J. Dhau, Rupy Dhir, Amritpal S. Singh
Aug 1, 2013
Citations
0
Influential Citations
6
Citations
Journal
Inorganica Chimica Acta
Abstract
Abstract The utility of BF 3 -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-BF 3 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 π⋯π stacking interactions between the pyridine rings in 9 .