Photochemical behaviour of 3.4-epoxyprecocene-I and related epoxychromans

Ariamala, G. ; Balasubramanian, K. K. (1989) Photochemical behaviour of 3.4-epoxyprecocene-I and related epoxychromans Tetrahedron, 45 (12). pp. 3769-3774. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)89238-3

Abstract

A systematic study of photochemical behaviour of 3,4-epoxyprecocene-I and related epoxychromans was undertaken. Upon irradiation in acetone or cyclohexane, 3,4-epoxyprecocene-I 1̲ was found to undergo photoisomerisation to the corresponding 3-chromanone 2̲. In contrast, the photochemical behaviour of analogous 3,4-dihydro-3,4-epoxy-2H-1-benzopyrans 3 was found to be dependent upon the nature of solvent. Irradiation of 3 in cyclohexene led to photodecarbonylation leading to the formation of 2,3-dihydrobenzofurans 4̲, whereas irradiation in acetone resulted in the formation of chramanones 5̲.

Item Type:Article
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