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Reaction of furan with chloroform

  1. Dec 1, 2015 #1

    Titan97

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    1. The problem statement, all variables and given/known data
    What is the major product of the following reaction?
    EVxC8.png
    (Its CHCl3)

    2. Relevant equations
    Reimer Tieman reaction

    3. The attempt at a solution
    This reaction looks like the Riemer-Tiemann reaction. The only difference is the reactant. First step is the formation of carbene.
    Then either of the reactions are possible:
    IXMtR.png

    But since carbene does not react like an electrophile, It seeks the carbon with higher electron density. That is, it attacks position 3 or 4 to form product (B).
    But in case of Pyrole, the major products are:
    ua4oh.jpg

    Why is there a difference in the type of products?
     
  2. jcsd
  3. Dec 1, 2015 #2

    DrDu

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    Why not?
     
  4. Dec 1, 2015 #3

    Titan97

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    I meant reimer tiemann reaction is not like electrophilic aromatic substitution but involves carbanion formation.
     
  5. Dec 1, 2015 #4

    DrDu

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    One doesn't exclude the other.
     
  6. Dec 1, 2015 #5

    Titan97

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    Why doesn't Furan react like pyrrole towards carbene?
     
  7. Dec 2, 2015 #6

    Titan97

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    Is there any problem with my question?
     
  8. Dec 2, 2015 #7

    DrDu

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    No, just that I don't know the answer.
     
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