Journal of the Chemical Society. Perkin transactions I p. 2127 - 2131 (1983)
Update date:2022-09-26
Topics:
Harger, Martin J. P.
The phosphonamidic chlorides RP(O)(Cl)NHBut (2; R=Me, Et, or Pri) can be prapared directly from the corresponding phosphonic dichlorides RP(O)Cl2 and t-butylamine. t-Butylphosphonic dichloride reacts with t-butylamine only at high temperatures and then gives the diamide ButP(O)(NHBut)2 as the only detectable product.The phosphonamidic chloride (2; R=But) can, however, be prepared indirectly by oxidation (SO2Cl2) of ButP(Cl)NHBut obtained from ButPCl2 and t-butylamine.The phosphonamidic chlorides react with t-butylamine and isopropylamine in dichloromethane at rates that are unusually insensitive to steric effects in both the substrate and the amine; the slowest reaction <(2; R=But) + ButNH2> is only 30 times slower than the fastest <(2; R=Me) + PriNH2>.This is attributed to the reactions proceeding by elimination-addition mechanisms rather than by nucleophilic attack at phosphorus.In competitive experiments with t-butylamine and isopropylamine a rather small preference (1.4-4.0) for formation of the product derived from the less hindered amine is consistent with the (partial) involvement of a reactive monomeric metaphosphonimidate intermediate.
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