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  2. Carbanion - Wikipedia

    en.wikipedia.org/wiki/Carbanion

    A carbanion is one of several reactive intermediates in organic chemistry. In organic synthesis, organolithium reagents and Grignard reagents are commonly treated and referred to as "carbanions." This is a convenient approximation, although these species are generally clusters or complexes containing highly polar, but still covalent bonds metal ...

  3. Peterson olefination - Wikipedia

    en.wikipedia.org/wiki/Peterson_olefination

    When the α-silyl carbanion contains only alkyl, hydrogen, or electron-donating substituents, the stereochemical outcome of the Peterson olefination can be controlled, [7] because at low temperature the elimination is slow and the intermediate β-hydroxysilane can be isolated. Once isolated, the diastereomeric β-hydroxysilanes are separated.

  4. Ylide - Wikipedia

    en.wikipedia.org/wiki/Ylide

    An ylide (/ ˈ ɪ l aɪ d /) [1] or ylid (/ ˈ ɪ l ɪ d /) is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons.

  5. Substitution reaction - Wikipedia

    en.wikipedia.org/wiki/Substitution_reaction

    Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to ...

  6. Diethyl malonate - Wikipedia

    en.wikipedia.org/wiki/Diethyl_malonate

    The carbanion (2) formed by reacting diethyl malonate (1) with a suitable base can be alkylated with a suitable electrophile. This alkylated 1,3-dicarbonyl compound ( 3 ) readily undergoes decarboxylation with loss of carbon dioxide, to give a substituted acetic acid ( 4 ):

  7. Reactive intermediate - Wikipedia

    en.wikipedia.org/wiki/Reactive_intermediate

    In chemistry, a reactive intermediate or an intermediate is a short-lived, high-energy, highly reactive molecule. When generated in a chemical reaction, it will quickly convert into a more stable molecule. Only in exceptional cases can these compounds be isolated and stored, e.g. low temperatures, matrix isolation. When their existence is ...

  8. Ring expansion and contraction - Wikipedia

    en.wikipedia.org/wiki/Ring_expansion_and_contraction

    Ring expansion and ring contraction reactions expand or contract rings, usually in organic chemistry. The term usually refers to reactions involve making and breaking C-C bonds, [1] Diverse mechanisms lead to these kinds of reactions. The bond migration step of the pinacol type rearrangement

  9. Organolithium reagent - Wikipedia

    en.wikipedia.org/wiki/Organolithium_reagent

    In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds.These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. [1]