Photocycloaddition of arylethenes to 2-substituted-1, 4-naphthoquinones and reactions of the cyclobutane adduct isomers

S Cleridou, C Covell, A Gadhia, A Gilbert…

Index: Cleridou, Stephanie; Covell, Christopher; Gadhia, Anita; Gilbert, Andrew; Kamonnawin, Patcharawalai Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 7 p. 1149 - 1155

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Citation Number: 8

Abstract

The photoreactions of 2-chloro-, 2-bromo-, 2, 3-dichloro-and 2, 3-bromo-1, 4- naphthoquinones with arylethenes are dependent on the addend structure. Cyclobutane adducts are formed from styrene, 1, 1-diphenylethene undergoes photosubstitution to give photolabile 1, 1-diphenyl-1, 3-diene derivatives, and spiro-oxetanes are the main products with trans-stilbene. 2-Acetoxy-1, 4-naphthoquinone undergoes efficient (2π+ 2π) ...