Photolyses of Ethyl Azidoformate in Cyclic Ethers

N Torimoto, T Shingaki, T Nagai

Index: Torimoto,N. et al. Bulletin of the Chemical Society of Japan, 1976 , vol. 49, p. 2572 - 2578

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Citation Number: 11

Abstract

Ethoxycarbonyl nitrene, generated by the photolysis of ethyl azidoformate (I), were inserted preferentially into the α C–H bonds of cyclic ethers. The α C–H bonds of cyclic ethers were much more reactive than the corresponding C–H bonds of hydrocarbons for the insertion of the nitrene. In addition, the reactions in cyclic ethers with an alkyl group at the α-position gave unsaturated alkoxyurethanes via a cleavage of the ring C–O bond. It was found that ...