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The general structure of an enamine. An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. [1] [2] Enamines are versatile intermediates. [3] [4] Condensation to give an enamine. [5] The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine.
Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula ((CH 3) 2 N) 2 C=C(N(CH 3) 2) 2, It is a colorless liquid. It is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. [1] One unusual feature of TDAE is that it is a tetra-enamine.
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]
Such reactions proceed via enamine intermediates. [8] The most important reaction condition for selective primary amine production is catalyst choice. [ 1 ] Other important factors include solvent choice, solution pH , steric effects , temperature, and the pressure of hydrogen.
In aqueous solution, the enamine can then be hydrolyzed from the product, making it a small organic molecule catalyst. In a seminal example, proline efficiently catalyzed the cyclization of a triketone: This combination is the Hajos-Parrish reaction [41] [42] [43] Under Hajos-Parrish conditions only a catalytic amount of proline is necessary (3 ...
In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime.
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl (C=O) functional group by formaldehyde (H−CHO) and a primary or secondary amine (−NH 2) or ammonia (NH 3). [1]
3-Dimethylaminoacrolein is an organic compound with the formula Me 2 NC(H)=CHCHO. It is a pale yellow water-soluble liquid. The compound has a number of useful and unusual properties, e.g. it "causes a reversal of the hypnotic effect of morphine in mice" and has a "stimulating effect in humans".