ARYL H-PHOSPHONATES .7. STUDIES ON THE FORMATION OF PHOSPHORUS-CARBONBOND IN THE REACTION OF TRITYL AND BENZYL HALIDES WITH DIALKYL AND DIPHENYL H-PHOSPHONATES
A. Kers et al., ARYL H-PHOSPHONATES .7. STUDIES ON THE FORMATION OF PHOSPHORUS-CARBONBOND IN THE REACTION OF TRITYL AND BENZYL HALIDES WITH DIALKYL AND DIPHENYL H-PHOSPHONATES, Tetrahedron, 53(37), 1997, pp. 12691-12698
The reactions of H-phosphonate diesters with trityl and benzyl halides
were investigated using P-31 NMR spectroscopy. It was found that exte
nsive oxidation, which usually accompanies the formation of trityl- or
p-nitrobenzylphosphonates from the corresponding alkyl bromides in th
e Michaelis-Becker reaction, can be considerably suppressed or complet
ely eliminated by reacting p-nitrobenzyl or trityl bromides with diphe
nyl H-phosphonate in acetonitrile in the presence of DBU. (C) 1997 Els
evier Science Ltd.