Tetrahedron

Intramolecular meta photocycloaddition of conformationally restrained 5-phenylpent-1-enes. Part II: Steric and electronic effects caused by 4-mono-and 4- …

HM Barentsen, AB Sieval, J Cornelisse

Index: Barentsen, Helma M.; Sieval, Alex B.; Cornelisse, Jan Tetrahedron, 1995 , vol. 51, # 27 p. 7495 - 7520

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Citation Number: 17

Abstract

The meta photocycloaddition of 4-substituted 5-phenylpent-1-enes, 10–18, has been studied. The monosubstituted derivatives always prefer 2, 6 addition, independent of the size of the substituent. For 2, 6 addition two basic conformations are possible. Disubstituted compounds yield predominantly 1, 3 addition with the sterically more demanding group exo. Except for the methoxymethyl and THF derivative the oxygen is found exo as a result of ...