gem-Bishydroperoxides

Abstract

This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research spotlight gem-Bishydroperoxides Compiled by Johannes H. van Tonder Johannes grew up in the diamond city Kimberley, South Africa. He pursued his interest in science by obtaining a B.Sc. degree in chemistry and biology in 2004 from the University of the Free State. His fondness for organic chemistry led him to procure a M.Sc. degree from the same institution in 2008. He is currently completing a Ph.D. degree under the supervision of Professor B. C. B. Bezuidenhoudt at the University of the Free State.

Di(hydroperoxy)cycloalkanes Stabilized via Hydrogen Bonding by Phosphine Oxides: Safe and Efficient Baeyer–Villiger Oxidants

“…The unoptimized isolated yields were high, with 76% for 1 and 88% for 3 . For the synthesis of adduct 2 , the hydrogen peroxide in (Cy 3 PO·H 2 O 2 ) 2 , is replaced by the preformed di­(hydroperoxy)­cyclohexane. , Adduct 4 is obtained in 84% yield after the synthesis of 2 from (Cy 3 PO·H 2 O 2 ) 2 , and cyclohexanone and exposing the biphasic reaction mixture to the atmosphere for several days. Alternatively, 4 can be generated quantitatively by thermal decomposition of 2 in chlorobenzene at 110 °C within several hours.…”

“…For the past decade, di­(hydroperoxy)­cycloalkanes were intensively studied, and practically rediscovered as inexpensive starting reagents with multifaceted potential for applications in academia and industry. For example, they have been shown to play important roles in Baeyer–Villiger oxidations. − Correspondingly, easy and straightforward syntheses for di­(hydroperoxy)­cycloalkanes have been described. , …”

“…The research presented in this Article aims to explore new adducts of peroxides, stabilized by hydrogen bonding to phosphine oxides, as oxidizing agents with highly desirable characteristics. The work is based on the recent discovery that H 2 O 2 and di­(hydroperoxy)­alkanes, (HOO) 2 CRR′, , are stabilized by well-defined hydrogen bonding to phosphine oxides without compromising their oxidative efficiency. − In earlier work, our research on immobilized catalysts with phosphine linkers − necessitated the investigation of phosphine oxides adsorbed on silica surfaces and their dynamic properties . For these studies, very clean phosphine oxides were essential, and were best obtained by oxidizing phosphines with aqueous H 2 O 2 in a biphasic system .…”

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

“…Silicon‐containing and organic peroxides are important too, but they can be difficult to synthesize and remove after the reactions . Recently, bishydroperoxides have also received some attention …”

Hydrogen Peroxide and Di(hydroperoxy)propane Adducts of Phosphine Oxides as Stoichiometric and Soluble Oxidizing Agents

“…[22] Recently,b ishydroperoxides have also received some attention. [23,24] The ideal oxidizing agent is an easy to synthesize peroxide of reproducible stoichiometry that is soluble in organic solvents.I ts hould be mechanicallya nd thermally stablea ta mbient temperature over prolongedt ime periods, while retaining its oxidizing power.A dditionally,asolid oxidizing agent would be preferred duet ot he ease of handling and application. We recently reported on an ew class of materials, hydrogen peroxide adducts of phosphine oxides, for example, (Cy 3 PO·H 2 O 2 ) 2 .…”