Photochemically induced single electron transfer reactions of benzils with allylstannane. Direct observation of reactive intermediates by ESR method.

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概要

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• Although the photochemically induced reaction of benzil with allyltrimethylstannane in benzene afforded α-allylbenzoin as a major product, benzil did not react thermally with the same reagent. An ESR observation disclosed that the benzil anion radical ion-paired upon contact with trimethylstannyl cation (BSnMe<SUB>3</SUB>) was generated during irradiation. Its structure was confirmed by the detection of satellite signals arising from tin isotopes. Moreover, a triplet radical pair was also observed during the photolysis of a solid solution containing benzil and allylstannane at 77 K. This reaction proceeded via a single electron transfer from allylstannane to photoexcited benzil, followed by a cleavage of the C–Sn bond of the allyltin cation radical. Ultimately, a radical pair composed of BSnMe<SUB>3</SUB> and the allyl radical was formed and their coupling gave α-allylbenzoin as an isolated product.

• 公益社団法人 日本化学会の論文

著者

• Maruyama Kazuhiro

  Department Of Chemistry Faculty Of Science Kyoto University

• Matano Yoshihiro

  Department Of Chemistry Graduate School Of Science Kyoto University

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