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Reaction of thiols with vinyl ethers

  1. May 11, 2015 #1
    1. The problem statement, all variables and given/known data
    Find the product:
    Untitled.png
    2. Relevant concepts

    Thiols react with vinyl ethers according to anti-markovnikov's rule
    3. The attempt at a solution

    After reading Jerry March's book, i came to know that it follows free radical mechanism and that is why it gives anti markovnikov's product. Just like the peroxide effect. But its given that the reaction takes place in catalyst free conditions. What is the free radical initiator here? Untitled.png
     
  2. jcsd
  3. May 11, 2015 #2
    The interaction between oxygen in vinyl ether and hydrogen in thiol activates the double bond. The beta carbon has a partial positive charge and attracts sulfur. Then the bond between sulfur and hydrogen is broken. The alpha carbon then abstracts the proton from oxygen, giving the anti-Markovnikov product.
     
  4. May 11, 2015 #3
    But it follows free radical mechanism.
     
  5. May 14, 2015 #4
    Are you sure?
    There must be given something else in your book?
    Initiation of free radical mechanism requires energy in form of UV rays or something else but here nothing more is given.
     
  6. May 14, 2015 #5
    Nothing else is given. Surprisingly, the reaction takes place in catalyst and solvent free conditions.
     
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