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Protodeboronation is a well-known undesired side reaction, and frequently associated with metal-catalysed coupling reactions that utilise boronic acids (see Suzuki reaction). [1] For a given boronic acid, the propensity to undergo protodeboronation is highly variable and dependent on various factors, such as the reaction conditions employed and ...
The reaction is named after pinacol (also known as 2,3-dimethyl-2,3-butanediol or tetramethylethylene glycol), which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859.
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction .
The reaction product he obtained instead he called paraceton which he believed to be an acetone dimer. In his second publication in 1860 he reacted paraceton with sulfuric acid (the actual pinacol rearrangement). Again Fittig was unable to assign a molecular structure to the reaction product which he assumed to be another isomer or a polymer.
It has the formula [(CH 3) 4 C 2 O 2 B] 2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B 2 pin 2. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis.
This page contains tables of azeotrope data for various binary and ternary mixtures of solvents. The data include the composition of a mixture by weight (in binary azeotropes, when only one fraction is given, it is the fraction of the second component), the boiling point (b.p.) of a component, the boiling point of a mixture, and the specific gravity of the mixture.
Bromobenzaldehyde isomers Common name and systematic name 2-Bromobenzaldehyde [1] 3-Bromobenzaldehyde [2] 4-Bromobenzaldehyde [3] [4] Structure Molecular formula: C 7 H 5 BrO (BrC 6 H 4 COH) Molar mass: 185.020 g/mol Appearance colorless liquid colorless liquid white solid CAS number [6630-33-7] [3132-99-8] [1122-91-4] Properties Density and ...
Similarly it gives boronic acid esters, which can be useful in the cross coupling reactions. [3] [4] A condensation reaction of neopentyl glycol with 2,6-di-tert-butylphenol gives CGP-7930. Neopentyl glycol is a precursor to Neopentyl glycol diglycidyl ether. The sequence begins with alkylation with epichlorohydrin using a Lewis acid catalyst.