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The behaviour of carbanions of para-substituted benzylcyanides and ambident enolatestoward phosphorylation has been examined.In the former case the C-phosphorylation proceededsmoothly,while the ambident enolate ions derived either from β-diketones or from β-ketoesters gaveexclusively regiospecific O-phosphorylation products on reaction with diethyl phosphoryl chloride.The experimental results are well supported by reaction selectivity in terms of Eqo/Ec.oc/basedon EHMO calculation.
The behavior of carbanions of para-substituted benzylcyanides and ambident enolatestoward phosphorylation has been investigated. In the former case of C-phosphorylation proceededsmoothly, while the ambident enolate ions derived either from β-ketones or from β-ketoesters gaveexclusively regiospecific O-phosphorylation products on reaction with diethyl phosphoryl chloride. The experimental results are well supported by reaction selectivity in terms of Eqo / Ec. oc / basedon EHMO calculation.