A kinetic study of competing fragmentation and hydrolyses of phenyl hydrogen α-hydroxyiminobenzylphosphonate—a case of acid mediated inhibition of acid …

R Ta-Shma, H Schneider, M Mahajna…

Index: Ta-Shma, Rachel; Schneider, Hava; Mahajna, Mahmoud; Katzhendler, Jehoshua; Breuer, Eli Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 8 p. 1404 - 1407

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Abstract

The behavior of phenyl hydrogen α-hydroxyiminobenzylphosphonate (E)-2 in aqueous hydrochloric acid solution was examined by 31P NMR spectroscopy and by HPLC. Compound (E)-2 was found to undergo two competing acid-catalyzed reactions. 1) Fragmentation to phenyl phosphate (6) and benzonitrile, similar to the fragmentation of other hydroxyiminophosphonates to metaphosphate examined previously. The fragmentation of ...