ORGLIST: chlorosulfation

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From: Jay (hi_buddy03$##$yahoo.com)
Date: Mon Jan 08 2007 - 17:29:34 EST


Hello all,
  I am trying to perform a chlorosulfation reaction as an intermediate step.
  The reaction is as follows:
  Ar-CH2OH + SO2Cl2 --------> Ar-CH2OSO2Cl
  (3 mol) (3.6mol)
   
  Toluene as solvent and pyridine as a base.
  I am monitoring this reaction on HPLC but I cannot see anything other than the starting material peak.
  I thought SO2Cl2 being very reactive would give the product easily.
  I need some feedback on as to whether the method that I am using for synthesis has flaws or the reaction monitoring method is incorrect?
  If anybody has a new approach to this synthesis should also be fine.
   
  Thanks,
  Jay
   
   

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