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The Reaction of Psoralens and Related Benzofurans with Singlet Oxygen An Account of Current Research
Author(s) -
Berdahl Donald R.,
Wasserman Harry H.
Publication year - 1983
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198300059
Subject(s) - chemistry , singlet oxygen , dioxetane , furan , photochemistry , singlet state , aryl , alkyl , oxygen , sulfide , organic chemistry , combinatorial chemistry , chemiluminescence , excited state , physics , nuclear physics
Recent work dealing with the role of singlet oxygen in the biological activity of the psoralens has been reviewed. The reaction of singlet oxygen with benzofurans gives products which result from initially formed dioxetanes. Evidence for dioxetane intermediates was obtained from experiments using diphenyl sulfide as a trapping agent. Psoralen derivatives which contain alkyl or aryl groups on the furan double bond react readily with singlet oxygen to give dioxetane cleavage‐type products. Psoralens which lack furan substituents but possess powerful electrondonating groups in the 5‐ and 8‐positions give rise to peroxidic intermediates which are stable only at low temperature.