A Useful Method for the Dealkylation of Dialkyl Phosphonates
- 1 January 1979
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 9 (2) , 97-102
- https://doi.org/10.1080/00397917908064135
Abstract
The conversion of dialkyl phosphonates (1) to phosphonic acids (2) is usually accomplished by heating 1 in concentrated HC1 or HBr.1 This method, however, is subject to interference by other functional groups. In connection with our synthetic studies on biologically active organophosphorus compounds, we were faced with the problem of effecting the dealkylation of 1 containing labile functional groups under mild conditions. At the time when we were engaged in this study, the only available method for this purpose was to heat 1 in chlorotrimethylsilane2. This reaction, albeit mild, takes several days and the yields are not always satisfactory. We wish to report a very mild and extremely efficient method for the dealkylation of 1. Our strategy for effect-Keywords
This publication has 3 references indexed in Scilit:
- The facile dealkylation of phosphonic acid dialkyl esters by bromotrimethylsilaneTetrahedron Letters, 1977
- Solvolytic fragmentation of 2-halogenoalkylphosphonic acidsJournal of the Chemical Society, Perkin Transactions 2, 1974
- The Reactions of Phosphonic Acid Esters with Acid Chlorides. A Very Mild Hydrolytic RouteThe Journal of Organic Chemistry, 1963