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Intramolecular [2+2] Photocycloaddition of Bichromophoric Derivatives of 3,5-Dihydroxybenzoic Acid and 3,5-Dihydroxybenzonitrile
Ist Teil von
Synthesis (Stuttgart), 2001-01, Vol.112 (8)
Erscheinungsjahr
2001
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
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-5-hydroxybenzonitrile 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.