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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 ...
This reaction is also called the Regitz diazo transfer. [7] Examples are the synthesis of tert-butyl diazoacetate [ 8 ] and diazomalonate. [ 9 ] Methyl phenyldiazoacetate is generated in this way by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base.
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 ...
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 ).
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.
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:
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.