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

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概要

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• 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.

• 1990-12-25

著者

• 木内 文之

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 金子 主税

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 千葉 卓男

  Pharmaceutical Institute, Tohoku University

• 千葉 卓男

  Pharmaceutical Institute Tohoku University

• 高田 芳宏

  Pharmaceutical Institute Tohoku University

• 高田 芳宏

  Pharmaceutical Institute, Tohoku University

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