Aarnav - 16-11-2016 at 09:19
Can we do MITSUNOBU reaction of a primary aliphatic amide and an alcohol
Ex:n-butylamide
clearly_not_atara - 16-11-2016 at 17:28
The Mitsunobu reaction depends on the triphenylphosphine/diazo complex deprotonating the target nucleophile; I doubt that n-butylamide will be
deprotonated. If you use an amide instead it probably will not attack the alkoxyphosphonium intermediate.
CuReUS - 17-11-2016 at 02:45
according to wiki,for the mitsunobu reaction to work,the nucleophile must have a pKa less than 15.For comparison,the pKa of acetamide is 16.5.
this paper might help you get what you want-https://www.thieme-connect.de/DOI/DOI?10.1055/s-0033-1340142
Aarnav - 17-11-2016 at 09:04
Thanks