Studies on the reaction of trityl derivatives with H-phosphonate diesters: Their relevance to the synthesis of 4-pyridylphosphonates

✍ Scribed by Annika Kers; Leszek Dembkowski; Adam Kraszewski; Jacek Stawinski

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 190 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:6<492::aid-hc10>3.0.co;2-d

✦ Synopsis

Transesterification of diphenyl H-phos-

phonate with tritanol in pyridine afforded equimolar amounts of phenyl H-phosphonate monoester and diphenyl 4-pyridylphosphonate as the only phosphoruscontaining species. Using 31 P NMR spectroscopy a plausible reaction pathway for the observed transformation was proposed and some of the postulated intermediates were identified. These studies also enabled us to develop an efficient protocol for the formation of diphenyl and diethyl 4-pyridylphosphonates from the corresponding H-phosphonate diesters under mild reaction conditions.