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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 salts can be reduced with stannous chloride (SnCl 2) to the corresponding hydrazine derivatives. This reaction is particularly useful in the Fischer indole synthesis of triptan compounds and indometacin. The use of sodium dithionite is an improvement over stannous chloride since it is a cheaper reducing agent with fewer environmental ...
In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds or diazoalkanes [a] and are described by the general structural formula R 2 C=N + =N −.
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.
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 ...
Aliphatic alcohols give azides via a variant of the Mitsunobu reaction, with the use of hydrazoic acid. [1] Hydrazines may also form azides by reaction with sodium nitrite: [16] Alcohols can be converted into azides in one step using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) [17] or under Mitsunobu conditions [18] with diphenylphosphoryl azide (DPPA).
In aqueous solution, the nitrogen dioxide also disproportionates, for a net reaction producing nitric oxide and nitric acid: [4]: 1 [5] 3 HNO 2 → 2 NO + HNO 3 + H 2 O Consequently applications of nitrous acid usually begin with mineral acid acidification of sodium nitrite .
Nitrosation is typically performed with nitrous acid, formed from acidification of a sodium nitrite solution. Nitrous acid is unstable, and high yields require a rapid reaction rate. NO + synthon transfer is catalyzed by a strong nucleophile, such as (in order of increasing efficacy) chloride, bromide, thiocyanate, or thiourea.