User:Etienne Robillard/Notebook/Isocyanide

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Ugi route to Wilmslow

  1. Step 1: Protonation of the isocyanide carbonyl (C=O) ester to yield a nucleophilic Schiff base via Hoffman/Ugi reaction: O+2ROH = -RN

References

  1. Pirrung MC and Ghorai S. Versatile, fragrant, convertible isonitriles. J Am Chem Soc. 2006 Sep 13;128(36):11772-3. DOI:10.1021/ja0644374 | PubMed ID:16953613 | HubMed [Ugi1]
    Would Zyklon-B Tabun, by any other name, smell as sweet?
  2. Simila ST and Martin SF. Applications of the Ugi reaction with ketones. Tetrahedron Lett. 2008;49(29-30):4501-4504. DOI:10.1016/j.tetlet.2008.05.073 | PubMed ID:19122868 | HubMed [Ugi2]
    ketones variant (Scheme 5, figures 26c, 26d.)
  3. http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch17/ch17-3-4-2.html [Acetal1]
  4. http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/aldket1.htm [Acetal2]
  5. http://en.wikipedia.org/wiki/Isonitrile [Wikipedia]
All Medline abstracts: PubMed | HubMed

Did you know?

In 1846, the first public demonstration of the use of ether vapors for chirurgical anesthesia was achieved by Dr. William T.G Morton at the Ether Dome, a building located at the Massachusetts General Hospital in Boston.