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Methyldiazonium is an organic compound consisting of a methyl group attached to a diazo group.This cation is the conjugate acid of diazomethane, with an estimated pK a <10. [1]It is an intermediate in methylation reactions of diazomethane with acidic hydroxyl compounds, such as conversion of carboxylic acids to methyl esters and phenols to methyl ethers.
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N + ≡N]X − where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent compound where R is hydrogen, is diazenylium.
The reaction process begins with diazotization of the amine by nitrous acid. The diazonium group is a good leaving group, forming nitrogen gas when displaced from the organic structure. This displacement can occur via a rearrangement (path A), in which one of the sigma bonds adjacent to the diazo group migrates. This migration results in an ...
In diazo transfer certain carbon acids react with tosyl azide in the presence of a weak base like triethylamine or DBU. The byproduct is the corresponding tosylamide (p-toluenesulfonamide). This reaction is also called the Regitz diazo transfer. [7] Examples are the synthesis of tert-butyl diazoacetate [8] and diazomalonate. [9]
The resonating arrow (1) shows a resonance contributor of the diazo compound with a lone pair of electrons on the carbon adjacent to the nitrogen. The diazo compound then does a nucleophilic attack on the carbonyl-containing compound ( nucleophilic addition ), producing a tetrahedral intermediate ( 2 ).
Transannular insertions, which form fused carbocyclic products, have also been observed. Yields are often low for these reactions, however. [15] (8) Insertion into carbon–carbon bonds has been observed. In the example in equation (9), the methyl group is held in close proximity to the diazo group, facilitating C-C insertion. [14] (9)
These reactions entail diazotization of aminocyclobutanes and aminocyclopropanes. Loss of N 2 from the diazo cations results in secondary carbocations, which tend to rearrange and then undergo hydrolysis. The reaction converts aminocyclobutane into a mixture of hydroxycyclobutane and hydroxymethylcyclopropane.
In organic chemistry, an azo coupling is an reaction between a diazonium compound (R−N≡N +) and another aromatic compound that produces an azo compound (R−N=N−R’).In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon (usually from an arene, which is called coupling agent), serves as a nucleophile.