Studies on Photochemical Reactions of Air Pollutants(15)Photoreactivity of Heptachloro-3'-cyclopentenyldioxy Heptachloro-2-cyclopentene Formed by Exposure of Hexachlorocyclopentadiene to Ultraviolet Light in Air

書誌事項

タイトル別名
  • Studies on Photochemical Reactions of Air Pollutants. XV. Photoreactivity of Heptachloro-3'-cyclopentenyldioxy Heptachloro-2-cyclopentene Formed by Exposure of Hexachlorocyclopentadiene to Ultraviolet Light in Air
公開日
2006
DOI
  • 10.1248/cpb.54.338
公開者
公益社団法人 日本薬学会

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説明

Hexachlorocyclopentadiene (HCCP, 1), one of the starting materials in the synthesis of aldrin (3), was found to be able to epoxidize aldrin (3) to give dieldrin (4) when exposed to artificial light at wavelengths longer than 290 nm. In this photochemical reaction, heptachloro-3′-cyclopentenyldioxy heptachloro-2-cyclopentene (2) was isolated as a key intermediate, which appears to be derived from the interaction between the triplet state of photo-excited HCCP (1) and triplet oxygen (3Σg), but not from that between the ground state of HCCP (1) and singlet oxygen (1Δg). The peroxide (2) plays an important role in the formation of dieldrin (4), because it utilized oxygen atom derived from oxygen in air for the epoxidation.

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