74745-85-0Relevant articles and documents
THE ARBUZOV REACTION OF TRIETHYL PHOSPHITE WITH ELEMENTAL IODINE
Skowronska, S.,Pakulkski, M.,Michalski, J.,Cooper, D.,Trippett, S.
, p. 321 - 322 (1980)
Triethyl phosphite and elemental iodine in solution give transient iodotriethylphosphonium iodine which eliminates ethyl iodine to form diethyl phosphoroiodidate.An examination of the 31P NMR and IR spectra over the temperature range -100 deg C -0 deg C fails to disclose any evidence for triethoxydi-iodophosphorane, contrary to a previous claim.
Reaction of Boranephosphonate Diesters with Amines in the Presence of Iodine: The Case for the Intermediacy of H-Phosphonate Derivatives
Go??biewska, Justyna,Rachwalak, Marta,Jakubowski, Tomasz,Romanowska, Joanna,Stawinski, Jacek
, p. 5496 - 5505 (2018/05/28)
Mechanistic and stereochemical aspects of the reaction of boranephosphonate diesters with amines promoted by iodine were investigated. This is a complex, multistep reaction that ultimately produces the corresponding phosphoramidate diesters via a formal replacement of the borane group by an amine moiety. We found by a stereochemical correlation analysis that, contrary to a literature report, the whole transformation proceeded with total inversion of the configuration at the phosphorus center. Our study also showed that instead of the postulated nucleophilic substitution by iodide at the phosphorus center of the initially formed intermediate, the corresponding iodoboranephosphonate, the crucial step of the reaction involved intermediacy of H-phosphonate derivatives that reacted with iodine to afford ultimately phosphoramidate diesters. The reaction of the iodoboranephosphonate with the amine to produce an aminoboranephosphonate diester that rapidly dissociated into the corresponding H-phosphonate and the borane parts was apparently instrumental to the formation of an H-phosphonate diester intermediate.
