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Synthesis 2007(14): 2097-2099
DOI: 10.1055/s-2007-983756
DOI: 10.1055/s-2007-983756
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
S-Alkyl Chlorothioformates from Xanthates
Weitere Informationen
Received
16 March 2007
Publikationsdatum:
03. Juli 2007 (online)
Publikationsverlauf
Publikationsdatum:
03. Juli 2007 (online)
![](https://www.thieme-connect.de/media/synthesis/200714/lookinside/thumbnails/10.1055-s-2007-983756-1.jpg)
Abstract
Reaction of S-alkyl O-ethyl xanthates (S-alkyl O-ethyl dithiocarbonates) with catalytic Vilsmeier reagent generated in situ from N-formylmorpholine (morpholine-4-carbaldehyde) gives S-alkyl chlorothioformates in good yields.
Key words
halogenation - desulfurization - Vilsmeier reagent - chlorothioformates - dithiocarbonates
- 1
Jiao L.Liang Y.Zhang Q.Zhang S.Xu J. Synthesis 2006, 659 - 2
Trudeau S.Deslongchamps P. J. Org. Chem. 2004, 69: 832 - 3
Snoonian JR.Platz MS. J. Phys. Chem. A 2000, 104: 9276 - 4
He M.Dowd P. J. Am. Chem. Soc. 1998, 120: 1133 - 5
Barany G.Schroll AL.Mott AW.Halsrud DA. J. Org. Chem. 1983, 48: 4750 - 6
Kollonitsch J.Gabor V.Hajos A. Chem. Ber. 1956, 89: 2293 - 7
Gilligan WH.Stafford SL. Synthesis 1979, 600 - 8
Kice JL.Bartsch RA.Dankleff MA.Schwartz SL. J. Am. Chem. Soc. 1965, 87: 1734 - 9
Carpino LA. J. Org. Chem. 1963, 28: 1909 - 10
Dyson GM. Chem. Rev. 1927, 4: 109 - 11
Sturm B.Gattow G. Z. Anorg. Allg. Chem. 1984, 508: 136 - 12
Lamoureux GV.Whitesides GM. J. Org. Chem. 1993, 58: 633 - 13
Mori K.Nakamura Y. J. Org. Chem. 1969, 34: 4170 - 14
Taguchi T.Kiyoshima Y.Komori O.Mori M. Tetrahedron Lett. 1969, 41: 3631 - 15
Olah GA.Schilling P.Bollinger JM.Nishimura J. J. Am. Chem. Soc. 1974, 96: 2221 - 16
Bajusz F,Bodi T,Foldi Z,Timko A,Zolnai L,Mihalyi A,Molnar I, andRacz L. inventors; HU 45973. ; Chem. Abstr. 1988, 100, 192263 - 17 inventors; Stauffer Chemical Co. GB 948831.
; Chem. Abstr. 1988, 60, 67857
- 18
Bergman J.Stalhandske C. Tetrahedron 1996, 52: 753 - 19
Katritzky AR.Shcherbakova IV. Can. J. Chem. 1992, 70: 2040 - 20
Tournier L.Zard SZ. Tetrahedron Lett. 2005, 46: 455 - 21
Kozikowski AP.Lee J. Tetrahedron Lett. 1988, 29: 3053 - 22
Mott AW.Barany G. J. Chem. Soc., Perkin Trans. 1 1984, 2615 - 23
Fikse MA.Bylund WE.Holubowitch NE.Abelt CJ. Synthesis 2006, 4118 - 24
Douglass IB.Norton RV.Cocanour PM.Koop DA.Kee M.-L. J. Org. Chem. 1970, 35: 2131 - 25
Degani I.Foshi R. Synthesis 1978, 365 - 26
DePuy CH.Bishop CA.Goeders CN. J. Am. Chem. Soc. 1961, 83: 2151 - 27
Zaitseva SP.Plaksin IN. Izv. Akad. Nauk SSSR, Otd. Tekh. Nauk 1956, 117 - 28
Trimnell D.Stout EI.Doane WM.Russell CR.Beringer V.Saul M.Van Gessel G. J. Org. Chem. 1975, 40: 1337 - 29
Barton DHR.George MV.Tomoeda M. J. Chem. Soc. 1962, 1967 - 30
Cusack J.Drew MGB.Spalding TR. Polyhedron 2004, 21: 2315 - 31
Gurudutt KN.Rao SR.Srinivas P.Srinivas S. Tetrahedron 1995, 51: 3045