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Preparation of new imidazol-2-yl-(amino)methylphosphonates,phosphinates and phosphine oxides and their unexpected cleavage under acidic conditions
Authors:Bogdan Boduszek  Tomasz K. Olszewski  Waldemar Goldeman  Kamila Grzegolec  Patrycja Blazejewska
Affiliation:Faculty of Chemistry, Department of Organic Chemistry, Wroclaw University of Technology, Wybrzeze St. Wyspianskiego 27, 50-370 Wroclaw, Poland
Abstract:The efficient synthesis of new imidazol-2-yl-(amino)methylphosphonic acids, phosphonates phosphinate esters and phosphine oxides is described. The synthetic methodology is based on nucleophilic addition of phosphorus species to imidazole-2 derived imines. Additionally, it was discovered that heating the imidazol-2-yl-(amino)methylphosphonates with aqueous HCl or H2SO4 leads to their decomposition resulting in a rupture of the C–P bond, elimination of the phosphorous-containing fragment and formation of the corresponding secondary imidazole-2 alkylamines. A mechanistic pathway for the cleavage is postulated.
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