benzbenz - 14-3-2007 at 22:50
Malononitrile can easily react with aldehyde or ketone in the condition of base. i did an experiment between malononitrile and ester, surprisly there
a new spot on TLC. They react?
Sauron - 14-3-2007 at 22:58
You don't believe your own TLC?
Repeat this on a prep scale, isolate and characterize your product. See what you made.
benzbenz - 14-3-2007 at 23:25
i did this experiment some months ago. Then i didn't have time to get pure product. i
just want to know whether esters can reacts with malononitrile. If can, how to explain
it.
mick - 15-3-2007 at 13:14
You could be talking about a knoevenagel condensation. Google "organic chemistry portal' and it should give the details. Malononitrile can condense
without the base
mick
benzbenz - 15-3-2007 at 18:31
yeah, this is a knoevenagel condensation. But i have no idea of the reaction between
malononitrile and ester. This issue isn't mentioned in knoevenagel condensation.
Sauron - 15-3-2007 at 20:48
Find a good thorough review of that reaction and see if it mentions anything about variations with esters. Org.Reactions and Chem.Rev. should be first
stops.
My initial hypothesis (read: wild guess) is that you abstracted a proton from malononitrile and acylated that active methylene with the ester (which
may have been saponified to the acid.)
Hard to say without knowing more about the reactants and conditions and what base you used if any.
If this is correct your product should be RC(=O)CH(CN)2
Not exactly a Knoevenagel. But close.
[Edited on 16-3-2007 by Sauron]