The mechanism of acyl phosphonate reactions. Part I. The kinetics of the solvolyses of benzoyl and p-toluoyl phenylphosphonates in aqueous dioxan
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1434-1436
- https://doi.org/10.1039/p29730001434
Abstract
Rate constants have been determined for the neutral hydrolysis of benzoyl phenylphosphonate in 5, 20, and 40% aqueous dioxan and p-toluoyl phenylphosphonate in 20% dioxan. Acid catalysis, salt effects, and the addition of nucleophiles have been investigated in 20% dioxan at 295·5 K. It is concluded that the mechanism of hydrolysis is bimolecular addition to the acyl carbon atom to form a tetrahedral intermediate prior to phosphonate ion elimination.Keywords
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