Reimer-Tiemann reaction

Reimer-Tiemann reaction

The Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols.Ref|Reimer1876Ref|Wynberg1960Ref|Wynberg1982Ref|Wynberg1991 The reaction was discoverd by Karl Ludwig Reimer and Ferdinand Tiemann

Reaction mechanism

Chloroform (1) reacts with strong base to form the chloroform carbanion (2), which will quickly alpha-eliminate to give dichlorocarbene (3). Dichlorocarbene will react in the ortho- and para- position of the phenate (5) to give the dichloromethyl substituted phenol (7). After basic hydrolysis, the desired product (9) is formed.

References

# Reimer, K.; Tiemann, F. "Ber." 1876, "9", 824 & 1268 & 1285.
# Wynberg, H. "Chem. Rev." 1960, "60", 169. (Review)
# Wynberg, H.; Meijer, E. W. "Org. React." 1982, "28", 2. (Review)
# Wynberg, H. "Comp. Org. Syn." 1991, "2", 769-775. (Review)
# Russell, A.; Lockhart, L. B. "Organic Syntheses", Coll. Vol. 3, p.463 (1955); Vol. 22, p.63 (1942). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0463 Article] )

See also

* Duff reaction
* Gattermann aldehyde synthesis


Wikimedia Foundation. 2010.

Игры ⚽ Нужен реферат?

Look at other dictionaries:

  • reimer-tiemann reaction — ˈrīmə(r)|tēmən , ēˌmän noun Usage: usually capitalized R&T Etymology: after Karl Reimer 19th century German chemist and Ferdinand Tiemann died 1899 German chemist : either of two similar chemical reactions: a. : a reaction for producing phenolic… …   Useful english dictionary

  • Réaction de Reimer-Tiemann — La réaction de Reimer Tiemann est une réaction organique utilisé pour l ortho formylation de phénols[1],[2],[3],[4] …   Wikipédia en Français

  • Tiemann — is a surname that may refer to: People Daniel F. Tiemann was mayor of New York (1858 to 1860) Ferdinand Tiemann (1866–1899) was a German chemist and discoverer of the Reimer Tiemann reaction Norbert Theodore Tiemann (1924 ) is a Nebraska… …   Wikipedia

  • Réaction de Duff — La réaction de Duff ou formylation aromatique de l hexamine est une réaction de formylation utilisée en chimie organique pour la synthèse du benzaldéhyde à partir de l hexamine (méthénamine) comme source carbonée de formyle[1],[2],[3] …   Wikipédia en Français

  • Tiemann — Cette page d’homonymie répertorie les différents sujets et articles partageant un même nom. Patronymie Marcel Tiemann (1974 ) est un pilote automobile allemand. Mariella Tiemann (1984 ) est une actrice allemande. Michael Tiemann est le vice… …   Wikipédia en Français

  • Ferdinand Tiemann — Infobox Scientist name = Johann Karl Wilhelm Ferdinand Tiemann image width = caption = Ferdinand Tiemann birth date = birth date|1848|6|10 birth place = Rübeland part of Elbingerode, Germany residence = nationality = death date = death date and… …   Wikipedia

  • Duff reaction — The Duff reaction or hexamine aromatic formylation is a formylation reaction used in organic chemistry for the synthesis of benzaldehydes with hexamine as the formyl carbon source.[1][2][3][4][5] …   Wikipedia

  • Formylation reaction — A formylation reaction in organic chemistry is the catch all name for any organic reaction in which an organic compound is functionalized with a formyl group ( CH=O). Aromatic formylation reactions via electrophilic aromatic substitution include …   Wikipedia

  • Dakin oxidation — The Dakin oxidation The Dakin oxidation is an organic redox reaction in which an ortho or para hydroxylated phenyl aldehyde (2 hydroxybenzaldehyde or 4 hydroxybenzaldehyde) or ketone reacts with hydrogen pero …   Wikipedia

  • Dichlorocarbene — Dichlorocarbene …   Wikipedia

Share the article and excerpts

Direct link
… Do a right-click on the link above
and select “Copy Link”