Photolyses of S,S-dimethyl-N-(ethoxycarbonyl)sulfimide in hydrocarbons and in oxygen compounds.

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概要

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• The behavior of ethoxycarbonylnitrene (<B>3</B>), generated photochemically from <I>S</I>,<I>S</I>-dimethyl-<I>N</I>-(ethoxycarbonyl)sulfimide (<B>1</B>), upon insertion into the C–H bonds and the O–H bonds was compared with that of <B>3</B> generated from ethyl azidoformate (<B>2</B>). Ethoxycarbonylnitrene generated from <B>1</B> was inserted preferentially into the α C–H bonds of cyclic ethers. The relative reactivity toward <B>3</B> of the primary, secondary, and tertiary C–H bonds in 2,4-dimethylpentane is in the ratio of 1 : 9 : 35. The insertion of <B>3</B> into the tertiary C–H bonds of <I>cis</I>- and <I>trans</I>-1,4-dimethylcyclohexanes proceeded stereospecifically. The reaction of <B>3</B> with alcohols gave the O–H insertion products. These results show that the insertion of <B>3</B> generated from <B>1</B>, as well as that of the nitrene from <B>2</B>, into the hydrocarbon C–H bo nds and the O–H bonds proceeds only for the singlet.

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.
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• 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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