(2+4) and (6+4) Type cycloaddition reactions of 1-ethoxycarbonyl-1H-azepine and 1-ethoxycarbonyl-1H-1,2-diazepine with 3,4,5,6-tetrachloro-1,2-benzoquinone.

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概要

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• The reaction of 1-ethoxycarbonyl-1<I>H</I>-azepine with 3,4,5,6-tetrachloro-1,2-benzoquinone at room temperature gave a [6+4]-type cycloadduct as the major product and two kinds of [2+4]-type cycloadducts. In this reaction the diketone moiety of the benzoquinone derivative was used as the 4π component to form ether linkages. The [6+4]-type cycloadduct became rearranged to one of the [2+4]-type cycloadducts by heating at 90 °C. The same reaction, but using 1-ethoxycarbonyl-1<I>H</I>-1,2-diazepine, afforded two kinds of [2+4]-type cycloadducts. An electronic attraction between the oxygen atoms of the benzoquinone derivative and the carbons in the 2 and 7-positions of the azepine derivative is considered to be one of the driving force of the [6+4]-type cycloaddition reaction. The [2+4]-type cycloadducts are regarded to be formed via inverse electron demand Diels–Alder reactions.

• 公益社団法人 日本化学会の論文

著者

• Saito Katsuhiro

  Department Of Agricultural And Resource Economics The University Of Tokyo

• Mukai Toshio

  Department of Chemistry, Faculty of Science, Tohoku University

• Iida Shigenori

  Department of Chemistry, Faculty of Science, Tohoku University

• Mukai Toshio

  Department of Chemistry, Faculty of Science Tohoku University

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