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Chlorination of Aliphatic Primary Alcohols via Triphosgene-Triethylamine Activation

Caitlan E. Ayala, Andres Villalpando, Alex L. Nguyen, Gregory T. McCandless and Rendy Kartika*

*Department of Chemistry, 232 Choppin Hall, Louisiana State University, Baton Rouge, Louisiana 70803, United States, Email: rkartikalsu.edu

C. E. Ayala, A. Villalpando, A. L. Nguyen, G. T. McCandless, R. Kartika, Org. Lett., 2012, 14, 3676-3679.

DOI: 10.1021/ol301520d (free Supporting Information)


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Abstract

Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products driven by sterics. The reaction conditions were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.


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Triphosgene-Amine Base Promoted Chlorination of Unactivated Aliphatic Alcohols

A. Villalpando, C. E. Ayala, C. B. Watson, R. Kartika, J. Org. Chem., 2013, 78, 3989-3996.


Key Words

alkyl chlorides


ID: J54-Y2012-2320