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Facile synthesis of benzimidazolin-2-chalcogenones: Nature of the carbon-chalcogen bond

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Title Facile synthesis of benzimidazolin-2-chalcogenones: Nature of the carbon-chalcogen bond
 
Creator MANJARE, ST
SHARMA, S
SINGH, HB
BUTCHER, RJ
 
Subject Chalcogenone
Thione
Selenone
Tellurone
Dihalochalcogenone
DFT
HETEROCYCLIC CARBENE COMPLEXES
RUTHENIUM CATALYSTS
COUPLING REACTIONS
OLEFIN METATHESIS
STABLE CARBENE
CHEMISTRY
LIGANDS
SE
2-SELENOIMIDAZOLINES
HYDROSILYLATION
 
Description A new method using chalcogennucleophiles E2-/E-2(2-) (E = S, Se, Te) for the convenient and highyield synthesis of benzimidazolin-2-chalcogenones has been developed. The reaction of strong nucleophiles E2-/E-2(2-) with various benzimidazolium salts under mild conditions afforded benzimidazolin-2-chalcogenones (10ae10g) in better yield compared to the other methods involving E-0 powder. Benzimidazolin-2-tellurones were found to be unstable when pyridyl/phenyl groups were bonded to one of the nitrogens of the benzimidazoliumsalts and the reaction led to the isolation of the corresponding diamines (12a and 12b). The selenones/tellurones could be easily oxidized to the corresponding dihaloderivatives (16ae16e) by the reaction of the chalcogenones with bromine/iodine. The nature of the carbonechalcogen double bond has been investigated with the help of single crystal X-ray, NMR spectroscopy and Density Functional Theory (DFT) calculations. (C) 2012 Elsevier B. V. All rights reserved.
 
Publisher ELSEVIER SCIENCE SA
 
Date 2014-10-15T16:42:42Z
2014-10-15T16:42:42Z
2012
 
Type Article
 
Identifier JOURNAL OF ORGANOMETALLIC CHEMISTRY, 71761-74
http://dx.doi.org/10.1016/j.jorganchem.2012.07.025
http://dspace.library.iitb.ac.in/jspui/handle/100/15238
 
Language en