1014-60-4Relevant articles and documents
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Olah,G.A.,Mo,Y.K.
, p. 3221 - 3223 (1973)
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Barclay,Betts
, (1955)
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Interconversion equilibria between tert-butylbenzenes and tert-butyltoluenes
Nesterov,Nesterova,Vodenkova,Naumkin,Repkin
, p. 193 - 200 (2008)
The equilibrium of six positional isomerization reactions in the systems of sterically unhindered tert-butylbenzenes (TBB) and tert-butyltoluenes (TBT) was experimentally studied in the liquid phase over a wide temperature range. The thermodynamic charact
Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4-Dioxane
Hokamp, Tobias,Dewanji, Abhishek,Lübbesmeyer, Maximilian,Mück-Lichtenfeld, Christian,Würthwein, Ernst-Ulrich,Studer, Armido
supporting information, p. 13275 - 13278 (2017/10/09)
A practical method for radical chain reduction of various aryl bromides and chlorides is introduced. The thermal process uses NaH and 1,4-dioxane as reagents and 1,10-phenanthroline as an initiator. Hydrodehalogenation can be combined with typical cyclization reactions, proving the nature of the radical mechanism. These chain reactions proceed by electron catalysis. DFT calculations and mechanistic studies support the suggested mechanism.
Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes
Knorr, Rudolf,Rossmann, Eva C.,Knittl, Monika,B?hrer, Petra
supporting information, p. 5332 - 5338 (2014/12/10)
Hydrophobically shielded alkynes HCC-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2CC(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DCC-aryl furnished initially only the E stereoisomer of DHCC(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-CC-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3produced H2CC(-SnMe3)-aryl with well resolved long range 119Sn NMR coupling constants.