Dialkylamines
Dialkylamines form a group of organic chemical compounds that are derived from ammonia (NH 3 ), of which two of the three hydrogen atoms have been replaced by alkyl radicals R. The dialkylamines are occasionally also called secondary amines . If the radicals R are the same, the dialkylamines have the general formula HNR 2 . A well-known dialkylamine is diisopropylamine [R = CH (CH 3 ) 2 ].
Dialkylamines should not be confused with dialkylamides - more precisely N , N -dialkylamides.
use
The reaction of aldehydes or ketones with secondary amines forms enamines with elimination of water , which are important for the formation of carbon-carbon bonds, as these are easily absorbed by electrophiles (e.g. from acid chlorides and activated alkylating agents such as allyl halides and α- Halocarboxylic acid esters and electron-poor alkenes) react. Diisopropylamine is converted into lithium diisopropylamide (LDA) by reaction with elemental lithium in the presence of styrene .
Dialkylamines react with carbon disulfide to form dithiocarbamic acids.
Dialkylamines react with nitrous acid to form nitrosamines , which are often carcinogenic .
Individual evidence
- ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 2: Cm-G. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1981, ISBN 3-440-04512-9 , p. 923.
- ↑ Eberhard Breitmaier, Günther Jung: Organic chemistry . 7th edition, Thieme Verlag, 2012, ISBN 978-3-13-541507-9 , p. 325.
- ↑ Ludwig Gattermann , Heinrich Wieland : The practice of the organic chemist . ISBN 3-11-006654-8 .
- ↑ Manfred T. Reetz , Wilhelm F. Maier: Simple representation of lithium diisopropylamide on a molar scale . In: Liebig's annals . No. 10, 1980, pp. 1471-1473, doi: 10.1002 / jlac.198019801002 .
- ^ Siegfried Hauptmann : Organic chemistry . 2nd revised edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig 1985, ISBN 3-342-00280-8 , p. 494.