ChemInform Abstract: 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

1992 photochemistry, radiation chemistry, chemoluminescence photochemistry, radiation chemistry, chemoluminescence O 0160 -084Photoinduced 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.-A new type of photocyclization is observed by irradiation of 2-aminonaphthoquinone with vinylarenes. The resulting cyclobutanes undergo photolysis in the presence of HgO and I2 giving angular and/or linear naphthofurans. Electron-donating groups in the aryl unit favor the formation of angular naphthofurans, while an electron-attracting cyano function leads to linear isomers exclusively. -(KOBAYASHI, K.; SASAKI, A.; TAKEUCHI, H.; SUGINOME, H.; J. Chem.