-4, 5-diphenyl and 3, 4, 5, 6-tetraphenyl derivatives (2c, d) are elaborated. All undergo photofragmentation, viz., CO + CO2 ejection to give aromatic hydrocarbons, while only 2b also closes electrocyclically to the bicyclo[2.2.0]hex-5-ene product 5. The quantum yields for fragmentation are indicative in this respect. The rearrangement accompanying the fragmentation of 2d to give 1, 2, 3, 5-tetraphenylbenzene (11) was shown to occur via a triplet excited state, populated by benzene sensitization.

Original languageEnglish
Pages (from-to)5395-5398
Number of pages4
JournalJournal of Organic Chemistry
Volume46
Issue number26
DOIs
StatePublished - Dec 1981

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