Reactions de photoaddition de benzo[b]selenophenes avec l'acetylene dicarboxylate de methyle et avec le dichloro-1,2 ethylene |
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Authors: | Tran Quang Minh Léon Christiaens Pierre Grandclaudon Alain Lablache-Combier |
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Institution: | Laboratoire de Chimie Organique Hétérocyclique, Institut de Chimie, Université de Liège, Sart-Tilman par 4000 Liège-1, Belgique;Laboratoire de Chimie Organique Physique, Université des Sciences et Techniques de Lille B.P. 36, 59650-Villeneuve d''Ascq, France |
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Abstract: | Photoirradiated in presence of acetophenone, benzob]selenophene and its 3-methyl derivative add to dimethyl acetylenedicarboxylate. In each ease, the primary reaction product is unstable and has not been isolated. Photoexeited in its triplet state (the energy of which is in the neighbourhood of 69 ) benzob]selenophene and its 2- and 3-methyl, 2,3 dimethyl, 3 acetoxy and 2-methyl-3-acetoxy derivatives add to 1,2 dichloroethylene leading to cyclobutanes. Neither cyclo-addition occurs in absence of photosensitiser. Single-crystal X-ray analysis gave the structures of the two adducts of 3-acetoxybenzob]selenophene with trans-1,2-dichloroethylene. In both compounds the chlorine atoms are trans. |
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