2,6-Bis(pent-4-enyloxy)aniline

[sumi]

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

[UC]

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.

[Horza2002]

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