oa South African Journal of Chemistry - Phosphoric amides: part 6:1 intramolecular nucleophilic displacement in ?-haloethyl-substituted phosphoramidates
|Article Title||Phosphoric amides: part 6:1 intramolecular nucleophilic displacement in ?-haloethyl-substituted phosphoramidates|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Affiliations||1 *Department of Organic Chemistry, University of Cape Town, Rondebosch & **Department of Organic Chemistry, University of Cape Town, Rondebosch.|
|Publication Date||Jan 1982|
|Pages||63 - 66|
|Keyword(s)||?-haloethyl-substituted amidoesters, Amide nitrogen atom, Aziridine derivatives, Electrophilic and basic catalysis, Halide ion, Intramolecular nucleophilic displacement, Phosphoric acid and Phosphoryl oxygen atoms|
Intramolecular nucleophilic displacement of halide ion from the ?-haloethyl-substituted amidoesters of phosphoric acid was studied under conditons of electrophilic and basic catalysis. 1,3-Substitution by the amide nitrogen atom, leading to the aziridine derivatives, was found to be the preferred reaction pathway; the alternative 1,5-reaction, involving the amide nitrogen or phosphoryl oxygen atoms, was not observed.
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