Copper (II) chloride / tetrabutylammonium bromide catalyzed oxidation of 2,6-diisopropylnaphthalene and 4,4′-diisopropylbiphenyl

Abstract

Abstract:The oxidation processes of 2,6-diisopropylnaphthalene and 4,4'-diisopropylbiphenyl with oxygen in the presence of a catalyst, composed of copper(II) chloride and tetrabutylammonium bromide, were investigated. It was found that, in essence, only one isopropyl group undergoes oxidation, and obtained mixtures contained mainly peroxide, alcohol, ketone and only small amounts of hydroperoxide. © Versita Sp. z o.o.

Aerobic Copper-Catalyzed Organic Reactions

“…41 Monoalcohol and peroxide dimers were the major products, along with smaller amounts of ketone, monohydroperoxide, and bishydroperoxide. Trace amounts of substrate underwent oxidation at both benzylic positions.…”

“…Orlinska and Zawadiak attempted the oxidation of more complex substrates, 4,4′-diisopropylbiphenyl and 2,6-diisopropylnaphthalene, using CuCl 2 and n -Bu 4 NBr under oxygen . Monoalcohol and peroxide dimers were the major products, along with smaller amounts of ketone, monohydroperoxide, and bishydroperoxide.…”

Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles

“…Moreover, molten TBAB was also employed as an efficient ionic liquid to carry out organic transformations under solvent-free conditions [ 23 , 24 , 25 ]. In some reactions, it was observed that the addition of a catalytic amount of TBAB as co-catalyst enhanced the reaction rate as well as product yields [ 26 , 27 , 28 , 29 , 30 ]. The abovementioned unique capabilities of TBAB make this catalyst very attractive.…”