N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-11, Vol.75 (21), p.7141-7145
Main Authors: Marchenko, Anatolii P, Koidan, Heorgii N, Huryeva, Anastasiya N, Zarudnitskii, Evgeniy V, Yurchenko, Aleksandr A, Kostyuk, Aleksandr N
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Imidazolidines - chemistry
Nitrogen - chemistry
Organic chemistry
Phosphorus - chemistry
Phosphorylation
Preparations and properties
Reactivity and mechanisms
Salts - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101177h