63318-20-7Relevant 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.
MECHANISMS OF FREE-RADICAL REACTIONS. XIV. SELECTIVITY OF FREE-RADICAL CHLORINATION OF VALERIC ACID DERIVATIVES WITH ARYLCHLOROIODONIUM CHLORIDES
Dneprovskii, A. S.,Krainyuchenko, I. V.
, p. 324 - 328 (2007/10/02)
The free-radical chlorination of C4H9Y compounds with arylchloroiodonium chlorides was investigated.The reaction of the secondary C-H bonds increases as they become further from the electronegative substituent.The reaction parameters were calculated from the ratio of the β- and γ-monochlorides by means of the Taft equation.The absolute value of ρ increases with the introduction of electronwithdrawing substituents into the arylchloroiodonium chloride molecule.
Chlorination of Esters. I. Chlorination of Methyl Esters of Propanoic, Butanoic, Pentanoic and Hexanoic Acids. The Isomer Distribution of Monochloro Esters Formed
Korhonen, Ilpo O.O.,Korvola, Jorma N.J.
, p. 139 - 142 (2007/10/02)
The chlorination of methyl ester with chlorine in the liquid and vapor phase and with sulfuryl chloride in the liquid phase has been investigated.The chlorination yields all possible monochloro esters isomers with the 2-chloro isomer in the smallest amount.The products were identified by NMR and mass spectrometry.The isomer distribution and mass spectra of products were studied in detail.
