Formation Mechanism of Triketo Cage Compounds from Reaction of Phencyclone with Benzoquinones: Cascade Reaction of Intermolecular [4+2]π and Intramolecular [2+2]π Cycloadditions

Koki YAMAGUCHI; Masashi ETO; Kazunobu HARANO

doi:10.1248/cpb.c13-00240

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Formation Mechanism of Triketo Cage Compounds from Reaction of Phencyclone with Benzoquinones: Cascade Reaction of Intermolecular [4+2]π and Intramolecular [2+2]π Cycloadditions

Koki YAMAGUCHI, Masashi ETO, Kazunobu HARANO

著者情報

キーワード: photocycloaddition, cage compound, cyclopentadienone, benzoquinone, PM6 calculation

ジャーナルフリー早期公開

論文ID: c13-00240

DOI https://doi.org/10.1248/cpb.c13-00240

この記事には本公開記事があります。

The final version of this article is now available: Vol. 61 (2013), No. 10

詳細

抄録

The [4+2]π cycloadduct (3aa) of phencyclone (1a) and benzoquinone (2a) readily transformed into the corresponding [2+2]π cycloadduct (4aa) during purification. The structure of the triketo cage compound was determined by single crystal X-ray analysis. The structure-reactivity relationships are discussed based on the PM6-calculated energy profiles for the whole photocycloaddition of the [4+2]π cycloadducts of some cyclopentadienones and benzoquinones.

責任著者(Corresponding author)

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