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  2. Deprotonation - Wikipedia

    en.wikipedia.org/wiki/Deprotonation

    Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H +) from a Brønsted–Lowry acid in an acid–base reaction. [ 1 ] [ 2 ] The species formed is the conjugate base of that acid.

  3. Concerted metalation deprotonation - Wikipedia

    en.wikipedia.org/wiki/Concerted_metalation...

    Concerted metalation-deprotonation (CMD) is a mechanistic pathway through which transition-metal catalyzed C–H activation reactions can take place. In a CMD pathway, the C–H bond of the substrate is cleaved and the new C–Metal bond forms through a single transition state . [ 1 ]

  4. Protonation - Wikipedia

    en.wikipedia.org/wiki/Protonation

    Protonation and deprotonation (removal of a proton) occur in most acid–base reactions; they are the core of most acid–base reaction theories. A Brønsted–Lowry acid is defined as a chemical substance that protonates another substance.

  5. Organolithium reagent - Wikipedia

    en.wikipedia.org/wiki/Organolithium_reagent

    This generates a complex-induced proximity effect, which directs deprotonation at the α position to form an aryllithium species that can further react with electrophiles. Some of the most effective DMGs are amides, carbamates, sulfones and sulfonamides. They are strong electron-withdrawing groups that increase the acidity of alpha-protons on ...

  6. Enolate - Wikipedia

    en.wikipedia.org/wiki/Enolate

    The deprotonation of carbon acids can proceed with either kinetic or thermodynamic reaction control. For example, in the case of phenylacetone , deprotonation can produce two different enolates. LDA has been shown to deprotonate the methyl group, which is the kinetic course of the deprotonation.

  7. Sodium methoxide - Wikipedia

    en.wikipedia.org/wiki/Sodium_methoxide

    Sodium methoxide is prepared by treating methanol with sodium: 2 Na + 2 CH 3 OH → 2 CH 3 ONa + H 2. The reaction is so exothermic that ignition is possible. The resulting solution, which is colorless, is often used as a source of sodium methoxide, but the pure material can be isolated by evaporation followed by heating to remove residual methanol.

  8. Wittig reagents - Wikipedia

    en.wikipedia.org/wiki/Wittig_reagents

    The alkylphosphonium salt is deprotonated with a strong base such as n-butyllithium: [Ph 3 P + CH 2 R]X − + C 4 H 9 Li → Ph 3 P=CHR + LiX + C 4 H 10. Besides n-butyllithium (n BuLi), other strong bases like sodium and potassium t-butoxide (t BuONa, t BuOK), lithium, sodium and potassium hexamethyldisilazide (LiHMDS, NaHMDS, KHDMS, where HDMS = N(SiMe 3) 2), or sodium hydride (NaH) are also ...

  9. Cyclopentadiene - Wikipedia

    en.wikipedia.org/wiki/Cyclopentadiene

    Deprotonation can be achieved with a variety of bases, typically sodium hydride, sodium metal, and butyl lithium. Salts of this anion are commercially available, including sodium cyclopentadienide and lithium cyclopentadienide. They are used to prepare cyclopentadienyl complexes.