Issue 0, 1972

Photoconversion of 2,6-bis(alkylthio)-3,5-diphenyl-4H-thiopyran-4-ones into 3,4-bis(alkylthio)-2,5-diphenylcyclopentadienones

Abstract

The irradiation of 2,6-bis(alkylthio)-3,5-diphenyl-4H-thiopyran-4-ones (2) with a medium-pressure mercury arc lamp through a Pyrex filter produced 3,4-bis(alkylthio)-2,5-diphenylcyclopentadienones. The quantum efficiency for formation of cyclopentadienone derivatives was very low (Φ= 0·0002). Sensitization and quenching studies indicate that the reaction involves the triplet state of compounds (2). Cycloadditions of the photoproduct with some dienophiles were studied. The mechanism of the photochemical rearrangement of compounds (2) is discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 1203-1208

Photoconversion of 2,6-bis(alkylthio)-3,5-diphenyl-4H-thiopyran-4-ones into 3,4-bis(alkylthio)-2,5-diphenylcyclopentadienones

N. Ishibe, M. Odani and R. Tanuma, J. Chem. Soc., Perkin Trans. 1, 1972, 1203 DOI: 10.1039/P19720001203

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