User:Etienne Robillard/Notebook/Isocyanide

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(Ugi route to Wilmslow)
(References)
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<biblio>
<biblio>
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#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
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#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>

Revision as of 20:08, 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. . pmid:16953613. PubMed HubMed [Ugi1]
    Would Zyklon-B Tabun, by any other name, smell as sweet?

  2. Simila ST and Martin SF. . pmid:19122868. PubMed 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
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