A common explanation of the DMAP acceleration suggests that DMAP, as a stronger nucleophile than the alcohol, reacts with the O -acylisourea leading to a reactive amide ("active ester"). This intermediate cannot form intramolecular side products but reacts rapidly with alcohols.

4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH 3) 2 NC 5 H 4 N. This white solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe 2 substituent.

Alkylation of carboxylic acids with iodomethane (MeI) provides methyl esters. Alkylation with a large variety of electrophiles is possible, making it a useful alternative to Fisher Esterification in some cases. One drawback is the possible alkylation of other nucleophilic sites. [2]

A critical factor for the increased nucleophilicity of the pyridine nitrogen in 4-(dimethylamino)pyridine (DMAP) is electron donation via resonance from the amino group into the aromatic ring that increases electron density on the pyridine nitrogen.

In conclusion, we have developed an efficient protocol for the synthesis of amide derivatives with electron deficient and unreactive amines using EDC, and catalytic amount of HOBt in the presence of DMAP. The use of DMAP is critical for reactivity and …

4-Dimethylaminopyridine (DMAP) is a nucleophilic catalyst used for numerous different reactions. DMAP is a very effective acyl transfer agent. The use of 4-aminopyridines (such a DMAP) has been shown to speed up the esterification of hindered alcohols via …

protecting primary over secondary alcohols. The protecting groups that mask 1,2- and 1,3-diols (forming either the dioxolane or dioxane, respectively) are often referred to (PREFIX)ylidenes, where the prefix depends on the nature of R and R1. cat. Camphor Sulfonic Acid (CSA) and MeOH. Adv./Disadv.: diols. It forms readily and is easily removed.

4-Dimethylaminopyridine | C7H10N2 | CID 14284 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

Nitrites such as sodium nitrite or amyl nitrite oxidise iron in haemoglobin from ferrous to ferric iron, forming methaemoglobin. 4-dimethylaminopyridine (4DMAP) works by a similar mechanism via methaemoglobin.

Mar 2, 2010 · 4-(Dimethylamino)pyridine (DMAP) is a toxic, corrosive solid that is widely used as a nucleophilic catalyst in esterification, hydrosilylation, Bayliss–Hillman reactions, and many more. In 2001, G. C. Fu and co-workers showed that chiral derivatives of DMAP can be used for stereoselective catalysis.