Ashkenazi, Nissan published the artcileNucleophilic Displacements in Alkylphosphonates: P-O Versus P-C Bond Cleavage. A Combined DFT and Experimental Study, Quality Control of 866-23-9, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2013), 188(1-3), 106-110, database is CAplus.
Potential energy surfaces for the nucleophilic displacements at P in di-Me Me, chloromethyl, dichloromethyl, and trichloromethyl phosphonates were computed by DFT methods. Sequential introduction of Cl substituents at the Me group in Me phosphonates increases the stability of transition states and intermediates, which facilitates P-C bond cleavage. While nonsubstituted di-Me methylphosphonate may undergo exclusive P-O bond cleavage, the trichlorinated analog reacts exclusively via P-C bond dissociation to form dichlorocarbene, which was trapped by various olefins to form the corresponding gem-dichlorocyclopropanes.
Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 866-23-9. 866-23-9 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyltrichloromethylphosphonate, and the molecular formula is C5H10Cl3O3P, Quality Control of 866-23-9.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics