Neighbouring group-induced phosphorus–oxygen fission in acidic hydrolysis of phosphonates
Abstract
Anchimeric assistance by the neighbouring oxime function in acid hydrolysis of alkyl α-hydroxyimino-p-nitrobenzyl alkylphosphonates (III), besides increasing the rate of de-esterification by ca. 107 compared with simple phosphonates (I), leads to P–O fission, normally associated with alkaline hydrolysis of the latter.
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