Author:
Cox A.,Kemp D. R.,Lapouyade R.,Mayo P. de,Joussot-Dubien J.,Bonneau R.
Abstract
A number of polycyclic aromatic thiones have been prepared from the corresponding ketones. Several of the thiones in which there is a free peri position cyclize, on excitation in the π* ← n band, to give thiophene derivatives. The structures of these were proven by application of physical methods and by desulfurization to the corresponding benzyl derivatives. The formal hydrogen 1,3 migration involved was, in one case, shown to be intermolecular by the incorporation of deuterium, from deuterium oxide, during the irradiation. In the case of the α-naphthyl derivative, the mechanism of the reaction has been investigated and it has been concluded that the n,π* singlet is the responsible entity.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
17 articles.
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