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Substituent effects in the acid-catalysed hydrolysis of alkylphenylphosphinanilides

✍ Scribed by Martin J.P. Harger; Andrew J. Macpherson; David Pickering

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
128 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

Haake and Tyssee' postulated a dissociative (Al or Al-like) mechanism for the acidcatalysed hydrolysis of diphenylphosphinanilides 1. They considered cleavage of theP-N bond in the protonated anilide to be well advanced in the transition state 2 and nucleophilic participation by water to be small. Although there is no reason to expect alkylphenylphosphinanilides to react by a fundamentally different mechanism, we observed a marked decline in the rate of hydrolysis of

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