Suggestions Required On How Can I Make Below Compound Reactive ?
Basically,I Want To Couple This Compound With The Other (Which Is Highly Reactive).
I Have Tried Converting In Sodium Salt And Dispersing It By Some Dispersants And Solvents But That Doesn't Providing Me The Desirable Results.
Comments And Suggestions Will Be Highly Appreciated.
Dear Daniyal, which position do you want to acivate in this molecule? The chlorine? And what do you want to react it with? Your question is not specific enough, so that we may help you without educated guessing.
You could consider using an oxime/hydrazone ligation through the ketone group. This involves condensation with a hydrazine or hydroxylamine of your other partner. Alternatively, you could try reductive amination with the ketone if you have a primary amine in your partner.
Dear Luc Alders , Thankyou Sir !
Not Chlorine Actually, I Want To Activate The CH2 Group Between Two Carbonyll Groups.
The Compound I Want It To React With Is A Tetrazonium Salt. (Double Azo Groups On Both Sides Of The Compound).
I Hope It Clarifies My Question.
Best Regards,
Daniyal
Dear Spencer J Williams ,
Thankyou For Your Suggestion.
I Have Tetrazonium Salt As My Other Coupling Compound Which Is Quit Unstable And Only Sustains In Low Temperature.
I Want My Tetrazonium Compound To Couple At CH2 Group Between Carbonyll Groups.
Hope You Will Give Suggestion On This.
Regards,
Daniyal
Although the compound is not totally clear, but if you are talking about coupling through C-C formation, the make use of a strong base. You can also look at Claisen condensation if it can help
Hello, If I am getting it right you want to C-C bond with the methylene next the two C=O. If that is the case, you could use a strong base (such as nBuLi)to deprotonate it at low temperature (-78ºC) and inert atmosphere. The resulting enolate will be highly reactive. I hope this helps.
I don't think you really need such a strong base as n-BuLi to deprotonate the methylene group in this substrate; bases like NaH of t-BuOK would be sufficient (even K2CO3 in aprotic solvents is used successfully for alkylation of malonates). In this particular case perhaps the electrophile is not reactive enough.
Also, let's not forget that we have an amide NH in a molecule, which is also pretty acidic, perhaps more acidic than methylene. Chances are that you may need to use more than one equivalent of the base. And of course for good results the reaction media should be anhydrous.
Thankyou Dear Vanderson Barbosa Bernardo & Vladimir Khlebnikov .
I Will Surely Try As Prescribed.
Subject your reactants to two model reactions.
Use sodium diethyl malonate and react with youtr tetrazonium salt. See if any product is formed. Since you have mentioned that tetrazonium salt is unstable.
In second model reaction, generate anion of methylene group and quench with highly reactive electrophile to see the reactivity.
Based on the outcome, the reaction condition can be suitably achieved.
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