10129-44-9Relevant articles and documents
Flow-Assisted Synthesis of Bicyclic Aziridines via Photochemical Transformation of Pyridinium Salts
Siopa, Filipa,António, Joao P. M.,Afonso, Carlos A. M.
, p. 551 - 556 (2018)
Herein is described the development and comparison of homemade continuous-flow reactors, a fluorinated ethylene propylene tube (FEP) reactor (internal diameter of 0.4 cm) and two parallel quartz reactors containing two different internal diameters (0.4 and 0.2 cm), and their application to the photochemical transformation of 1-n-butyl- and 1-allylpyridinium bromide salts (1a and 1b, respectively) to the corresponding α-hydroxycyclopentenoaziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) 2a and 2b. Under recirculating conditions, the FEP reactor allowed the production of a greater quantity of bicyclic aziridine (3.2 g), while the quartz reactor with the same diameter furnished the best productivity results (3.7 g L-1 h-1). In addition, the FEP reactor operated efficiently under circulating conditions (1.75 L of 1a) for 4.5 days (residence time of 17.9 h), allowing the production of 2a at a rate of 2 g/day (62-93% conversion).
Spectroscopic study of reaction of propargyl bromide with pyridine
Kanitskaya,Elokhina,Fedorov,Shulunova,Nakhmanovich,Turchaninov,Lopyrev
, p. 778 - 784 (2002)
Pyridine was reacted with propargyl bromide to obtain the dibromide [C 5H5NCH=CHCH=CHCH=CHC5H5N] 2+ 2Br-. The effect of the vinyl group on its UV spectrum is qualitatively interpreted using the results of nonempirical quantum-chemical calculations (basis HF/6-31G*).
Dynamic Covalent Chemistry of Nucleophilic Substitution Component Exchange of Quaternary Ammonium Salts
Kulchat, Sirinan,Lehn, Jean-Marie
, p. 2484 - 2496 (2015/11/02)
Dynamic covalent libraries (DCLs) of quaternary ammonium cations were set up by reversible nucleophilic substitution (SN2′ and SN2) exchange reactions of ammonium salts and tertiary amines. The reactions were conducted at 60 °C to generate thermodynamically and kinetically controlled mixtures of quaternary ammonium compounds and tertiary amines, and were accelerated by using iodide as a nucleophilic catalyst. Microwave irradiation was used to assist the exchange reaction between the pyridinium salts and pyridine derivatives. Finally, experiments towards the generation of dynamic ionic liquids were performed. The results of this study pave the way for the extension of dynamic combinatorial chemistry to nucleophilic substitution reactions.
Nitrogen-containing ionic liquids: Biodegradation studies and utility in base-mediated reactions
Ford, Leigh,Ylijoki, Kai E.O.,Garcia, M. Teresa,Singer, Robert D.,Scammells, Peter J.
, p. 849 - 857 (2015/06/23)
Several ionic liquids (ILs) were prepared in order to study the susceptibility of various cores and substituents to biodegradability using the 'CO2 headspace' test (ISO 14593). Several of the ILs contained tertiary amine substituents and were tested as solvents and reagents for several base mediated processes including Suzuki-Miyaura, Sonogashira, Knoevenagel, and Morita-Baylis-Hilman reactions. It was found that although these ILs contain basic functionality, they do not promote base mediated reactions. Density functional theory molecular calculations confirmed that the protonation of these ILs is energetically unfavourable. Journal compilation