Photolysis of ethyl azidoformate in ethers and in alcohols.

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概要

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• Ethoxycarbonyl nitrene, generated by the photolysis of ethyl azidoformate (I), was inserted preferentially into the α C–H bonds of acyclic ethers. Each of the reactions with acyclic ethers gave <I>N</I>-alkoxyurethane <I>via</I> a cleavage of the C–O bond, indicating that an O–N ylide is an intermediate of the nitrene reaction. Comparing sensitized photolysis with direct photolysis of I in ethers and in alcohols, it was found that the nitrene insertion into the α C–H bonds of ethers proceeds for both singlet and triplet and that the insertion into the β and γ C–H bonds of ethers and the O–H bonds of alcohols proceeds only for the singlet.

• 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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