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Wong suggests that the reaction mechanism of the (S)-Cat catalyzed N-nitroso aldol reaction between nitrosobenzene and butanal proceeds via an enol intermediate and not via an enamine intermediate. The view of oxazolidinones as a parasitic species is contested by Seebach and Eschenmoser who in 2007 published an article [ 28 ] in which they ...
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or another electrophilic alkylation reagent to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. [1] Since enamines are generally produced ...
The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another: These products are known as aldols, from the ald ehyde + alcoh ol, a ...
Methyl ketone self-condensation is a side-reaction which can be avoided through the addition of TiCl 4 [12] into the reaction mixture (to act as a water scavenger). [13] [14] An example of an aldehyde reacting with a secondary amine to form an enamine via a carbinolamine intermediate is shown below: Enamine synthesis with a carbinolamine ...
Proline organocatalysis. Proline organocatalysis is the use of proline as an organocatalyst in organic chemistry. This theme is often considered the starting point for the area of organocatalysis, even though early discoveries went unappreciated. [1] Modifications, such as MacMillan’s catalyst and Jorgensen's catalysts, proceed with excellent ...
Depending on reaction conditions, reactive intermediate imines can also undergo attack by amine products to afford secondary and tertiary amines: 2 R-C≡N + 4 H 2 → (R-CH 2) 2 NH + NH 3 3 R-C≡N + 6 H 2 → (R-CH 2) 3 N + 2 NH 3. Such reactions proceed via enamine intermediates. [8]
RXNO:0000335. Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amines and is widely used in green chemistry since it can be done ...
Aldol condensation. An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to give a conjugated enone. The overall reaction equation is as follows (where the ...