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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 8
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Original Articles

β-Chloroalkyl Sulfides from Me2S/SO2Cl2/Me2SO and Alkenes

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Pages 1101-1108 | Received 16 Oct 1991, Published online: 23 Sep 2006

References

  • Wilson , G. E. 1982 . Tetrahedron , 38 : 2597
  • Oae , S. , Numana , T. and Yoshimura , T. 1981 . “The chemistry of the sulphonium group” , Edited by: Stirling , C. G. M. and Patai , S. 571 N. Y. : J. Wiley .
  • Tidwell , T. T. 1990 . Synthesis , : 857
  • Riche , M. A. 1855 . Ann. Chim. Phys. , 43 : 243
  • Martin , L. P. , Perozzi , E. F. and Martin , J. C. 1979 . J. Am. Chem. Soc. , 101 : 3595
  • Bordwell , F. G. and Pitt , B. M. 1955 . J. Am. Chem. Soc. , 77 : 572
  • Bellesia , F. , Ghelfi , F. , Pagnoni , U. M. and Pinetti , A. 1987 . J. Chem. Res. (S) , : 238
  • Bellesia , F. , Ghelfi , F. , Pagnoni , U. M. and Pinetti , A. 1987 . J. Chem. Res. (S) , : 24
  • Liu , H. G. and Nyangulu , J. M. 1988 . Tetrahedron Lett. , : 5467
  • DMSO produces a chlorosulfonium intermediate from both POC13 and phenyl dichloro phosphate
  • Liu , H. G. and Nyangulu , J. M. 1988 . Tetrahedron Lett. , : 3167
  • Liu , H. G. and Nyangulu , J. M. 1989 . Tetrahedron Lett. , : 5097
  • With DMSO-S02C12 the β-chloroalkyl sulfide is also obtained, but in lower yields, for example 63% from 1-octene, and with a remarkable amount of vicinal dichloride (i. e. 17% from 1-octene) and other unidentified products
  • Cis isomers from cyclic alkenes are virtually absent
  • With DES, the β-chloroalkyl sulfide (80% yield) is accompanied by some 1,2-dichloro octane (8% yield)
  • Schmid , G. H. , Strukely , M. , Dalipi , S. and Ryan , M. D. 1987 . J. Org. Chem. , 52 : 2403
  • Rasteikiene , L. , Greiciute , D. , Lin'kova , M. G. and Knunyants , I. L. 1972 . Russ. Chem. Rev. , 46 : 548
  • Smit , W. A. , Zefirov , N. S. and Bodrikov , I. V. 1981 . Organic Sulfur Chemistry , Edited by: Freidlina , R. Kh. and Skorova , A. E. 159 Oxford : Pergamon .
  • Since 1-octene is not attacked by chloromethyl methyl sulfide-DMSO, the possibility that the methanesulfenyl chloride could derive from the reaction of these compounds is also ruled out
  • Leplyanin , G. V. , Vorob'eva , A. I. , Sysoeva , L. B. and Varsil'eva , E. V. 1988 . Vysokomol. Soedin. , 30 : 2567 ser A
  • De Simone , J. M. , McGrath , J. E. and Smith , S. D. 1988 . Polym. Prepr. , 29 : 345

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