What is the Major Product When Furan Reacts with Chloroform?

Join the discussion
Registration is free. Start your own thread to ask a follow-up.
6 replies · 5K views
Titan97
Gold Member
Messages
450
Reaction score
18

Homework Statement


What is the major product of the following reaction?
EVxC8.png

(Its CHCl3)

Homework Equations


Reimer Tieman reaction

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?
 
  • Like
Likes   Reactions: Sujith Sizon
Physics news on Phys.org
Titan97 said:
But since carbene does not react like an electrophile,
Why not?
 
  • Like
Likes   Reactions: Titan97
I meant reimer tiemann reaction is not like electrophilic aromatic substitution but involves carbanion formation.
 
  • Like
Likes   Reactions: Sujith Sizon
One doesn't exclude the other.
 
  • Like
Likes   Reactions: Titan97
Why doesn't Furan react like pyrrole towards carbene?
 
  • Like
Likes   Reactions: Sujith Sizon
Is there any problem with my question?
 
No, just that I don't know the answer.
 
  • Like
Likes   Reactions: Sujith Sizon and epenguin