76905-73-2Relevant articles and documents
Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis
Yu, Peng,Bismuto, Alessandro,Morandi, Bill
supporting information, p. 2904 - 2910 (2020/01/25)
Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXII. THERMAL TRANSFORMATIONS OF EXO-CHLORINE-SUBSTITUTED TOLUENES
Voronkov, M. G.,Deryagina, E. N.,Shagun, L. G.,Vitkovskii, V. Yu.
, p. 962 - 966 (2007/10/02)
The gas-phase pyrolysis of exo-chlorine-substituted toluenes in an atmosphere of nitrogen or hydrogen sulfide was investigated.Hydrogen sulfide stimulates the thermolysis of benzyl chloride, accelerating the formation of toluene and stilbene at 430 deg C.The other reaction products are anthracene and bibenzyl.Similar compounds and also phenanthrene are formed during the pyrolysis of benzylidene chloride in an atmosphere of nitrogen or hydrogen sulfide (500 deg C).Benzotrichloride is distinguished by its high stability; its pyrolysis mainly with the formation of 1,2-dichloro-1,2-diphenylethylene is realized at temperatures above 550 deg C.With hydrogen sulfide it reacts at 400 deg C to form bibenzyl, stilbene, anthracene, phenanthrene, and thianaphtenothianaphthene.The latter is the main product in a recirculation-type system.