14273-86-0Relevant articles and documents
Cobalt-catalyzed photolytic methoxycarbonylation of bromoalkanes in the presence of a Lewis acid
Cash, Daniel,Combs, Angela,Dragojlovic, Veljko
, p. 1143 - 1145 (2004)
Addition of a water-stable Lewis acid, indium trichloride, improved the rate of photochemical methoxycarbonylation of bromoalkanes. Primary and secondary bromoalkanes were carbonylated in good yields. Carbonylation of tertiary substrates was somewhat more difficult and some of them reacted too slowly for the reaction to be of a preparative value.
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.
Solid-state chlorodecarboxylation of mono- and dicarboxylic acids with the Pb(OAc)4-MCl system
Nikishin,Sokova,Chizhov,Makhaev,Kapustina
, p. 2200 - 2204 (2007/10/03)
Solid state reactions of acids RCOOH (R = n-C7H15, BuC(Et)H, n-C9H19, PhCH2, PhCH 2CH2, H2C=CH(CH2)8, or MeOOC(CH2)3) with Pb(OAc)4 combined with KCl, NaCl, CdCl2, or NH4Cl in the absence of a solvent and without mechanical activation afford chlorohydrocarbons RCl. The corresponding reactions of acids HOOC(CH2)nCOOH (n = 3-6) give dichloroalkanes Cl(CH2)nCl and γ-butyrolactone (n = 3).