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substrates. Although the highly unstable formyl chloride was initially postulated as an intermediate, formyl cation (i.e., protonated carbon monoxide), , is now thought to react directly with the arene without the initial formation of formyl chloride. Additionally, when zinc chloride is used as the
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co-catalyst is often necessary. The transition metal co-catalyst may server as a "carrier" by first reacting with CO to form a carbonyl complex, which is then transformed into the active electrophile.
359:
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386:
Karrer, P. (1919). "Ăśber
Oxycarbonylverbindungen I. Eine neue Synthese von" [Hydroxycarbonyl compounds. I. A new synthesis of hydroxyaldehydes].
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Lewis acid instead of aluminum chloride for example, or when the carbon monoxide is not used at high pressure, the presence of traces of
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For the conversion of benzenediazonium chloride to a haloarene (also referred to as the 'Gattermann reaction'), see
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Strategic
Applications of Named Reactions in Organic Synthesis : Background and Detailed Mechanisms
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255:
416:; Levine, I. (1923). "Simplification of the Gattermann Synthesis of Hydroxy Aldehydes".
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Fuson, R. C.; Horning, E. C.; Rowland, S. P.; Ward, M. L. (1955). "Mesitaldehyde".
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is a solid, making it safer to work with than gaseous HCN. The Zn(CN)
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Unlike the
Gattermann reaction, this reaction is not applicable to
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451:. New York: John Wiley & Sons, Inc. pp. 38 & 53–54.
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Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
627:"550. The Gattermann–Koch reaction. Part II. Reaction kinetics"
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Name
Reactions: A Collection of Detailed Reaction Mechanisms
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330:(6th ed.), New York: Wiley-Interscience, p. 725,
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reacts with the HCl to form the key HCN reactant and Zn(Cl)
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250:, named after the German chemists Ludwig Gattermann and
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The reaction can be simplified by replacing the HCN/AlCl
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Modifications have shown that it is possible to use
254:, is a variant of the Gattermann reaction in which
596:. Czako, Barbara. Burlington: Elsevier Science.
360:Berichte der deutschen chemischen Gesellschaft
32:Diazonium compound § Gattermann reaction
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258:(CO) is used instead of hydrogen cyanide.
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173:. Although it is also highly toxic, Zn(CN)
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185:that serves as the Lewis-acid catalyst
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129:). It is named for the German chemist
521:"Eine Synthese aromatischer Aldehyde"
7:
687:Carbon-carbon bond forming reactions
100:Gattermann salicylaldehyde synthesis
355:"Synthese aromatischer Oxyaldehyde"
625:Dilke, M. H.; Eley, D. D. (1949).
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162:in place of hydrogen cyanide.
1:
212:Gattermann–Koch formylation
457:10.1002/0471264180.or009.02
449:Organic Reactions, Volume 9
193:method is the synthesis of
114:(HCl) in the presence of a
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500:, vol. 3, p. 549
353:; Berchelmann, W. (1898).
301:Stephen aldehyde synthesis
189:. An example of the Zn(CN)
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539:10.1002/cber.18970300288
492:10.15227/orgsyn.023.0057
400:10.1002/hlca.19190020109
373:10.1002/cber.18980310281
248:Gattermann–Koch reaction
205:Gattermann–Koch reaction
18:Gattermann–Koch reaction
590:Kurti, Laszlo. (2005).
135:Friedel–Crafts reaction
40:Gattermann formylation
667:Substitution reactions
388:Helvetica Chimica Acta
296:Houben–Hoesch reaction
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133:and is similar to the
96:Gattermann formylation
677:Formylation reactions
552:Li, Jie Jack (2003).
447:Adams, Roger (1957).
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235:Substitution reaction
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59:Substitution reaction
639:10.1039/JR9490002613
431:10.1021/ja01663a020
320:Smith, Michael B.;
283:nickel(II) chloride
94:(also known as the
92:Gattermann reaction
682:Addition reactions
526:Chemische Berichte
279:copper(I) chloride
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252:Julius Arnold Koch
225:Julius Arnold Koch
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123:aluminium chloride
603:978-0-08-057541-4
498:Collected Volumes
483:Organic Syntheses
419:J. Am. Chem. Soc.
337:978-0-471-72091-1
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221:Ludwig Gattermann
169:combination with
131:Ludwig Gattermann
112:hydrogen chloride
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49:Ludwig Gattermann
27:Chemical reaction
16:(Redirected from
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73:ontology ID
65:Identifiers
45:Named after
517:Koch, J. A.
272:and phenol
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307:References
199:mesitylene
116:Lewis acid
110:(HCN) and
104:formylated
647:0368-1769
612:850164343
567:Springer
519:(1897).
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324:(2007),
290:See also
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