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

Kasturi, T. R. ; Govindan, G. ; Damodaran, K. M. ; Subrahmanyam, G. (1973) Heterocyclic steroids-VII: rearrangement of 1-diethylamino-5-(m-methoxyphenoxy)-pent-2-yne Tetrahedron, 29 (5). pp. 715-718. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(73)80083-3

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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