Oxidation Reactions of 2,4,6-Tri-t-butylaniline

Abstract

Oxidation reactions of 2,4,6-tri-t-butylaniline with lead tetraacetate (LTA), lead tetrabenzoate (LTB), peroxybenzoic acid (PBA) and benzoyl peroxide (BPO) were studied and mechanisms of these reactions were briefly discussed. In the reaction with LTA, 4-acetoxy-1-imino-2,4,6-tri-t-butyl-2,5-cyclohexadiene (I), 2-acetamido-3,5-di-t-butylphenol (II) and 2-acetylimino-3,5-di-t-butyl-3,5-cyclohexadienone(III) were produced. Oxidation with LTB gave 4-benzoyloxy-1-imino-2,4,6-tri-t-butyl-2,5-cyclohexadiene (VI, major product) and 2-benzamido-3,5-di-t-butylphenol (VII). The reaction products with PBA were 2,4,6-tri-t-butylnitrosobenzene (VIII) and VII. In addition to the last two compounds, VI and 2,2′,4,4′,6,6′-hexa-t-butylazobenzene (XI) were obtained in the case of BPO.

Substrate Redox Non-innocence Inducing Stepwise Oxidative Addition Reaction: Nitrosoarene C–N Bond Cleavage on Low-Coordinate Cobalt(0) Species

“…31 In this regard, we report herein the first observation of a nitrosoarene C−N bond oxidative addition reaction between a three-coordinate cobalt(0) complex, [(IPr)Co(vtms) 2 ] (IPr = 1,3-bis(2′,6′diisopropylphenyl)imidazol-2-ylidene; vtms = vinyltrimethylsilane), and 2,4,6-tri(tert-butyl)-1-nitroso-benzene (Ar*NO). The reaction produces the first three-coordinate cobalt nitrosyl complex [ 32 with the nitrosoarene 2,4,6-tri(tert-butyl)-1-nitrosobenzene (Ar*NO, 2 equiv) 33 in toluene at 80 °C gave a green solution. After workup and recrystallization, green crystals of a cobalt nitrosyl aryl complex, [(IPr)Co(Ar*)(NO)] (1), were isolated in 46% yield (Scheme 1).…”

“…Treatment of [(IPr)­Co­(vtms) 2 ] with the nitroso­arene 2,4,6-tri­( tert -butyl)-1-nitroso­benzene (Ar*NO, 2 equiv) in toluene at 80 °C gave a green solution. After workup and recrystallization, green crystals of a cobalt nitrosyl aryl complex, [(IPr)­Co­(Ar*)­(NO)] ( 1 ), were isolated in 46% yield (Scheme ).…”

Blue Variable Stars from the MACHO Database. I. Photometry and Spectroscopy of the Large Magellanic Cloud Sample

“…Other models such as the "one-armed" density wave model (Okazaki 1997) seek to explain spectral line variations observed in Be stars.…”

Homolytic Scission of Interunitary Bonds in Lignin Induced by Ultrasonic Irradiation of MWL Dissolved in Dimethylsulfoxide

“…The spin trap reagent, 2,4,6-tri-tert-butylnitrosobenzene (BNB) was synthesized according to the method described in the literature and used after purification (Okazaki et al 1969).…”