Copper-initiated decomposition of N,N-dichloromethanesulfonamide.

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概要

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• The reactions of <I>N</I>,<I>N</I>-dichloromethanesulfonamide (I) with substrates such as hydrocarbons and ethers gave the <I>N</I>-substituted methanesulfonamide (II) and methanesulfonamide (III) in the presence of copper. The reaction with 2-methylbutane gave the product only with a tertiary C–H bond, though the singlet nitrene which was generated from methanesulfonyl azide reacted with the primary, secondary, and tertiary C–H bonds in the ratio of 1 : 4.2 : 9.6. The reactions with the tertiary C–H bonds of <I>cis</I>- and <I>trans</I>-1,4-dimethylcyclohexanes proceeded non-stereospecifically, in contrast to those of the nitrene with them. The addition of a radical inhibitor, hydroquinone, reduced the yield of II, while it increased the yield of III. The reaction with alcohols led to a quantitative yield of III, accompanied by the corresponding aldehydes. These results suggest that the reaction proceeds not by a nitrene mechanism, but by a metal-radical mechanism.

• 公益社団法人 日本化学会の論文

著者

• Shingaki Tadao

  College of General Education, Osaka University

• Nagai Toshikazu

  College of General Education, Osaka University

• Torimoto Noboru

  Science Education Institute of Osaka Prefecture

関連論文

• Photolyses of S,S-dimethyl-N-(ethoxycarbonyl)sulfimide in hydrocarbons and in oxygen compounds.
• Copper-initiated decomposition of N,N-dichloromethanesulfonamide.
• The decomposition of N,N-dichlorourethane by copper: A comparison with the photolysis of ethyl azidoformate.
• Photolysis of ethyl azidoformate in ethers and in alcohols.
• Photolyses of ethyl azidoformate in cyclic ethers.
• On the behavior of sulfonyl imide as a reactive intermediate. The reaction with enamines.

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