
TY  - JOUR
A1  - Maynard, JA 
A1  - Swan, JM 
T1  - Organophosphorus Compounds. I. 2-Chloroalkylphosphonic Acids as Phosphorylating Agents
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1963
VL  - 16
IS  - 4
SP  - 596
EP  - 608
KW  - 
UR  - https://doi.org/10.1071/CH9630596 
N2  - 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. 
ER  -

