The Journal of Organic Chemistry

Intramolecular photochemical reactions of bichromophoric 3-(alkenyloxy) phenols and 1-(alkenyloxy)-3-(alkyloxy) benzene derivatives. Acid-catalyzed transformations …

N Hoffmann, JP Pete

Index: Hoffmann, Norbert; Pete, Jean-Pierre Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6952 - 6960

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Citation Number: 27

Abstract

Irradiation of 3-(alkenyloxy) phenols and 1-(alkenyloxy)-3-(alkyloxy) benzene derivatives, at λ= 254 nm in acidic media, yields benzocyclobutenes, 3-alkylphenols, 3-alkylanisols, and 4- alkyl-1, 2-dialkyloxybenzenes depending on the substitution pattern of the aromatic ring and the olefinic side chain. The final products are derived from an intramolecular [2+ 2] photocycloaddition and acidic rearrangements from a common intermediate.

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