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Chlorination of Aliphatic Primary Alcohols via Triphosgene–Triethylamine Activation

Author:
Ayala, Caitlan E., Villalpando, Andres, Nguyen, Alex L., McCandless, Gregory T., Kartika, Rendy
Source:
Organic letters 2012 v.14 no.14 pp. 3676-3679
ISSN:
1523-7052
Subject:
alcohols, chemical structure, chlorination, triethylamine
Abstract:
Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.
Agid:
5784085