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Preparation of α-Haloacrylate Derivatives via Dimethyl Sulfoxide-Mediated Selective Dehydrohalogenation

Wei Li,* Jianchang Li, Zhao-Kui Wan, Junjun Wu and Walter Massefski

*Chemical and Screening Sciences, Wyeth Research, 200 Cambridge Park Drive, Cambridge, Massachusetts 02140, Email: weiliwyeth.com

W. Li, J. Li, Z.-K. Wan, J. Wu, W. Massefski, Org. Lett., 2007, 9, 4607-4610.

DOI: 10.1021/ol7021142 (free Supporting Information)



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Abstract

α,β-Dihalopropanoate derivatives undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues in the presence of DMSO. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro- and bromoacrylonitriles.

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Dimethyl Sulfoxide Mediated Elimination Reactions in 3-Aryl 2,3-Dihalopropanoates: Scope and Mechanistic Insights

W. Li, J. Li, M. Lin, S. Wacharasindhu, K. Tabei, T. S. Mansour, J. Org. Chem., 2007, 72, 6016-6021.


Key Words

unsaturated compounds, vinyl bromides


ID: J54-Y2007-3470