29552-58-7Relevant academic research and scientific papers
Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow
Audubert, Clément,Bouchard, Alexanne,Mathieu, Gary,Lebel, Hélène
, p. 14203 - 14209 (2019/01/21)
The chemoselective amination of alkyl bromides and chlorides with aqueous ammonia and hydroxylamine was achieved in continuous flow to produce primary ammonium salts and hydroxylamines in high yields. An in-line workup was designed to isolate the corresponding primary amine, which was also telescoped in further reactions, such as acylation and Paal-Knorr pyrrole synthesis. Monosubstituted epoxides are also compatible with the reaction conditions.
EFFECT OF THE STRUCTURE OF AMINES ON RATE AND MECHANISM OF THEIR REACTIONS WITH 2-(β,β-DIBROMOVINYL)-5-NITROFURAN IN ACETONITRILE
Kravchenko, V. V.,Kotenko, A. A.,Popov, A. F.,Kostenko, L. I.,Vegh, D.,Kovac, J.
, p. 2140 - 2143 (2007/10/02)
The kinetics of the reaction of 2-(β,β-dibromovinyl)-5-nitrofuran with alkylamines of various types (primary, secondary, and tertiary) in acetonitrile at 55 deg C were studied.It was shown that enamines are formed quantitatively in the case of the reactions with secondary amines.At the same time the products from the reactions with primary amines are the corresponding amidines.Here the monosubstitution product is formed at the first stage, as in the case of the reactions with secondary amines, and rearranges to the imidoyl halide with subsequent substitution of the halogen atom at the imidoyl carbon atom.A quantitative assessment is made of the effect of the structure of the enamine on the rate of the processes.
KINETICS AND MECHANISM OF REACTION OF AMINES WITH β-BROMOPROPIOPHENONE
Popov, A. F.,Piskunova, Z.,Matvienko, V. N.
, p. 1299 - 1302 (2007/10/02)
The reaction of β-bromopropiophenone with different amines in acetonitrile at 25 deg C was studied.It was found that in the case of primary and secondary amines, the end products of the reaction are β-aminopropiophenones, which form via the intermediate phenyl vinyl ketone.In the case of tertiary amines, the reaction ends at the stage of the formation of phenyl vinyl ketone.The reactivity of the amines in the formation of phenyl vinyl ketone is preferentially determined by their basicity.
KINETICS OF THE REACTIONS OF 2-HALOGENOPYRIDINIUM SALTS WITH PRIMARY AND SECONDARY AMINES IN ACETONITRILE
Litvinenko, L. M.,Titskii, G. D.,Mitchenko, E. S.
, p. 1731 - 1736 (2007/10/02)
The kinetics of the reactions of 2-halogeno-N-alkylpyridinium salts with primary and secondary aliphatic amines in acetonitrile at 25 deg C were investigated.The reactions obey second-order relationships.In the reaction of 2-bromo-N-ethylpyridinium bromide with aliphatic amines the effect of electronic and steric factors on the reactivity of the amines was examined.
The Stabilisation of P(NH2)Hal2 (Hal = Cl, Br, I) and P(NHMe)2Cl as Complex Ligands
Maisch, Hartmut
, p. 61 - 67 (2007/10/02)
The phosphanes P(NH2)Hal2 and P(NHMe)2Cl are stabilised as ligands in (CO)5MoP(NH2)Hal2 and (CO)5MoP(NHMe)2Cl (10) by reactions of (CO)5MoP(NH2)3 (1) with HHal or of (CO)5MoP(NHMe)3 (8) with HCl, respectively. 4 decomposes at room temperature and reacts with t-BuNH2 to give (CO)5MoP(NH-t-Bu)2NH2 (6). 1 and HI form (CO)5MoPI3. 3 can also be prepared from 2 with HBr, 4 from 2 and 3 with HBr and HI, respectively.The reactions of 2-4 with NR3 produce polymers, whereas the reaction of 3 with pyridine leads to (CO)5MoNC5H5.The mixtures (CO)5MoP(NH Me)Br2/(CO)5MoPBr3 and (CO)5MoP(NH-i-Pr)2Cl/(CO)5MoP(NH-i-Pr)Cl2 are isolated from reactions of 8 with HBr and of 9 with HI, and 9 reacts with HBr to give (CO)5MoPBr3. (CO)5MoP(NHMe)I2 is formed in small amounts by the reaction of 8 with HI, the main product is an insoluble solid, which is probably the impure intermediate (2+)*2I(1-).Reaction of 10 with NEt3 leads to the formation of the dinuclear complex 12 in which the new diazadiphosphetidine 2 functions as a bridging ligand between two (CO)5Mo units. - Keywords: Ligand Reactions, Hydrogen Halides, Phosphanes
