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  2. Michael addition reaction - Wikipedia

    en.wikipedia.org/wiki/Michael_Addition_Reaction

    In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon.

  3. Thiol-ene reaction - Wikipedia

    en.wikipedia.org/wiki/Thiol-ene_reaction

    In organosulfur chemistry, the thiol-ene reaction (also alkene hydrothiolation) is an organic reaction between a thiol (R−SH) and an alkene (R 2 C=CR 2) to form a thioether (R−S−R'). This reaction was first reported in 1905, [ 1 ] but it gained prominence in the late 1990s and early 2000s for its feasibility and wide range of applications.

  4. N-Ethylmaleimide - Wikipedia

    en.wikipedia.org/wiki/N-Ethylmaleimide

    NEM is a Michael acceptor in the Michael reaction, which means that it adds nucleophiles such as thiols. The resulting thioether features a strong C–S bond and the reaction is virtually irreversible. Reaction with thiols occur in the pH range 6.5–7.5, NEM may

  5. Thiol - Wikipedia

    en.wikipedia.org/wiki/Thiol

    In organic chemistry, a thiol (/ ˈ θ aɪ ɒ l /; [1] from Ancient Greek θεῖον (theion) 'sulfur' [2]), or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a ...

  6. Nucleophilic conjugate addition - Wikipedia

    en.wikipedia.org/wiki/Nucleophilic_conjugate...

    In the Nagata reaction the cyanide source is diethylaluminum cyanide. The Gilman reagent is an effective nucleophile for 1,4-additions to conjugated carbonyls. The Michael reaction involves conjugate additions of enolates to conjugated carbonyls. The Stork enamine reaction involves the conjugate addition of enamines to conjugated carbonyls.

  7. Click chemistry - Wikipedia

    en.wikipedia.org/wiki/Click_chemistry

    The classic [13] [14] click reaction is the copper-catalyzed reaction of an azide with an alkyne to form a 5-membered heteroatom ring: a Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The first triazole synthesis, from diethyl acetylenedicarboxylate and phenyl azide, was reported by Arthur Michael in 1893. [ 15 ]

  8. List of organic reactions - Wikipedia

    en.wikipedia.org/wiki/List_of_organic_reactions

    Michael addition, Michael system; ... Thiol-yne reaction; Thorpe reaction; Tiemann rearrangement; Tiffeneau ring enlargement reaction; Tiffeneau–Demjanov rearrangement;

  9. Maleimide - Wikipedia

    en.wikipedia.org/wiki/Maleimide

    The double bond readily undergoes a retro-Michael reaction with the thiol group found on cysteine to form a stable carbon-sulfur bond. Cysteines are often used for site-selective modifications for therapeutic purposes because of the rapid rate of complete bioconjugation with sulfhydryl groups, allowing for higher levels of cytotoxic drug ...