Photolysis of Ethyl Azidoformate in Ethers and in Alcohols

N Torimoto, T Shingaki, T Nagai

Index: Torimoto,N. et al. Bulletin of the Chemical Society of Japan, 1977 , vol. 50, p. 1517 - 1521

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Citation Number: 7

Abstract

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 N-alkoxyurethane via 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– ...