Photoaddition of ethenes to 1,4-naphthoquinone: factors influencing the site of reaction

Autor:	Derek Bryce-Smith, Andrew Gilbert, Hilary S. McNeill, Elizabeth H. Evans
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Addition reaction chemistry.chemical_compound Electron transfer chemistry Alkene Moiety Electron donor Electron acceptor Photochemistry Quinone Cyclobutane
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :485
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19920000485
Popis:	1,4-Naphthoquinone undergoes photocycloaddition to a variety of electron donor and electron acceptor ethenes giving spirooxetanes and/or cyclobutane derivatives. The site of addition onto the quinone depends on the electron donor character of the ethene, with the spirooxetane being generally favoured with ethenes of low oxidation potential. 2,3-Dimethylbut-2-ene, the strongest electron donor ethene studied, also gave a novel acyclic addition product involving the ethene moiety of the quinone. The two types of 1,4-naphthoquinone cycloadducts have appreciable in vitro cytotoxicity.
Databáze:	OpenAIRE
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