Photoinduced molecular transformations. Part 127. A new [2 + 2] photoaddition of 2-amino-1,4-naphthoquinone with vinylarenes and the synthesis of 2,3-dihydronaphtho[1,2-b]furan-4,5-diones and 2,3-dihydronaphtho[2,3-b]furan-4,9-diones by β-scission of alkoxyl radicals generated from the resulting photoadducts

Abstract

Photoinduced Molecular Transformations. Part 127." A New [2 + 21 Photoaddition of 2-Amino-I ,4-naphthoquinone with Vinylarenes and the Synthesis of 2,3-Di hydronaphtho[l,2-b]f uran-4,5-diones and 2,3-

The Application of Cyclobutane Derivatives in Organic Synthesis

“…Exclusive 4,5-dione formation was obtained for p -methoxyphenyl (70% yield), whereas a p -cyanophenyl-substituted system gave the 4,9-dione (40%). On the other hand, the 4,9-dione 356 underwent isomerization to the 4,5-dione 354 on silica gel 123 …”

“…In comparison to the photolytic ring cleavage of tertiary cyclobutanols fused to an ortho -naphthoquinone, which led to tetrahydrofurans, the photoadducts of enolized tetralones with either methyl acrylate or acrylonitrile gave benzoannelated eight-membered ring derivatives . The cyclobutanol 555 gave the bifunctional benzocyclooctadienone 556 in 47% yield upon treatment with HgO/I 2 under irradiation conditions.…”