Organophosphorus Compounds. I. 2-Chloroalkylphosphonic Acids as Phosphorylating Agents

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Published
1963-08-01
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  • https://doi.org/10.1071/journalslicense
DOI
  • 10.1071/ch9630596
Publisher
CSIRO Publishing

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<jats:p>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.</jats:p>

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