A mechanistic study on the reaction of iminothiadiazolines with activated acetylenes: Competitive pathway through hypervalent sulfurane and zwitterion.

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概要

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• The reaction of 3-aryl-5-benzoyl-2-imino-2,3-dihydro-1,3,4-thiadiazoles (<B>6</B>) with dimethyl acetylenedicarboxylate (<B>4b</B>) gave the corresponding thiazole (<B>8</B>) and benzoyl cyanide through sulfurane (<B>B</B>) by 1,3-dipolar cycloaddition and cis- (<B>9</B>) and trans-vinyl (<B>10</B>) compounds through zwitterion (<B>C</B>) by simple addition. Two types of addition reactions competed each other and the ratio of the two [<I>R</I>=<B>B</B>/<B>C</B>] depended solely on the solvent polarity (<I>E</I><SUB>T</SUB>). Dibenzoylacetylene behaved similarly. Several iminothiazolines and iminothiadiazolines reacted with activated acetylenes and the selectivity for the two types of addition reactions for each system was shown to be affected by quite subtle balance of electron-withdrawing ability of each heterocycle.

• 公益社団法人 日本化学会の論文

著者

• Yamamoto Yohsuke

  Department Of Chemistry Graduate School Of Science Hiroshima University

• Akiba Kin-ya

  Department Of Chemistry Faculty Of Science Hiroshima University

• Inamoto Naoki

  Department Of Chemistry Graduate School Of Science The University Of Tokyo

• Arai Shin-ichi

  Department Of Materials Science Tokai University

• Tsuchiya Tohru

  Department of Applied Chemistry, Faculty of Science and Technology, Keio University

• Ochiumi Masahide

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Arai Shin-ichi

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Inamoto Naoki

  Department of Chemistry and Research Centre for Spectrochemistry, Faculty of Science, The University of Tokyo

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