155620-96-5Relevant articles and documents
Photoinduced Molecular Transformations. Part 143. (2 + 2) Photoaddition of 3-Hydroxy-1-benzopyran-2-one, 3-Benzyloxycarbonyloxy-1-benzopyran-2-one, and their 8-Methoxy Derivatives, with Alkenes and Formation of 1,2-Disubstituted 1,2-Dihydrofurobenzopyran-4-ones by way of ...
Kobayashi, Kazuhiro,Suzuki, Masayoshi,Suginome, Hiroshi
, p. 2837 - 2842 (2007/10/02)
Direct photoaddition of 3-hydroxy-1-benzopyran-2-one with 2,3-dimethylbut-2-ene in tert-butylalcohol gave tetrahydro-2a-hydroxycyclobutabenzopyran-3-one (63percent) arising from a (2 + 2) photoaddition while photoaddition of 3-(benzyloxycarbonyloxy)-1-benzopyran-2-one and its 8-methoxy derivative with cyclopentene gave 65:35 and 40:60 mixtures of cis-cisoid-cis- (65percent) and cis-transoid-cis-photoadducts (75percent).Removal of the protecting groups of these adducts by hydrogenolysis gave corresponding cis-cisoid-cis cyclobutanols (37percent and 24percent, respectively).Similar (2 + 2) photoadditions of the protected 3-hydroxy-1-bezopyran-2-one and its 8-methoxy derivative with cyclohexene gave a mixture of cis-cisoid-cis and cis-transoid-cis adducts, respectively.Removal of the protecting groups from each adduct gave 85:15 and 70:30 mixtures of the cis-cisoid-cis (86percent) and cis-transoid-cis cyclobutanols (70percent).Photolysis of the hypolidites generated in situ from these cyclobutanols induced regioselective β-scissions of the corresponding cyclobutanoxyl radicals to give furobenzopyran-4-ones (20-34percent) together with 4-(trans-2-iodocycloalkyl)-1-benzopyran-2-ones (7-25percent).The pathways leading to the formation of the products arising from the β-scission are discussed.