Pinacol
Encyclopedia
Pinacol is a white solid organic compound.
from acetone
:
-diol, it can rearrange to pinacolone
by the pinacol rearrangement
, e.g. by heating with sulfuric acid
:
Pinacol can be use with borane and boron trichloride to produce useful synthetic intermediate such as pinacolborane, bis(pinacolato)diboron
, and pinacolchloroborane.
Preparation
It may be produced by the pinacol coupling reactionPinacol coupling reaction
A pinacol coupling reaction is an organic reaction in which a carbon–carbon covalent bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process . The reaction product is a vicinal diol...
from acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
:
Reactions
As a vicinalVicinal (chemistry)
In chemistry vicinal stands for any two functional groups bonded to two adjacent carbon atoms. For example the molecule 2,3-dibromobutane carries two vicinal bromine atoms and 1,3-dibromobutane does not....
-diol, it can rearrange to pinacolone
Pinacolone
Pinacolone is an important ketone in organic chemistry. It has an odour reminiscent of peppermint and was discovered in 1866...
by the pinacol rearrangement
Pinacol rearrangement
The pinacol rearrangement or pinacol-pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. This 1,2-rearrangement takes place under acidic conditions...
, e.g. by heating with sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
:
Pinacol can be use with borane and boron trichloride to produce useful synthetic intermediate such as pinacolborane, bis(pinacolato)diboron
Bis(pinacolato)diboron
Bisdiboron is a boron containing two pinacolato ligands. This compound may be prepared by reacting tetrakisdiboron with pinacol in acidic conditions. This compound is a commercially-available starting material useful for making Pinacol boronic esters for organic synthesis....
, and pinacolchloroborane.