Photocycloaddition reactions of pyrazinopsoralen with simple olefins

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Direct photolyses of pyrazinopsoralen (PzPs) with excess olefins such as dimethyl fumarate (DMFu), dimethyl maleate (DMMa) and dimethyl ethylidenemalonate (DMEM) gave C-4-photocycloadducts. The photoproducts were determined to be 1:1 C-4-cycloadducts formed through the addition of 4',5'-furan double bond of the excited PzPs to the olefins. The fluorescence of PzPs was quenched by olefins with rate constants on the order of 10(9)-10(10) M-1/s, The appearance of the long-lived fluorescence component implies a singlet exciplex mechanism for the photocycloaddition reaction of PzPs with excess olefins.
Publisher
AMER SOC PHOTOBIOLOGY
Issue Date
1998-01
Language
English
Article Type
Article
Keywords

MONOFUNCTIONAL PSORALEN; 8-METHOXYPSORALEN; PHOTOCHEMISTRY; FUROCOUMARINS; PHOTOREACTION; DNA

Citation

PHOTOCHEMISTRY AND PHOTOBIOLOGY, v.67, no.1, pp.84 - 89

ISSN
0031-8655
DOI
10.1562/0031-8655(1998)067<0084:PROPWS>2.3.CO;2
URI
http://hdl.handle.net/10203/70325
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