3,3,6-Trimethyl-2-chlorocyclohexeno[1,2-d]-1,2-oxaphosphol-4-ene-2-oxide as a convenient precursor for the synthesis of dimephosphone analogs


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Abstract

A convenient approach to the synthesis of 3,3,6-trimethyl-2-chlorocyclohexeno[1,2-d]-1,2-oxaphosphol-3-ene-2-oxide was developed based on the reaction of the naturally occurring terpenoketone pulegone with methyl dichlorophosphite. Treatment of oxaphospholene-2-oxide with water or ethanol yielded γ-phosphoryl ketones, dimephosphone analogs. The studied hydrolysis and alcoholysis processes differ in stereoselectivity.

About the authors

A. V. Nemtarev

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center; Kazan Federal University

Author for correspondence.
Email: a.nemtarev@mail.ru
Russian Federation, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088; Kazan, Tatarstan

M. E. Shemakhina

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center; Kazan Federal University

Email: a.nemtarev@mail.ru
Russian Federation, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088; Kazan, Tatarstan

V. F. Mironov

Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center; Kazan Federal University

Email: a.nemtarev@mail.ru
Russian Federation, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088; Kazan, Tatarstan


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