1192013-58-3Relevant academic research and scientific papers
N-phosphorylated imidazolium salts as precursors to 2- and 5-phosphorylated imidazoles and new imidazol-2-ylidenes featuring the PNCN unit
Marchenko, Anatolii P.,Koidan, Heorgii N.,Huryeva, Anastasiya N.,Zarudnitskii, Evgeniy V.,Yurchenko, Aleksandr A.,Kostyuk, Aleksandr N.
, p. 7141 - 7145 (2010)
It has been experimentally proven that the reaction of 1- or 1,2-disubstituted imidazoles with diorganylphosphorus(III) halides proceeds via initial formation of N-phosporylated imidazolium salts. Treatment of these salts with strong bases results in phosphorylation of the parent imidazoles at the 2- or 5-positions, correspondingly. In a previous case, imidazol-2-ylidenes are formed as intermediates. With both N1 and N3 atoms bearing sterically demanding or/and π-donating groups, deprotonation of 1,3-disubstituted imidazolium salts with NaN(SiMe3)2 afforded new stable N-phosphorus-substituted Arduengo-type carbenes.
