Bimanes. 10. Photochemical Rearrangement of 1,5-Diazabicyclo[3.3.0]octa-3,7-diene-2,6-diones (9,10-Dioxa-anti-bimanes)

Hannah Kanety, Hanna Dodiuk, Edward M. Kosower*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

1,5-Diazabicyclo[3.3.0]octa-3,7-diene-2,6-diones (9, 10-dioxa-anti-bimanes) rearrange quantitatively on irradiation in the 320-nm absorption band to isomeric lactones, one from symmetrical bimanes and two from unsymmetrical bimanes (“mixed” bimanes). The quantum yield of lactone is often high and depends upon bimane substitution and solvent viscosity. Fast intersystem crossing (Huppert et al.4), oxygen inhibition of lactone formation, and efficient formation of lactone via a triplet sensitizer implicate the triplet as a key intermediate. The suggested mechanism of lactone formation involves a twisted π-π* triplet.

Original languageEnglish
Pages (from-to)207-213
Number of pages7
JournalJournal of Organic Chemistry
Volume47
Issue number2
DOIs
StatePublished - 1982

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