Novel tert-Butyl Migration in Copper-Mediated Phenol Ortho-Oxygenation Implicates a Mechanism Involving Conversion of a 6-Hydroperoxy-2,4-cyclohexadienone Directly to an o-Quinone
Copper mediated ortho-oxygenation of phenolates may proceed through the generation of a 6-peroxy-2,4-cyclohexadienone intermediate. To test this theory, we studied the fate of sodium 4-carbethoxy-2,6-di-tert-butylphenolate, where the ortho-oxygenation sit
Mandal, Subrata,Macikenas, Dainius,Protasiewicz, John D.,Sayre, Lawrence M.
p. 4804 - 4809
(2007/10/03)
Electrochemical Oxidation, VII. Synthesis and Structure of 7-tert-Butyl-2-methylbenzoxazoles
Anodic oxidation of 15 tert-butylphenols 1a - o in absolute acetonitrile or acetonitrile/perchloric acid leads to the corresponding 7-tert-butyl-2-methylbenzoxazoles 3a - o.The proof of the structure was achieved by independent synthesis of 3k, and by 13C NMR spectroscopy as well as by X-ray analysis of 7-tert-butyl-2-methyl-5-benzoxazolecarbaldehyde (3j).The influence of the supporting electrolyte on the formation of the oxidation products is discussed.
Dreher, Eberhard-Ludwig,Bracht, Juergen,El-Mobayed, Medhat,Huetter, Peter,Winter, Werner,Rieker, Anton
p. 288 - 308
(2007/10/02)
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