Abstract
The N,N-dibrominated amines easily can be prepared by reaction of the corresponding amines with heterocyclic N-bromo imides. Some properties and reactions are given. As just reported they show a thermal instability. Only three compounds could be prepared in pure critalline state: CH3NBr2 (until now just known as a solution), Br2NCH2CH2NBr2 and (CH3)3CNBr2. The last one shows a superior stability and was investigated more exactly.
According to:
for the first time a cristalline N-monobromomonoalkylamine was prepared. Comparison with the acyl derivatives of dibromoamine shows a partly differing behaviour of the alkyl derivatives, which is explained by differences in the polarisation of the N−Br bonding.
Similar content being viewed by others
Literatur
A. W. Hofmann, Ber. dtsch. chem. Ges.16, 558 (1883).
J. Jander undCh. Lafrenz, Z. Anorg. Allgem. Chem.349, 57 (1967).
V. L. Heasley, P. Kovacic undR. M. Lange, J. Org. Chem.,31, 3050 (1966).
Th. Seliwanow, Ber. dtsch. chem. Ges.26, 423 (1893).
N. Kijner, Russ. phys. chem. Ges.31, 1033 (1899); Chem. Zbl.1900 I, 958.
O. Wallach, Ann. Chem.259, 307 (1890).
K. Seppelt undW. Sundermeyer, Z. Naturforsch.B 24, 774 (1969).
W. Gottardi, Mh. Chem.104, 421 (1973).
Siehe auch die folgende Arbeit,W. Gottardi, Mh. Chem.104, 1690 (1973).
Houben-Weyl, Methoden der Organischen Chemie, Bd. 8, 321 (1952).
C. E. Boozer undJ. W. Moncrief, J. Org. Chem.27, 623 (1962).
Sonia Dunstan undH. B. Henbest, J. Chem. Soc.1957, 4905.
R. Willstätter undV. Hottenroth, Ber. dtsch. chem. Ges.37, 1783 (1904).
N. Kijner, J. Prakt. Chem. [2]64, 113 (1901).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Gottardi, W. Dibromamin: Alkylderivate. Monatshefte für Chemie 104, 1681–1689 (1973). https://doi.org/10.1007/BF00909655
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00909655