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2,6-Bis(pent-4-enyloxy)aniline Rate Topic: -----

#1 8 November 2010 - 12:35 PM sumi 


Lepton
Hi, I have a problem figuring out the Mechanismus for this rxn:

2-nitroresorcinol + 4-penten-1-ol --> 2-Nitro-1,3-bis(pent-4-enyloxy)benzene --> 2,6-Bis(pent-4-enyloxy)aniline

Hope someone can help me with this,


sumi

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#2 8 November 2010 - 05:05 PM UC 


ydoaPs just lost the game
Look at the choice of reagents and then go looking for a named organic reaction that uses them. For example, DIAD is diisopropyl azodicarboxylate, the wikipedia page of which lists it as being used for the Mitsunobu reaction, which surprise, surprise, also uses PPh3.
Carnac: READ the vapors!
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#3 8 November 2010 - 07:16 PM Horza2002 


Baryon
As UC says, the first step is a Mitsunobu reaction that is used to form the arly-alky bonds. The second step is a Stephen reduction using tin(II) chloride. Its not really used anymore because there are more efficient ways to do it...commonly you'd use hydrogen gas with palladium/carbon. However, in this case, the alkenes would also be reduced with hydrogen with Pd/C
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