hello everyone,
I want to deprotonate N-H proton from DMAc and use my conjugation base for substituting Fluoride from di-cyanotetrafluoro benzene, I tried base-solvent system like NaH-THF (rt-90*C) , NaH-DMF, t-BuOK/CH3CN, but I'm not able to deprotonate it, because TLC shows DMAc + new spots. but after workup, I have NMR of DMAc.
Dear Dr Vishvam Patel,
I think this document (in attached) may actually help you in your research.
Best wishes,
Sabri
Dear Dr. Mohamed Sabri,
I appreciate your concern towards the question, but I'm aware about the pdf, yet the deprotonation of DMAc should be done by NaH (as seen over years and chemistry) but the issue is attacking DMAc to Fluorine position (SNAr).
Check https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Structure_and_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_(Schaller)/I%3A__Chemical_Structure_and_Properties/14%3A_Concepts_of_Acidity/14.11%3A_Factors_Affecting_Bronsted-Lowry_Acidity-_Local_Factors
http://home.miracosta.edu/dlr/acids_bases.htm
Also check on this
https://pubs.rsc.org/en/content/articlehtml/2022/ma/d1ma00506e
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