2203-36-3Relevant articles and documents
Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals
McMillan, Alastair J.,Sieńkowska, Martyna,Di Lorenzo, Piero,Gransbury, Gemma K.,Chilton, Nicholas F.,Salamone, Michela,Ruffoni, Alessandro,Bietti, Massimo,Leonori, Daniele
supporting information, p. 7132 - 7139 (2021/03/03)
The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine-tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site-selective chlorination of sp3 C?H bonds. This process exploits the ability of protonated N-chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical-chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H-atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C?H chlorination.
Chlorination of Carboxylic Acid Derivatives. IX. Liquid Phase Chlorination of Aliphatic C2-C8 Alkyl Acetates. EI Mass Spectra of Monochlorinated Esters
Korhonen, Ilpo O. O.
, p. 39 - 46 (2007/10/02)
A series of aliphatic alkyl acetates from ethyl to octyl acetate was chlorinated in the liquid phase in order to obtain monochlorinated products.The chlorination of esters was carried out with chlorine in the liquid phase in the absence and in the presence of benzene and with sulfuryl chloride in the presence of Bz2O2.The products were determined by gas-liquid chromatography and gas-liquid chromatography-mass spectrometry.Chlorination is appreciably deactivated at the 1-position, particularly with SO2Cl2, the deactivation at the 2-position being strongest with Cl2 in the presence of benzene.The amounts of 1-chloro and ω-chloro isomers constituted the greatest disparity between the chlorination methods.The most characteristic mass spectral fragment ions of the 35 chlorinated alkyl acetates are given.