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In the reaction, thermal or photochemical decomposition of N-halogenated amine 1 in the presence of a strong acid (concentrated sulfuric acid or concentrated CF 3 CO 2 H) generates a nitrogen radical intermediate. The radical then abstracts an intramolecular hydrogen atom to give a cyclic amine 2 (pyrrolidine or, in some cases, piperidine).
However, there also have been reported examples of base-free Stieglitz rearrangements of N-halogenated amines. An example for that can be found in the total synthesis of (±)-lycopodine by Paul Grieco et al. [6] [29] There, a ring formation takes place by a rearrangement on a secondary haloamine by subjecting it to silver tetrafluoroborate. [6]
N,N-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist Siegfried Hünig . It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA, DIEA, or i-Pr 2 NEt.
For example, reaction of 1-bromooctane with ammonia yields almost equal amounts of the primary amine and the secondary amine. [3] Therefore, for laboratory purposes, N-alkylation is often limited to the synthesis of tertiary amines. An exception is the amination of alpha-halo carboxylic acids that do permit synthesis of primary amines with ...
Download as PDF; Printable version; In other projects Wikimedia Commons; ... Pages in category "Tertiary amines" The following 96 pages are in this category, out of ...
By reaction with tertiary amines, long-chain alkyl bromides such as 1-bromododecane, give quaternary ammonium salts, which are used as phase transfer catalysts. [ 9 ] With Michael acceptors the addition is also anti-Markovnikov because now a nucleophilic X − reacts in a nucleophilic conjugate addition for example in the reaction of HCl with ...
Tertiary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations). Red highlighted central atoms in various groups of chemical compounds.
Because primary and secondary amines react with aldehydes and ketones, the most common variety of these aminocarbonyl compounds feature tertiary amines. Such compounds are produced by amination of α-haloketones and α-haloaldehydes. [1] Examples include cathinones, methadone, molindone, pimeclone, ferruginine, and tropinone.