Acyloxy derivatives of trivalent phosphorus in amidoalkylation of hydrophosphoryl compounds
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In order to model the previously suggested mechanism of the P-C bond formation via the Arbuzov reaction, we have studied the interaction of diethylacylphosphite (prepared beforehand as well as generated in situ from tetraethylpyrophosphite) with the in situ generated acyliminium cation. Various conditions of in situ generation of acylphosphite derivatives of P(III) from hydrophosphoryl compounds and acyliminium ions from N,N′-alkylidenebiscarbamates have been investigated: solvent nature, acid catalyst, and the reagents mixing order). The results obtained have confirmed the suggested mechanism of three-component reaction of amidoalkylation of hydrophosphoryl compounds with the formation of P-C bond via the Arbuzov reaction of in situ formed intermediates.
KeywordsAcetic Anhydride Methylphosphonous Acid Diethylphosphite Trivalent Phosphorus Arbuzov Reaction
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- 6.Yuan, S., Wang, G., and Chen, S., Synthesis, 1990, no. 6, p. 522.Google Scholar
- 7.Pudovik, A.N., Kashevarova, E.I., and Gorchakova, V.M. Zh. Obshch. Khim., 1964, vol. 34, no. 7, p. 2213; Fursenko, I.V., Bakhvalov, G.T., and Nifantev, E.E., Zh. Obshch. Khim., 1968, vol. 38, no. 4, p. 1299.Google Scholar
- 8.Kurdyukova, N.R., Rozhko, L.F., Ragulin, V.V., and Tsvetkov, E.N., Zh. Obshch. Khim., 1997, vol. 67, no. 12, p. 1965; Kurdyukova, N.R., Rozhko, L.F., Ragulin, V.V., and Tsvetkov, E.N., Zh. Obshch. Khim., 1997, vol. 67, no. 12, p. 1970; Rozhko, L.F. and Ragulin, V.V., Amino Acids, 2005, vol. 29, no. 2, p. 139.Google Scholar