Difference between revisions of "User:Etienne Robillard/Notebook/Isocyanide"

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=== Ugi route to Wilmslow ===
 
=== Ugi route to Wilmslow ===
# Step 1: Protonation of the isocyanide carbonyl ('''C=O''') to yield a nucleophilic '''[[User:Etienne_Robillard/Notebook/Schiff_base|Schiff base]]''' via Hoffman/Ugi reaction: O+2ROH = -RN
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# Step 1: Protonation of the isocyanide carbonyl ('''C=O''') ester to yield a nucleophilic '''[[User:Etienne_Robillard/Notebook/Schiff_base|Schiff base]]''' via Hoffman/Ugi reaction: O+2ROH = -RN
  
 
=== References ===
 
=== References ===
  
 
<biblio>
 
<biblio>
#Hoffman1 pmid=16953613
+
#Ugi1 pmid=16953613
 
// Would <s>Zyklon-B</s> Tabun, by any other name, smell as sweet?  
 
// Would <s>Zyklon-B</s> Tabun, by any other name, smell as sweet?  
#Hoffman2 http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch17/ch17-3-4-2.html
+
#Ugi2 pmid=19122868
#Hoffman3 http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/aldket1.htm
+
// ketones variant (Scheme 5, figures 26c, 26d.)
 +
#Acetal1 http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch17/ch17-3-4-2.html
 +
#Acetal2 http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/aldket1.htm
 
#Wikipedia http://en.wikipedia.org/wiki/Isonitrile
 
#Wikipedia http://en.wikipedia.org/wiki/Isonitrile
 
</biblio>
 
</biblio>
 +
 +
=== 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  [https://en.wikipedia.org/wiki/Ether_Dome Ether Dome], a building located at the Massachusetts General Hospital in Boston.

Revision as of 19:18, 10 May 2013

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.