N. Hoffmann, J. Pete
Oct 16, 2001
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0
Influential Citations
10
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ChemInform
Abstract
Synthesis 2001, No. 8, 18 06 2001. Article Identifier: 1437-210X,E;2001,0,08,1236,1242,ftx,en;C20000SS.pdf. © Georg Thieme Verlag Stuttgart · New York ISSN 0039-7881 Abstract: The irradiation of 3-alkenyloxy-5-hydroxybenzoic acid derivatives 1a–d yields highly functionalized alkyloxyenone derivatives when the reaction is carried out in the presence of acid. A higher reactivity is observed for the corresponding 3-alkenyloxy-5hydroxybenzonitrile compounds 7a, b, which also react in neutral reaction media. In the first step of the reaction, a [2+2] photocycloaddition occurs. The following steps, leading to stable final products, need acid catalysis in the case of the substrates 1a–d. The irradiation of the benzonitrile derivative 7b also furnishes the side product 9, which results from a [2+3] photocycloaddition.