
%0 Journal Article
%A Maynard, JA 
%A Swan, JM 
%T Organophosphorus Compounds. I. 2-Chloroalkylphosphonic Acids as Phosphorylating Agents
%J Australian Journal of Chemistry
%D 1963/08/01
%V 16
%N 4
%P 596-608
%K 
%R https://doi.org/10.1071/CH9630596
%U https://www.publish.csiro.au/paper/CH9630596 
%X Alcohols and phenols are phosphorylated in high yield by reaction with various 2-chloroalkylphosphonic acids at 20-50°C in the presence of three or more molar equivalents of cyclohexylamine or triethylamine, the other products being the corresponding alk-1-ene and chloride ion. The reaction probably proceeds by attack of an ROH molecule on the phosphorus atom of a doubly-ionized phosphonate group.   2-Chlorodecyl-, 10-carboxy-2-chlorodecyl-, and 2-chloro-octylphosphonic acid decompose rapidly in neutral solution giving chloride ion, phosphate ion, and the corresponding alk-1-ene. In the absence of hydroxylic compounds, 2-chlorodecylphosphonic acid is decomposed by cyclohexylamine to dec-1-ene and a product which appears to be N-cyclohexylphosphoramidate; t-amines and also aniline cause dehydrohalogenation to dec-1-enylphosphonic acid.   The proton magnetic resonance spectra of most of the phosphorus-containing substances described herein are recorded. 
