Volume 28, Issue 3 e21366
RESEARCH ARTICLE
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Novel O-alkyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridates: Synthesis and properties

Elmira M. Gibadullina

Elmira M. Gibadullina

A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

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Ramilya R. Azmukhanova

Corresponding Author

Ramilya R. Azmukhanova

A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

Correspondence

Ramilya R. Azmukhanova, A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia.

Email: [email protected]

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Michael A. Pudovik

Michael A. Pudovik

A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

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Alexander R. Burilov

Alexander R. Burilov

A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

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First published: 21 February 2017
Citations: 1
Contract grant sponsor: Russian Foundation for Basic Research.
Contract grant number: 15-03-01046-a.

Abstract

The reaction of O,O-dialkyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonates with phosphorus pentachloride affords O-alkyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridates. A transformation of O-alkyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridates into diphosphonates is discovered. Base-mediated reactions of methyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridates with aliphatic alcohols are studied. The reaction of alkyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonochloridates with diethylamine gives the corresponding phosphonamides, whose oxidation results in new O-alkyl N,N-diethyl[3,5-(di-tert-butyl-4-oxocyclohexa-2,5-diene-1-ylidene)methyl]phosphonamides.

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