5-Butynylisoxazoles were obtained in high yields through a domino addition, C–O heterocyclization involving allenylmagnesium bromide and benzonitrile oxide in dry THF, in which the corresponding 5-methylisoxazoles were isolated in trace amounts. However, when the reactions were attempted in aqueous media using allenylindium bromide, 5- methylisoxazoles were formed as the sole products in high yields.
[Akhtar, M. Shamim; Seth, M.; Bhaduri, A. P. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, p. 71 - 72]