N-phosphorylated imidazolium salts as precursors to 2- and 5-phosphorylated imidazoles and new imidazol-2-ylidenes featuring the PNCN unit |
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Authors: | Marchenko Anatolii P Koidan Heorgii N Huryeva Anastasiya N Zarudnitskii Evgeniy V Yurchenko Aleksandr A Kostyuk Aleksandr N |
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Institution: | Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Str. 5, Kyiv-94, 02094, Ukraine. |
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Abstract: | 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(SiMe(3))(2) afforded new stable N-phosphorus-substituted Arduengo-type carbenes. |
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