Kiến thức

Gattermann reaction-Wikipedia

Gattermann reaction

From Wikipedia, the free encyclopedia

Jump to navigation

Jump to search

Gattermann formylation
Named after

Ludwig Gattermann

Reaction type

Substitution reaction

Identifiers

RSC

ontology ID

RXNO:0000139

The Gattermann reaction, (also known as the Gattermann formylation and the Gattermann salicylaldehyde synthesis) is a chemical reaction in which aromatic compounds are

formylated

by a mixture of

hydrogen cyanide

(HCN) and

hydrogen chloride

(HCl) in the presence of a

Lewis acid

catalyst

such as

AlCl3

. It is named for the German chemist

Ludwig Gattermann

[1]

and is similar to the

Friedel–Crafts reaction

.

Gattermann I.png

Gattermann II.png

The reaction can be simplified by replacing the HCN/AlCl3 combination with

zinc cyanide

.

[2]

Although it is also highly toxic, Zn(CN)2 is a solid, making it safer to work with than gaseous HCN.

[3]

The Zn(CN)2 reacts with the HCl to form the key HCN reactant and Zn(Cl)2 that serves as the Lewis-acid catalyst in-situ. An example of the Zn(CN)2 method is the synthesis of

mesitaldehyde

from

mesitylene

.

[4]

Bạn đang xem: Gattermann reaction-Wikipedia

Gattermann–Koch reaction[

edit

]

Gattermann–Koch formylation
Named after

Ludwig Gattermann

Julius Arnold Koch

Reaction type

Substitution reaction

The Gattermann–Koch reaction, named after the German chemists Ludwig Gattermann and

Julius Arnold Koch

,

[5]

is a variant of the Gattermann reaction in which

carbon monoxide

(CO) is used instead of hydrogen cyanide.

[6]

Gattermann-Koch.svg

Unlike the Gattermann reaction, this reaction is not applicable to

phenol

and phenol

ether

substrates.

[3]

Although the highly unstable formyl chloride was initially postulated as an intermediate, formyl cation (i.e., protonated carbon monoxide), [HCO]+, is now thought to be react directly with the arene without the initial formation of formyl chloride.

[7]

Additionally, when zinc chloride is used as the Lewis acid instead of aluminum chloride for example, or when the carbon monoxide is not used at high pressure, the presence of traces of

copper(I) chloride

or

nickel(II) chloride

co-catalyst is often necessary. The transition metal co-catalyst may server as a “carrier” by first forming reacting with CO to form a carbonyl complex, which is then transformed into the active electrophile.

[8]

See also[

edit

]

  • Houben–Hoesch reaction

  • Stephen aldehyde synthesis

References[

edit

]

  1. ^

    Gattermann, L.; Berchelmann, W. (1898).

    “Synthese aromatischer Oxyaldehyde”

    .

    Berichte der deutschen chemischen Gesellschaft

    . 31 (2): 1765–1769.

    doi

    :

    10.1002/cber.18980310281

    .

  2. ^

    Adams R.

    ; Levine, I. (1923). “Simplification of the Gattermann Synthesis of Hydroxy Aldehydes”.

    J. Am. Chem. Soc.

    45 (10): 2373–77.

    doi

    :

    10.1021/ja01663a020

    .

  3. ^

    a

    b

    Adams, Roger (1957). Organic Reactions, Volume 9. New York: John Wiley & Sons, Inc. pp. 38 & 53–54.

    doi

    :

    10.1002/0471264180.or009.02

    .

    ISBN

     

    9780471007265

    .

  4. ^

    Fuson, R. C.; Horning, E. C.; Rowland, S. P.; Ward, M. L. (1955). “Mesitaldehyde”.

    Organic Syntheses

    .

    doi

    :

    10.15227/orgsyn.023.0057

    .; Collective Volume, 3, p. 549

  5. ^

    Gattermann, L.; Koch, J. A. (1897).

    “Eine Synthese aromatischer Aldehyde”

    .

    Chemische Berichte

    . 30 (2): 1622–1624.

    doi

    :

    10.1002/cber.18970300288

    .

  6. ^

    Li, Jie Jack (2003).

    Name Reactions: A Collection of Detailed Reaction Mechanisms

    (available on

    Google Books

    ) (2nd ed.).

    Springer

    . p. 157.

    ISBN

     

    3-540-40203-9

    .

  7. ^

    Kurti, Laszlo. (2005).

    Strategic Applications of Named Reactions in Organic Synthesis : Background and Detailed Mechanisms

    . Czako, Barbara. Burlington: Elsevier Science.

    ISBN

     

    978-0-08-057541-4

    .

    OCLC

     

    850164343

    .

  8. ^

    Dilke, M. H.; Eley, D. D. (1949).

    “550. The Gattermann–Koch reaction. Part II. Reaction kinetics”

    . J. Chem. Soc. 0: 2613–2620.

    doi

    :

    10.1039/JR9490002613

    .

    ISSN

     

    0368-1769

    .

Retrieved from “

https://en.wikipedia.org/w/index.php?title=Gattermann_reaction&oldid=1011345775

Chuyên mục: Kiến thức

Related Articles

Trả lời

Email của bạn sẽ không được hiển thị công khai. Các trường bắt buộc được đánh dấu *

Back to top button