The present invention provides a method for efficiently manufacturing a phosphonate ester by phosphonylating an alcohol under mild conditions, and a method for manufacturing a phosphate ester. In the method for manufacturing a phosphonate ester of the present invention, a compound represented by the formula (1) is reacted with a compound represented by the formula (2) in the presence of a zinc catalyst to obtain a compound represented by the formula (3).

##STR00001##

X represents an organic group. R.sup.1 represents an alkyl group. R.sup.2 represents an organic group.

Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

The present invention relates to a phosphorous acid compound represented by formula (I): ##STR00001##
wherein R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.5-8 cycloalkyl group, a C.sub.6-12 alkyl cycloalkyl group, a C.sub.7-12 aralkyl group or a C.sub.6-12 aryl group; R.sub.2 represents a hydrogen atom or a C.sub.1-3 alkyl group; and R.sub.3 represents a C.sub.3-25 alkylene group, a stabilizer for organic materials containing the phosphorous acid compound, a method for stabilizing an organic material in which the phosphorous acid compound is added to the organic material, and a stabilized organic material composition containing an organic material and the phosphorous acid ester compound.

The present invention relates to a phosphorous acid compound represented by formula (I):

##STR00001##

wherein R.sub.1 represents a C.sub.1-8 alkyl group, a C.sub.5-8 cycloalkyl group, a C.sub.6-12 alkyl cycloalkyl group, a C.sub.7-12 aralkyl group or a C.sub.6-12 aryl group; R.sub.2 represents a hydrogen atom or a C.sub.1-3 alkyl group; and R.sub.3 represents a C.sub.3-25 alkylene group, a stabilizer for organic materials containing the phosphorous acid compound, a method for stabilizing an organic material in which the phosphorous acid compound is added to the organic material, and a stabilized organic material composition containing an organic material and the phosphorous acid ester compound.