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 Wroclawska, Department of Chemistry, Wybrzeze Wyspianskiego
27, 50370 Wroclaw, Poland, Email: miroslaw.soroka
pwr.wroc.pl
W. Goldeman, M. Soroka, Synthesis, 2006, 3019-3024.
DOI: 10.1055/s-2006-950200
Abstract
A very convenient reaction of trialkyl phosphites with aldehydes or ketones in the presence of hydrogen chloride gives dialkyl 1-hydroxyalkylphosphonates in good yields via an Arbusov-like reaction of oxonium salts derived from aldehydes or ketones. This reaction is an alternative to the well-known Abramov reaction.
see article for more examples
proposed mechanism
Key Words
Abramov reaction, nucleophilic addition, addition reactions, 1-hydroxyphosphonates
ID: J66-Y2006-2940
