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Straightforward synthesis of alkynyl imines via 1,2-elimination of α,α-dichloroketimines
Authors:Sven Mangelinckx
Institution:Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
Abstract:Alkylation of α,α-dichloroketimines at the α-position with benzyl bromides afforded β-arylated α,α-dichloroketimines in good yields. The latter imines could be easily transformed to the corresponding alkynyl imines, a synthetically important class of compounds, via 1,2-elimination of HCl upon treatment with 2 equiv of sodium hydride in DMSO or potassium tert-butoxide in THF.
Keywords:Alkynyl imines  3  3-Dichloro-1-azaallylic anions  1  2-Elimination  Alkynyl ketones
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