6263-00-9Relevant academic research and scientific papers
New method for the preparation of N-chloroamines by oxidative N-halogenation of amines using oxone-KCl
Sriramoju, Vinodkumar,Kurva, Srinivas,Madabhushi, Sridhar
supporting information, p. 699 - 704 (2018/02/16)
A mild and efficient method for preparation of N-chloroamines by oxidative N-halogenation of primary/secondary amines using oxone-KCl is described.
A Mechanochemical-Assisted Oxidation of Amines to Carbonyl Compounds and Nitriles
Gaspa, Silvia,Porcheddu, Andrea,Valentoni, Antonio,Garroni, Sebastiano,Enzo, Stefano,De Luca, Lidia
supporting information, p. 5519 - 5526 (2017/09/06)
A mild, efficient, metal- and solvent-free oxidation of primary amines to aldehydes, ketones, and nitriles under ball-milling conditions is presented. This method has proved to be compatible with various functional groups and only requires easily accessible starting materials. Simple purification of the reaction mixtures by short-column chromatography afforded pure aldehydes, ketones, and nitriles as products.
The N-chlorination of primary amines using FeCl3 and m-CPBA
Liu, Jia,Xu, Junchao,Ren, Jiangmeng,Zeng, Bu-Bing
supporting information, p. 190 - 192 (2014/03/21)
A simple and effective method for the synthesis of N,Ndichloroamines from primary amines was conducted successfully with m-CPBA as oxidant and FeCl 3 as chlorine source at 0 °C. Moreover, N,N-dichloroamines could be converted into nitriles or N-chloroimines in good yields.
Poly(N,N′-dichloro-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide as novel reagents for the synthesis of N-chloroamines, nitriles and aldehydes
Ghorbani-Vaghei, Ramin,Veisi, Hojat
experimental part, p. 945 - 950 (2009/12/01)
The applications of poly(N,N′-dichloro-N-ethylbenzene-1,3- disulfonamide) (PCBS) and N,N,N′,N′-tetrachlorobenzene-1,3- disulfonamide (TCBDA) as novel reagents for the preparation of N,N-dichloroamines, nitriles, and aldehydes from primary amines under various conditions are described. Also, a simple and effective procedure for the direct oxidative conversion of primary alcohols into nitriles was successfully carried out with TCBDA and PCBS in aqueous ammonia. Georg Thieme Verlag Stuttgart.
Kinetic and thermodynamic barriers to chlorine transfer between amines in aqueous solution
Calvo, Paula,Crugeiras, Juan,Rios, Ana
experimental part, p. 5381 - 5389 (2009/12/03)
(Chemical Equation Presented) Third-order rate constants for the acid-catalyzed reversible reaction of N-chlorotaurine with benzylamine and dimethylamine were determined in water at 25°C and I = 0.5 (NaClO 4). The reaction with benzylamine shows inverse solvent deuterium isotope effects of kH/kD = 0.57 and 0.47 in the forward and reverse directions, respectively. These isotope effects, together with the absence of detectable general acid catalysis for this reaction, provide evidence for a stepwise mechanism involving fast equilibrium protonation of N-chlorotaurine followed by rate-determining chlorine transfer from the protonated chloramine to benzylamine. The observation of strong catalysis by general acids of the reaction of dimethylamine with N-chlorotaurine suggests a change to a concerted mechanism with proton and chlorine transfer occurring in a single step. This change in mechanism is enforced by the absence of a significant lifetime for protonated chlorotaurine in contact with this strongly nucleophilic amine. The kinetic and thermodynamic parameters for the reaction between protonated chlorotaurine and benzylamine are used to estimate a Marcus intrinsic reaction barrier of ΔG0? = 4.1 kcal/mol for chlorine transfer between amines. Comparison of this intrinsic barrier with those reported previously for bromine transfer between carbanions points to the existence of certain similarities between halogen and proton transfer reactions.
An insight of the reactions of amines with trichloroisocyanuric acid
De Luca, Lidia,Giacomelli, Giampaolo
, p. 2180 - 2184 (2007/10/03)
The reaction between amines or α-aminoacids with trichloroisocyanuric acid is studied under various conditions: N,N-dichloroamines, nitriles and ketones can be obtained from primary amines, while free aminoacids undergo oxidative decarboxylation to the corresponding nitrile of one less carbon atom.
Pyrolytic Eliminations from N,N-Dichloro Derivatives of Primary, Secondary, and Tertiary Alkyl Primary Amines
Roberts, John T.,Rittberg, Barry R.,Kovacic, Peter
, p. 4111 - 4115 (2007/10/02)
N,N-Dichloro derivatives of primary, secondary, and tertiary alkyl primary amines are easily converted to elimination products by neat or solution pyrolysis during GLC at 190-280 deg C.Good to excellent yields result.In general, the type of product formed depends on the alkyl group: with primary alkyl, the products are alkenes and nitriles; with secondary, alkenes and chloroimines result; and with tertiary types, alkenes are formed.Mechanistic aspects are treated.
