Reactions of β-azidostyrenes with halogenoacetic acid. A novel formation of oxazoles

H Takeuchi, Y Kitamura, S Hayakawa…

Index: Takeuchi, Hiroshi; Kitamura, Yasunori; Hayakawa, Satoshi; Koyama, Kikuhiko Journal of the Chemical Society, Chemical Communications, 1989 , # 19 p. 1414 - 1415

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Abstract

The reaction of 0-azidostyrene with trifluoro-, trichloro-, dichloro-, or monochloro-acetic acid gave 2-halogenomethyl-5-phenyloxazole via attack of halogenoacetate anion on a benzylic carbocation or a conjugate acid of the azide. ... The thermal reaction of P-azidostyrene is known to give phenylacetonitrile together with indole via a vinylnitrene. 1 We have reported that phenylnitrenium ion generated from phenyl azide in the presence of trifluoroacetic acid (TFA) gives rise to an ...