PAPER	Synthesis 2006: 3019-3024   DOI: 10.1055/s-2006-950200
© Georg Thieme Verlag Stuttgart · New York
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;
Received 16 March 2006

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