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Original Articles

HYDROXYALKANESULFONYL CHLORIDES FROM CHLORINATION OF HYDROXYALKANESULFINATE SALTS IN A NONPOLAR MEDIUM: 3-HYDROXY-1-PROPANESULFONYL AND 4-HYDROXY-1-BUTANESULFONYL CHLORIDES

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Pages 165-171 | Received 18 Dec 1986, Published online: 19 Dec 2006

References

  • Part 33 in the series Organic Sulfur Mechanisms; for Part 32 see ref. 2.
  • King , J. F. , Webster , M. R. , Chiba , N. , Allen , J. K. , Parker , K. J. M. , Rathore , R. and Skonieczny , S. Phosphorus and Sulfur , in press
  • King , J. F. and Hillhouse , J. H. 1981 . J. Chem. Soc. Chem. Comm. , : 295
  • King , J. F. and Hillhouse , J. H. 1983 . Can. J. Chem. , 61 : 1583
  • King , J. F. , Skonieczny , S. , Khemani , K. C. and Stothers , J. B. 1983 . J. Am. Chem. Soc. , 105 : 6514
  • King , J. F. and Khemani , K. C. 1985 . Can. J. Chem. , 63 : 619 See, for example
  • Bellamy , L. J. 1961 . “Organic Sulfur Compounds,” , Edited by: Kharasch , N. Vol. 1 , 47 – 56 . Oxford : Pergamon Press . Typical frequencies for RSO− 2 are 1020 and 980 cm−1:
  • For reasons detailed elsewhere4 it seems likely that hydroxymethanesulfonyl chloride, HOCH2SO2Cl, the first member of this series, will prove unstable at room temperature, and hence that the compounds listed in Table I represent the first five accessible members of the set.
  • Also known as “effective molarities” (EM), and defined as Ceff = k 1/k 2 where k 1 is the first order rate constant for the cyclization and k 2 the second order rate constant for an appropriate model reaction.
  • Kirby , A. J. 1980 . Adv. Phys. Org. Chem. , 17 : 183 For a recent review see
  • Kaiser , E. T. 1970 . Acc. Chem. Res. , 3 : 145
  • Dellaria , J. F. Jr. , Nordeen , C. and Sweat , L. R. 1986 . Syn. Comm. , 16 : 1043 Cf.

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