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The general structure of an imine. In organic chemistry, an imine (/ ɪ ˈ m iː n / or / ˈ ɪ m ɪ n /) is a functional group or organic compound containing a carbon–nitrogen double bond (C=N). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds.
General structure of an imine. Schiff bases are imines in which R 3 is an alkyl or aryl group (not a hydrogen). R 1 and R 2 may be hydrogens General structure of an azomethine compound. In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure R 1 R 2 C=NR 3 (R 3 = alkyl or aryl, but not hydrogen).
Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich. [2] [3] Scheme 1 – Ammonia or an amine reacts with formaldehyde and an alpha acidic proton of a carbonyl compound to a beta amino carbonyl compound.
The Staudinger synthesis, also called the Staudinger ketene-imine cycloaddition, is a chemical synthesis in which an imine 1 reacts with a ketene 2 through a non-photochemical 2+2 cycloaddition to produce a β-lactam 3. [1] The reaction carries particular importance in the synthesis of β-lactam antibiotics. [2]
Amine. In chemistry, amines (/ ə ˈ m iː n, ˈ æ m iː n /, [1] [2] UK also / ˈ eɪ m iː n / [3]) are compounds and functional groups that contain a basic nitrogen atom with a lone pair.Formally, amines are derivatives of ammonia (NH 3 (in which the bond angle between the nitrogen and hydrogen is 170°), wherein one or more hydrogen atoms have been replaced by a substituent such as an ...
The first N-sulfinyl imines in racemic form were formed by oxidation of p-toluene-sulfenyl imines with m-CPBA. [9] Enantiopure p-toluene-sulfinyl imines arise by the reaction of the commercially available Andersen reagent (menthyl p-toluenesulfinate) [10] with metallo-ketimines but is limited to ketone derived N-sulfinyl imines. [11]
In organic chemistry, a semicarbazone is a derivative of imines formed by a condensation reaction between a ketone or aldehyde and semicarbazide. They are classified as imine derivatives because they are formed from the reaction of an aldehyde or ketone with the terminal -NH 2 group of semicarbazide, which behaves very similarly to primary amines.
The formic acid acts as a source of hydride and reduces the imine to a secondary amine. Loss of carbon dioxide gas renders the reaction irreversible. Despite being more hindered, the formation of the tertiary amine is more favorable, as the intermediate in iminium ion is formed without needing to protonate.