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Topic: Reimer Tiemann reaction of furan and pyrrole  (Read 17348 times)

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Offline OsmiumTetroxide

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Reimer Tiemann reaction of furan and pyrrole
« on: December 02, 2015, 11:02:03 PM »
The major product of reaction of furan with chloroform in presence of a strong base is an aldehyde.
Since Riemer-Tiemann reaction involves nucleophilic attack of carbanion on dichlorocarbene, CCl2 gets attached to position 3 or 4. (This is because, the electron density at carbon near oxygen is reduced due to inductive effect)

Now, If pyrrole were to react with chloroform, these are the major products:

Why is there a difference in the products formed? Shouldn't dichlorocarbene attack position 3 or 4 for pyrrole as well?

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