Cycloadditions in Syntheses. LII. Stereochemical Pathways of 1-Isoquinolone-Chloroethylene Photo [2 + 2] cycloaddition: Determination of Regio- and Stereostructures of the Products and Explanation for Their Formation

Takuo Chiba, Yoshihiro Takada, Chikara Kaneko, Fumiyuki Kiuchi, Yoshisuke Tsuda

研究成果: Article査読

15 被引用数 (Scopus)

抄録

The cycloaddition of isoquinolone and its N-methyl derivative to all the chlorinated ethylenes has been studied. The structures of all of the photoadducts were determined on the basis of X-ray crystallographic analysis as well as nuclear magnetic resonance spectroscopy and it was found that the cyclobutane rings in the adducts took puckered conformation. The details of the two-step closure process via biradical intermediates are discussed and it is concluded that σ-bond rotation prior to spin relaxation in the biradical intermediates takes a primary role in determination of the stereochemical outcome. The interesting fact that more trans products are formed from cis-dichloroethylene and more cis products from trans-dichloroethylene can also be explained in terms of the present proposal.

本文言語English
ページ(範囲)3317-3325
ページ数9
ジャーナルChemical and Pharmaceutical Bulletin
38
12
DOI
出版ステータスPublished - 1990 1月 1
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

フィンガープリント

「Cycloadditions in Syntheses. LII. Stereochemical Pathways of 1-Isoquinolone-Chloroethylene Photo [2 + 2] cycloaddition: Determination of Regio- and Stereostructures of the Products and Explanation for Their Formation」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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