Synthesis, Table of Contents SHORTPAPER© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Chlorothioformates from XanthatesMegan 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, USAFax: +1(757)2212715; e-Mail: cjabel@wm.edu; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References <A NAME="RM03806SS-1">1</A> Martinez MA. Vega JC. Synthesis 1986, 760 <A NAME="RM03806SS-2">2</A> Zaim O. Tetrahedron Lett. 1999, 40: 8059 <A NAME="RM03806SS-3">3</A> Rao SR. Xanthates and Related Compounds Marcel Dekker; New York: 1971. <A NAME="RM03806SS-4">4</A> Castro EA. Chem. Rev. 1999, 99: 3505 <A NAME="RM03806SS-5">5</A> Barany G. Schroll AL. Mott AW. Halsrud DA. J. Org. Chem. 1983, 48: 4750 <A NAME="RM03806SS-6">6</A> Bergman J. Stalhandske C. Tetrahedron 1996, 52: 753 <A NAME="RM03806SS-7">7</A> Katritzky AR. Shcherbakova IV. Can. J. Chem. 1992, 70: 2040 <A NAME="RM03806SS-8">8</A> Masson E. Leroux F. Helv. Chim. Acta 2005, 88: 1375 <A NAME="RM03806SS-9">9</A> Larsen J. Lenoir C. Org. Synth. 1995, 72: 265 <A NAME="RM03806SS-10">10</A> Price CC. Stacy GW. Org. Synth. 1948, 28: 82
