2023年1月10日 · The pinacol rearrangement is an acid-promoted rearrangement of 1,2-diols which results in C-O (pi) bond formation with migration of a C-C bond

A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. [1]

The pinacol rearrangement is the acid catalyzed rearrangement of a 1,2-diol into a ketone. It is named after the molecule pinacol, pictured below, the simplest substrate to undergo the reaction. One of the alcohols is protonated to make the leaving group (water) while the other OH participates as the rearrangement promoting group.

The pinacol rearrangement is a reaction of 1,2-diols. It takes place under the influence of strong acids, including mineral acids like sulfuric acid. It can also be brought about via the use of Lewis acids.

The Pinacol rearrangement is an important cationic rearrangement reaction widely used for synthesis. 64 Fittig 65, 64 a was the first to discover that treatment of 2,3-dimethylbutane-2,3-diol with sulfuric acid generated 3,3-dimethylbutan-2-one (pinacolone). This transformation gave rise to the name of the reaction, and was shown to be ...

Each step in this rearrangement is potentially reversible, as demonstrated by the acid catalyzed dehydration of pinacolone (and pinacol) to 2,3-dimethyl-1,3-butadiene under vigorous conditions. Many factors must be considered when analyzing the course of a pinacol rearrangement.

The pinacol–pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. The 1,2-rearrangement takes place under acidic conditions. The name of the rearrangement reaction comes from the rearrangement of pinacol to pinacolone .

Pinacol Coupling Reaction. This reaction involves the reductive homo-coupling of a carbonyl compound to produce a symmetrically substituted 1,2-diol. The first step is single electron transfer of the carbonyl bond, which generates radical ion intermediates that couple via carbon-carbon bond formation to give a 1,2-diol.

2024年8月5日 · The pinacol rearrangement is an intramolecular dehydration reaction of 1,2-diols to pinacolones under acid catalysis. Pinacolones are important intermediates in the organic chemical industry,...

In the conversion that gave its name to this reaction, the acid-catalyzed elimination of water from pinacol gives t -butyl methyl ketone. This reaction occurs with a variety of fully substituted 1,2-diols, and can be understood to involve the formation of a carbenium ion intermediate that subsequently undergoes a rearrangement.