Synthesis and characterization of 4-(dimethylaminopyridyl)chalcogenides (Se, Te): X-ray structure of bis(4-dimethylamino-2-pyridyl) diselenide, bis(4-dimethylamino-2-pyridylselenenyl)methane and 4-dimethylamino-2,6-bis(methylselenenyl)pyridine
authors Dhau, JS; Dhir, R; Singh, A; Brandao, P; Felix, V
nationality International
journal INORGANICA CHIMICA ACTA
author keywords Organochalcogenide; Diselenide; Pyridylchalcogenide; 4-Dimethylaminopyridine
keywords PYRIDYLSELENO GROUP; SELENIUM-COMPOUNDS; CRYSTAL-STRUCTURE; COMPLEXES
abstract The utility of BF3-aided lithiation of 4-dimethylaminopyridine (1) with lithium diisopropylamide (LDA) or lithium tetramethylpiperidide (LTMP) in the synthesis of 4-(dimethylaminopyridyl)chalcogenides (Se, Te) has been studied. The lithiation of the in situ generated 4-dimethylaminopyridine-BF3 adduct (2) with LTMP (1.1 eq.) followed by chalcogen insertion and electrophilic quenching reaction afforded the corresponding pyridylchalcogenides in excellent yields. The use of LDA with a modified procedure gave pyridylchalcogenides in yields comparable to that obtained with LTMP. Single crystal X-ray studies of bis(4-dimethylamino-2-pyridyl) diselenide (6), bis(4-dimethylamino-2-pyridylselenenyl) methane (9) and 4-dimethylamino-2,6-bis(methylselenenyl)pyridine (11) have also been reported. The structural analysis reveals a rare cis, trans conformation among the bis(2-pyridyl) diselenides in 6 and pi center dot center dot center dot pi stacking interactions between the pyridine rings in 9. (C) 2013 Elsevier B. V. All rights reserved.
publisher ELSEVIER SCIENCE SA
issn 0020-1693
year published 2013
volume 404
beginning page 160
ending page 166
digital object identifier (doi) 10.1016/j.ica.2013.04.020
web of science category Chemistry, Inorganic & Nuclear
subject category Chemistry
unique article identifier WOS:000320651900021
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journal impact factor 2.304
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