• Thumbnail for Iminium
    chemistry, an iminium cation is a polyatomic ion with the general structure [R1R2C=NR3R4]+. They are common in synthetic chemistry and biology. Iminium cations...
    6 KB (621 words) - 05:09, 22 August 2024
  • Thumbnail for Bis(triphenylphosphine)iminium chloride
    Bis(triphenylphosphine)iminium chloride is the chemical compound with the formula [((C6H5)3P)2N]Cl, often abbreviated [(Ph3P)2N]Cl, where Ph is phenyl...
    7 KB (591 words) - 06:48, 22 June 2024
  • Thumbnail for Vilsmeier reagent
    reactions, the anion is PO2Cl2−. The iminium cation [(CH3)2N=CHCl]+ is the reactive component of interest. This iminium species is a derivative of the imidoyl...
    3 KB (207 words) - 19:58, 30 September 2023
  • pathway. The driving force for this reaction is the electrophilicity of the iminium ion generated from the condensation of the aldehyde and amine under acid...
    11 KB (1,182 words) - 03:14, 23 January 2024
  • good leaving group for formation of the iminium ion, in accordance with its usage in iminium ion generation. Iminium ion generation from cyanomethyl groups...
    50 KB (5,704 words) - 20:45, 22 July 2024
  • Thumbnail for Photoredox catalysis
    compounds to form iminium ions is often unfavorable, sometimes requiring harsh dehydrating conditions. Thus, alternative methods for iminium ion generation...
    50 KB (6,218 words) - 23:10, 8 February 2024
  • Thumbnail for HATU
    and can exist as either the uronium salt (O-form) or the less reactive iminium salt (N-form). HATU was initially reported as the O-form using the original...
    10 KB (895 words) - 12:00, 1 August 2024
  • Thumbnail for Imidazolidinone
    forming an iminium ion with carbonyl groups of α,β-unsaturated aldehydes (enals) and enones in a rapid chemical equilibrium. This iminium activation lower...
    2 KB (226 words) - 01:45, 9 October 2023
  • Thumbnail for Eschweiler–Clarke reaction
    formation of the tertiary amine is more favorable, as the intermediate in iminium ion is formed without needing to protonate. Hence the treatment of a primary...
    4 KB (371 words) - 23:50, 14 February 2024
  • Thumbnail for Azomethine ylide
    Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions...
    18 KB (1,988 words) - 01:46, 19 April 2024
  • Thumbnail for Methamphetamine
    carbon dioxide and methylamine as side products. In this reaction, an iminium cation is formed as an intermediate which is reduced by the second equivalent...
    151 KB (14,850 words) - 16:49, 21 August 2024
  • An intermolecular formal [3+3] cycloaddition between an cyclic iminium chloride and cyclopentenone....
    11 KB (1,261 words) - 17:18, 22 January 2024
  • Thumbnail for Organocatalysis
    of an active enamine nucleophile) or iminium catalysis (by forming catalytic quantities of an activated iminium electrophile). This mechanism is typical...
    17 KB (1,720 words) - 11:46, 11 May 2024
  • Thumbnail for Imine
    parent amines, imines are mildly basic and reversibly protonate to give iminium salts: R2C=NR' + H+ ↽ − ⇀ {\displaystyle {\ce {<=>>}}} [R2C=NHR']+ Alternatively...
    23 KB (2,633 words) - 07:34, 30 May 2024
  • Thumbnail for Ibogaine
    The lactol opens and produces an aldehyde, then condenses to form an iminium. Through isomerization and reduction by geissoschizine synthase 1 (GS1)...
    58 KB (5,961 words) - 06:34, 25 August 2024
  • each resonance structure, exactly one nitrogen atom is oxidized to an iminium. Typically, they form part of a nitrogenous heterocyclic system. The main...
    17 KB (1,827 words) - 07:44, 7 June 2024
  • chloride (SnCl2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH2]+Cl−) with water (H2O). During the synthesis, ammonium...
    5 KB (471 words) - 10:23, 11 August 2024
  • substituent groups may be divalent or trivalent, yielding ions such as iminium and nitrilium. A simple onium ion has a charge of +1. A larger ion that...
    16 KB (1,499 words) - 15:22, 4 December 2023
  • Thumbnail for Folate
    dehydrogenase (MTHFD2) oxidizes 5,10-methylenetetrahydrofolate to an iminium cation which in turn is hydrolyzed to produce 5-formyl-THF and 10-formyl-THF...
    101 KB (11,049 words) - 02:09, 19 August 2024
  • The mechanism of the Mannich reaction starts with the formation of an iminium ion from the amine and formaldehyde.: 140  The compound with the carbonyl...
    10 KB (1,013 words) - 23:01, 13 January 2024
  • Thumbnail for Sodium cyanoborohydride
    used for the reduction of imines. These reactions occur <pH 7 because the iminium ions are the actual substrates. Reductive amination, sometimes called the...
    9 KB (792 words) - 14:48, 1 April 2024
  • Thumbnail for Nile red
    boiling a solution of Nile blue with sulfuric acid. This process replaces an iminium group with a carbonyl group. Alternatively, Nile red and its analogs (naphthooxazine...
    8 KB (739 words) - 23:51, 22 October 2023
  • Thumbnail for Berberine
    N-methyl group, supplied by S-adenosyl methionine (SAM), is oxidized to an iminium ion, and a cyclization to the aromatic ring occurs by virtue of the phenolic...
    11 KB (875 words) - 14:36, 13 May 2024
  • Thumbnail for Dichloromethane
    reaction. Secondary amines can react with DCM to yield an equilibrium of iminium chlorides and chloromethyl chlorides, which can react with a second equivalent...
    29 KB (2,592 words) - 14:25, 17 July 2024
  • any primary or secondary amine to produce resonance stabilized imine (iminium ion or imine salt). The addition of a carbanion from a CH acidic compound...
    2 KB (223 words) - 20:34, 6 August 2020
  • Thumbnail for Diels–Alder reaction
    00131-1. ISBN 978-0-08-052349-1. Grieco, P. A.; Larsen, S. D. (1990). "Iminium Ion-Based Diels–Alder Reactions: N-Benzyl-2-Azanorborene" (PDF). Organic...
    62 KB (7,087 words) - 07:54, 21 July 2024
  • linear acyl derivatives from the nucleophilic abstraction reaction. An iminium ion reacts with a halonium ion formed in situ by reaction of an alkene...
    6 KB (470 words) - 05:54, 14 August 2024
  • Thumbnail for Indane-1,2,3-trione
    Schiff base. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, generally being yellow–orange. "Indan-1,2...
    2 KB (134 words) - 21:22, 4 February 2022
  • Thumbnail for Ergine
    aldehyde and condensation with the proximal secondary amine to form an iminium species, which is subsequently reduced to the tertiary amine and yielding...
    23 KB (2,195 words) - 00:08, 18 August 2024
  • Ramirez carbodiphosphorane (Ph3P → C0 ← PPh3), and bis(triphenylphosphine)iminium cation (Ph3P → N+ ← PPh3), all of which exhibit considerably bent equilibrium...
    10 KB (1,313 words) - 13:10, 17 August 2024