The Preparation of Dialkyl 1-Hydroxyalkylphosphonates in the Reaction of Trialkyl Phosphites with Oxonium Salts Derived from Aldehydes or Ketones

Waldemar Goldeman; Mirosław Soroka

doi:10.1055/s-2006-950200

PAPER

The Preparation of Dialkyl 1-Hydroxyalkylphosphonates in the Reaction of Trialkyl Phosphites with Oxonium Salts Derived from Aldehydes or Ketones

Waldemar Goldeman, Mirosław Soroka*
Politechnika Wrocawska, Department of Chemistry, Wybrze¿e Wyspiańskiego 27, 50370 Wrocaw, Poland
Fax: +48(71)3284064; e-Mail: miroslaw.soroka@pwr.wroc.pl;

Abstract

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Abstract

The reaction of trialkyl phosphites with aldehydes or ketones in the presence of hydrogen chloride gives dialkyl 1-hydroxyalkylphosphonates via Arbusov-like reaction of oxonium salts derived from aldehydes or ketones. This reaction is a very convenient instant method for the preparation of dialkyl 1-hydroxyalkylphosphonates with a good yield as an alternative to the well-known Abramov reaction.

Key words

Abramov reaction - nucleophilic addition - addition reactions - 1-hydroxyphosphonates

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Referenzen

References

Since citation of more than 500 papers in this short article is not appropriate we will send a copy of a text file with the citations to interested readers.

The chemistry of 1-hydroxyalkylphosphonic acids is of course much older. 1-Hydroxyalkylphosphonic acids were prepared in the 19^th and 20^th centuries by Marie and Fossek:

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Later, Conant described the preparation of some 1-hydroxyalkylphosphonic acids in the reaction of phosphorous (phosphonic) acid or phosphorus trichloride with aldehydes or ketones:

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