Two correlation methods of ionization constants of the organophosphorus acids are discussed. The first involves application of constants characteristic of the substituents bonded to phosphorus. In the second approach the and constants found for the substituents bonded to carbon are used. The best correlations are obtained for * constants. Correlation of constants with and values employing the Taft equation gives only a fairly good correlation coefficients. Electronic effects of the substituents at phosphorus are of the same nature as those at carbon atom, but some specific difference in the resonance effects is observed probably owing to the difference betweenorand p-d or n-d overlaps. Thus the use of constants for correlation of the organophosphorus reactions is preferable.
The reaction with chloral of 2-[1-(3-chlorophenyl)-2,2,2-trifluoroethoxy]-5,6-benzo-1,3,2-dioxaphosphorinan-4-one containing a chiral fluorinated exocyclic substituent on phosphorus leads to formation of 2-[1-(3-chlorophenyl)-2,2,2-trifluoroethoxy]-3-(trichloromethyl)-6,7-benzo-1,4,2l 5 -dioxaphosphepin-5-one 2-oxide with a high regio-and stereoselectivity. The molecular and supramolecular structure of the isolated diastereomer was established by means of X-ray diffraction.
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