Favorskii reaction

Favorskii reaction

The Favorskii reaction (not to be confused with the Favorskii rearrangement), named for the Russian chemist Alexei Yevgrafovich Favorskii , is a special case of nucleophilic attack on a carbonyl group involving a terminal alkyne with acidic protons. [M. Smith, J. March, "March's advanced organic chemistry", Wiley-Interscience, 2001]

When catalyzed by acid, this reaction is called the Meyer-Schuster rearrangement.

Reaction mechanism

A metal acetylide is formed in situ when an alkyne is treated with a strong bases such as a hydroxide or an alkoxide. The metal acetylide then reacts with an aldehyde or ketone to form a propargyl alcohol. When an alpha hydrogen is present (as is the case when the carbonyl is an aldehyde), it will tautomerize to the corresponding enone.

This reaction is used as a protect alkynes: the alkyne is either converted with acetone to a 2-hydroxyprop-2-yl-alkyne or converted directly with the commercially available 3-methyl-1-butyne-3-ol also to a protected alkyne. The protective group can be removed by heating the compound in a solution of potassium hydroxide in isopropanol (a retro-Favorskii reaction). [T. Greene, P. Wuts, "Protective groups in organic synthesis", Wiley-Interscience, 1998]

References


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать реферат

Look at other dictionaries:

  • Favorskii rearrangement — The Favorskii rearrangement (not to be confused with the Favorskii reaction), named for the Russian chemist Alexei Yevgrafovich Favorskii , is most principally a rearrangement of cyclopropanones and α halo ketones which leads to carboxylic acid… …   Wikipedia

  • Réaction de réarrangement — Les réactions de réarrangement (ou réactions de transposition) forment une classe de réactions organiques dans lesquelles le squelette carboné d une molécule subit un réarrangement pour donner un isomère de constitution[1]. La plupart du temps,… …   Wikipédia en Français

  • Alexei Yevgrafovich Favorskii — Infobox Scientist name = Alexei Yevgrafovich Favorskii image width = caption = Alexei Yevgrafovich Favorskii birth date = birth date|1850|2|20 birth place = Pavlovo, in the Nizhny Novgorod Oblast, Russia residence = nationality = flag|Russia|name …   Wikipedia

  • Ring expansion reaction — A ring expansion reaction is a type of organic reaction in which usually a hydrocarbon ring is expanded. Examples of ring expansions are: * Beckmann rearrangement * Dowd Beckwith ring expansion reaction. Ring contraction reaction A ring… …   Wikipedia

  • Ramberg-Bäcklund reaction — The Ramberg Bäcklund Reaction is an organic reaction converting a α halo sulfone into an alkene in presence of a base with extrusion of sulfur dioxide Ref|Ramberg. The reaction is named after the two Swedish chemists Ludwig Ramberg and Birger… …   Wikipedia

  • List of organic reactions — Well known reactions and reagents in organic chemistry include Contents: A B C D E F G H I J K L M N O P Q R S T U V W X Y Z    See also   Ext …   Wikipedia

  • Список российских химиков — Скульптура в честь Менделеева и его периодической таблицы в Словакии. Список российских химиков, включающих знаменитых химиков из России, Советского Союза и Российской Империи, которые внесли значительный вклад в науку основатели научных школ и… …   Википедия

  • Scientific phenomena named after people — This is a list of scientific phenomena and concepts named after people (eponymous phenomena). For other lists of eponyms, see eponym. NOTOC A* Abderhalden ninhydrin reaction Emil Abderhalden * Abney effect, Abney s law of additivity William de… …   Wikipedia

  • List of Russian chemists — A sculpture in honor of Dmitry Mendeleev and his Periodic table in Slovakia. This list of Russian chemists includes the famous chemists and material scientists of the Russian Federation, the Soviet Union, the Russian Empire and other predecessor… …   Wikipedia

  • List of Russian people — The Millennium of Russia monument in Veliky Novgorod, featuring the statues and reliefs of the most celebrated people in the first 1000 years of Russian history …   Wikipedia

Share the article and excerpts

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