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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 ...
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 base deprotonates the methylene, yielding an enolate, which reacts with tosylazide and subsequently decomposes in the presence of a weak acid, to give the α-diazo-1,3-diketone. diazo-transfer. The necessary requirement of two electron withdrawing groups makes this reaction one of limited scope.
A solution of the olefinic acid (0.499 g, 2.25 mmol) dissolved in benzene (20 ml, freshly distilled from calcium hydride) was stirred at 0 °C (ice bath) under nitrogen while oxalyl chloride (1.35 ml, 2.0 g, 15.75 mmol) was added dropwise. The ice bath was removed and the solution was stirred at room temperature for 2 hr.
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.
Nitrosation and nitrosylation are two names for the process of converting organic compounds or metal complexes [1] into nitroso derivatives, i.e., compounds containing the R−NO functionality. The synonymy arises because the R-NO functionality can be interpreted two different ways, depending on the physico-chemical environment: