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Synthesis 2006(24): 4118-4120  
DOI: 10.1055/s-2006-950356
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chlorothioformates from Xanthates

Megan A. Fikse, William E. Bylund, Nicolas E. Holubowitch, Christopher J. Abelt*
Department of Chemistry, College of William and Mary, PO Box 8795, Williamsburg, VA 23187, USA
Fax: +1(757)2212715; e-Mail: cjabel@wm.edu;
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Publication History

Received 26 May 2006
Publication Date:
02 November 2006 (online)

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Abstract

The Vilsmeier reagent derived from N-formylmorpholine produces chlorothioformates from primary and secondary alkyl xanthates. The major side products are the corresponding alkyl chlorides. Secondary alkyl chlorothioformates give lower yields due to their instability. Treating xanthates with other common chlorinating agents (oxalyl chloride, thionyl chloride) gives only dialkyl thiodicarbonates.

Key words

halogenation - xanthate desulfurization - Vilsmeier reagent­ - chlorothioformate synthesis - chlorothionocarbonates