Excited State Carbon Acids: Base Catalysed Photoketonization of Dibenzosuberenol to Dibenzosuberone via Initial C-H Bond Heterolysis from S1

DOI: 10.1039/c39900000255

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 255 - 257 (1990)

Update date:2022-08-11

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Authors:

Wan, Peter

Budac, David

Krogh, Erik

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Article abstract of DOI:10.1039/c39900000255

A new photoreaction, the photoketonization of dibenzosuberenol (1) to dibenzosuberone (2) in aqueous solution, is reported, the mechanism of which is believed to involve initial ionization of the C-H proton at the 5-position (in S₁), to generate a 5-hydroxy-5-dibenzosuberenyl (9) carbanion intermediate.

Full text of DOI:10.1039/c39900000255

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