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

Citation
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
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
53
Issue
37
Year of publication
1997
Pages
12691 - 12698
Database
ISI
SICI code
0040-4020(1997)53:37<12691:AH.SOT>2.0.ZU;2-8
Abstract
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.