Tetrahedron

Heterocyclic steroids—VII: Rearrangement of 1-diethylamino-5-(m-methoxyphenoxy)-pent-2-yne

TR Kasturi, G Govindan, KM Damodaran…

Index: Kasturi,T.R. et al. Tetrahedron, 1973 , vol. 29, p. 715 - 718

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Abstract

Thermal rearrangement of diethylamino-5-(m-methoxyphenoxy)-pent-2-yne (3) gives 1-(m- methexyphenoxy)-pent-3, 4-diene (14) in about 8% yield. Hydration of the latter yields 1-(m- methoxyphenoxy)-pentan-4-one (6), which has been synthesised by an unambiguous route. A mechanism of formation of the allene (14) from the amine (3) has been suggested.

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