Oxidants oxone

The epoxidation of olefins catalyzed by iminium salts and amines (or ammonium salts) is emerging as a new technique for the functionalization of simple aUcenes. These catalysts have relatively simple structures and hence are easily produced at scale they offer potential as green oxidation catalysts. These organic salts are effective oxygen transfer reagents towards electron-rich unfunctionalized olefins. For the iminium salt systems oxone oxidizes an iminium salt to the oxaziridi-nium intermediate, which then transfers oxygen to the olefin and as oxone reacts readily with iminium ions to regenerate the oxaziridinium species catalyti-cally, efficient oxidation is possible. 

Curini, M. Rosati, O. Pisani, E. Preparation of diphenylmethyl esters by oxone oxidation of benzophenone hydrazone. Tetrahedron Lett. 1997, 38, 1239-1240. 

Simple amines in the presence of Oxone oxidize alkenes to oxiranes. For example, Oxone, pyridine, and a 2-pyrrolidine derivative in a medium of aqueous acetonitrile selectively converts the triene in Equation (72) to a single epoxide. This process also proceeds using noncyclic alkenes. The mechanism is believed to proceed via a single-electron transfer (SET) process involving radical cation intermediates <2000JA8317>. 

Oxone oxidizes iminium salts to an oxazitidinium intermediate 179, which can transfer oxygen to an alkene to form an epoxide and regenerate the iminium salt. ... 

B.M. Trost, R. Braslau, Tetra-n-butylammonium oxone. Oxidations under anhydrous conditions, J. Org. Chem. 53 (1988) 532. 

A Wittig reaction of the THF-swollen polystyrene resin (48) with the P-ketomethylene ylide (49) has been used to functionalise the resin for further transformations. " The aza-Wittig reaction of N-Boc-triphenyliminophosphorane (50) with 4-cyanobenzaldehyde followed by oxone oxidation provides the stable oxaziridine (51) (Scheme 4) which acts as an electrophilic aminating agent towards amines and enolates. ... 

Oxone oxidizes metal complexes including tris[(2-oxazolinyl)-phenolato] manganese(III) which, in conjunction with -Bu4NBr, is an effective oxidant for aromatic and primary and secondary aliphatic alcohols. ... 

Oxone, which is commercially available as a 2 1 1 mixture of KHSO5, KHSO4, and K2SO4, has been used for the oxidation of sulfides to sulfoxides [15]. It shows a tendency to overoxidation, and was originally used for the oxidation of sulfides to sulfones [16]. More recently, some improvements were obtained with surface-mediated oxone oxidations, the oxone being bound to a silica gel surface (Eq. (8.3)). However, some sulfone was still formed. 

The synthetic route of sulfite-linked cycloaliphatic epoxy resin is presented in Figure 8.13 [38]. The synthesis of intermediate is achieved via the nucleophilic substitution reaction of thionyl chloride with cyclohex-3-enyl-1-methanol. Subsequently, Epo-S is obtained by epoxidation with OXONE oxidant. Epo-S is liquid at room temperature which is favorable for the underfilling encapsulation for high-density electronic packaging technologies such as flip chip plastic ball grid array (FC-PBGA) and MCM. 

The six-membered iodine heterocycles 233 have been synthesized by the Oxone oxidation of the corresponding 2-iodophenylacetic acids 232 in water (Scheme 51). Interestingly, the X-ray structural study demonstrated that the products 233 exist in the solid state in the open tautomeric form of the pseudocychc acids 234 (2010JOC8416). 

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