How Can Isoxazole Be Synthesized from Furoxan and Phenylacetylene?

  • Topic: Chemistry 
  • Thread starter Thread starter Natalie456
  • Start date Start date
  • Tags Tags
    Formation Mechanism
Join the discussion
Registration is free. Start your own thread to ask a follow-up.
Sign up Log in
1 reply · 2K views
Natalie456
Messages
16
Reaction score
2
Homework Statement
Provide a mechanism for the conversion of the furoxan with phenylacetylene and DMF to create the isoxazole.
Relevant Equations
1,3 - dipolar cycloaddition?
Screen Shot 2020-02-23 at 2.38.28 AM.png

I'm having difficulties uploading my work to this system at the moment, but I have currently attempted 1,3-cycloaddition between the furoxan and phenylacetylene. However, unless a sigmatropic rearrangement occurs (which, as far as I can conclude, leads to instability with charges), this places the methyl and phenyl groups in the incorrect places. Is there a better way to, perhaps, go about this mechanism? Thank you.
 
Physics news on Phys.org

Discussion

Natalie456 said:
Homework Statement:: Provide a mechanism for the conversion of the furoxan with phenylacetylene and DMF to create the isoxazole.
Relevant Equations:: 1,3 - dipolar cycloaddition?

I'm having difficulties uploading my work to this system at the moment
Yeah unfortunately there aren't really any good options.

The only thing I can think to help you out with your question is that unsymmetrically substituted furoxans can sometimes isomerize between the two forms:
furoxan isomerization.png

This form gets you closer with 1,3-dipolar cycloaddition.

Edit: here's a reference to furoxan isomerization:
https://link.springer.com/article/10.1007/BF00519947

Further edit: obviously the tetravalent nitrogens have a +1 formal charge. Dunno why the drawing program didn't take care of that automatically.
 
Last edited: