Aryl H-phosphonates. 7. Studies on the formation of phosphorus-carbon bond in the reaction of trityl and benzyl halides with dialkyl and diphenyl H-phosphonates

Article abstract of DOI:10.1016/S0040-4020(97)00790-4

The reactions of H-phosphonate diesters with trityl and benzyl halides were investigated using ³¹P NMR spectroscopy. It was found that extensive oxidation, which usually accompanies the formation of trityl- or p-nitrobenzylphosphonates from the corresponding alkyl bromides in the Michaelis-Becker reaction, can be considerably suppressed or completely eliminated by reacting p-nitrobenzyl or trityl bromides with diphenyl H-phosphonate in acetonitrile in the presence of DBU.