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Dimethylformamide, DMF is an organic compound with the chemical formula H C O N(CH 3) 2.Its structure is HC(=O)−N(−CH 3) 2.Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids.
The first step is the formation of an enamine 2 using N,N-dimethylformamide dimethyl acetal and pyrrolidine. The desired indole 3 is then formed in a second step by reductive cyclisation. The Leimgruber-Batcho indole synthesis. In the above scheme, the reductive cyclisation is effected by Raney nickel and hydrazine.
Benzyl or tert-butyl acetoacetates also work well in this system, and with close temperature control, the tert-butyl system gives a very high yield (close to 80%). [10] N,N-dialkyl pyrrole-2- and/or 4-carboxamides may be prepared by the use of N,N-dialkyl acetoacetamides in the synthesis.
In enzymology, a N,N-dimethylformamidase (EC 3.5.1.56) is an enzyme that catalyzes the chemical reaction N,N-dimethylformamide + H 2 O ⇌ {\displaystyle \rightleftharpoons } dimethylamine + formate Thus, the two substrates of this enzyme are N,N-dimethylformamide and H 2 O , whereas its two products are dimethylamine and formate .
Directed metallation is not limited to lithium intermediates or even to an ortho preference. In one study [13] it is found that the reaction product of N,N-dimethylaniline with a complex of TMEDA, sodium salt of TMP and di-tert-butylzinc is a meta zincated complex as a stable crystalline compound.
A large scale application of the Ritter reaction is in the synthesis of tert-octylamine, by way of the intermediate formamide.This process was originally described by Ritter in 1948, [11] and an estimated 10,000 tons/y (year: 2000) of this and related lipophilic amines are prepared in this way. [12]
The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
tert-Butyl acetate, t-butyl acetate or TBAc is a colorless flammable liquid with a camphor- or blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners and industrial cleaners. It has recently gained EPA volatile organic compound (VOC) exempt status. [3]