Meerwein-Ponndorf-Verley reduction
- Meerwein-Ponndorf-Verley reduction
The Meerwein-Ponndorf-Verley Reduction in organic chemistry is the reduction of ketones to secondary alcohols with aluminumisopropylate catalysis in isopropanol solution [Alexander R. Surrey, Name Reactions in Organic Chemistry, 2nd Edition, Academic Press, 1961.] [Kurti and Czako, Strategic Application of Named Reaction in Organic Synthesis, Elsevier Academic Press, 2005.] .
Reduction of a ketone 1 to the alcohol 3 in the presence of aluminumisopropylate 2.
First the carbonyl-oxygen coordinates to the aluminumisopropylate 2. This makes the carbonyl-carbon even more positive. In the next step the hydride attacks the carbonyl-carbon and a 6-membered cyclic transition state is formed. After the hydride shift the alcoholate of the desired alcohol 5 and acetone 6 remain. The alcoholate reacts with another isopropanol molecule to form the alcohol 3 and recover the Aluminumisopropylate.
All of these reactions are reversible, and complete conversion can be achieved by employing excess alcohol as the reaction solvent or by removal of acetone from the reaction mixture by distillation.
The same process in the opposite direction is called Oppenauer oxidation.
References
*cite journal
title = Ein neues Verfahren zur Reduktion von Aldehyden und Ketonen
author = Hans Meerwein, Rudolf Schmidt
journal = Justus Liebigs Annalen der Chemie
volume = 444
issue = 1
pages = 221 - 238
year = 1924
url =
doi = 10.1002/jlac.19254440112
*cite journal
title = Der reversible Austausch der Oxydationsstufen zwischen Aldehyden oder Ketonen einerseits und primären oder sekundären Alkoholen anderseits
author = Wolfgang Ponndorf
journal = Angewandte Chemie
volume = 39
issue = 5
pages = 138-143
year = 1926
url =
doi = 10.1002/ange.19260390504
*cite journal
title =
author = Verley, A.,
journal = Bull. Soc. Chim. Fr.
volume = 37
issue =
pages = 537
year = 1925
url =
doi =
*cite journal
title = Mechanism of the Meerwein–Ponndorf Reduction
author = L. M. Jackman; J. A. Mills
journal = Nature
volume = 164
issue =
pages = 789-790
year = 1949
url =
doi = 10.1038/164789a0
Wikimedia Foundation.
2010.
Look at other dictionaries:
Meerwein–Ponndorf–Verley reduction — The Meerwein Ponndorf Verley (MPV) Reduction in organic chemistry is the reduction of ketones and aldehydes to their corresponding alcohols utilizing aluminumalkoxide catalysis in the presence of a sacrificial alcohol[1]. The beauty in the MPV… … Wikipedia
Hans Meerwein — Infobox Scientist name = Hans Meerwein box width = image width = caption = birth date = birth date|1879|5|20 birth place = Hamburg, Germany death date = death date and age|1965|10|24|1879|5|20 death place = Marburg, Germany residence = Germany… … Wikipedia
Carbonyl reduction — synthesis of an alcohol by ester reduction Carbonyl reduction in organic chemistry is the organic reduction of any carbonyl group containing compound by a reducing agent. Typical carbonyl compounds are ketones , aldehydes, carboxylic acids and… … Wikipedia
Oppenauer oxidation — Oppenauer oxidation, named after Rupert Viktor Oppenauer,[1] is a gentle method for selectively oxidizing secondary alcohols to ketones. The reaction is the opposite of Meerwein Ponndorf Verley reduction. The alcohol is oxidized with aluminium… … 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
Химические свойства спиртов — Химические свойства спиртов это химические реакции спиртов во взаимодействии с другими веществами. Они определяются в основном наличием гидроксильной группы и строением углеводородной цепи, а также их взаимным влиянием: Чем больше… … Википедия
Aluminium isopropoxide — Chembox new Name = Aluminium isopropoxide ImageFile = Al4(OiPr)12.png ImageName = One enantiomorph of Al4(OiPr)12 IUPACName = Aluminium Isopropoxide OtherNames = Triisopropoxyaluminium Aluminium isopropanolate Aluminium sec propanolate Aluminium… … Wikipedia
Organic redox reaction — Organic redox reactions: The Birch reduction Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from… … Wikipedia
Alcohol — This article is about the generic chemistry term. For the kind of alcohol found in alcoholic beverages, see Ethanol. For beverages containing alcohol, see Alcoholic beverage. For other uses, see Alcohol (disambiguation) … Wikipedia
Transfer hydrogenation — is the addition of hydrogen (H2; dihydrogen in inorganic and organometallic chemistry) to a molecule from a source other than gaseous H2. It is applied in industry and in organic synthesis, in part because of the inconvenience and expense of… … Wikipedia
