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Rearrangements of organic peroxides and related processes

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ABSTRACT

This review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes are also analyzed. The rearrangements and related processes of important natural and synthetic peroxides are discussed separately.

No MeSH data available.


General mechanism of the Lewis acid-catalyzed Baeyer–Villiger rearrangement.
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C3: General mechanism of the Lewis acid-catalyzed Baeyer–Villiger rearrangement.

Mentions: The present review covers a more modern aspect of this reaction, viz., the performance of the process using hydrogen peroxide. Oxidizing systems containing hydrogen peroxide as the oxidizing agent allow the usual and asymmetric oxidation of the substrate to the target product with high conversion and yield. In recent years, the inexpensive, commercially available, and environmentally friendly H2O2 was utilized in the Baeyer–Villiger reaction with increasing frequency. Various catalysts that activate hydrogen peroxide, such as heterogeneous catalysts based on solid acids [201], zeolites [202–203], Se [204], As [205], Co [206], sulfonated organic ion exchange resins [203,207], and homogeneous catalysts based on Pt [208], Zr [209], Re [210–211], Se [212–213], As [205], Mo [214], Co [215], Brønsted [216], and Lewis acids [217] are described in the literature. The general mechanism of a Lewis acid-catalyzed Baeyer–Villiger rearrangement is presented in Scheme 3 [200,218].


Rearrangements of organic peroxides and related processes
General mechanism of the Lewis acid-catalyzed Baeyer–Villiger rearrangement.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979652&req=5

C3: General mechanism of the Lewis acid-catalyzed Baeyer–Villiger rearrangement.
Mentions: The present review covers a more modern aspect of this reaction, viz., the performance of the process using hydrogen peroxide. Oxidizing systems containing hydrogen peroxide as the oxidizing agent allow the usual and asymmetric oxidation of the substrate to the target product with high conversion and yield. In recent years, the inexpensive, commercially available, and environmentally friendly H2O2 was utilized in the Baeyer–Villiger reaction with increasing frequency. Various catalysts that activate hydrogen peroxide, such as heterogeneous catalysts based on solid acids [201], zeolites [202–203], Se [204], As [205], Co [206], sulfonated organic ion exchange resins [203,207], and homogeneous catalysts based on Pt [208], Zr [209], Re [210–211], Se [212–213], As [205], Mo [214], Co [215], Brønsted [216], and Lewis acids [217] are described in the literature. The general mechanism of a Lewis acid-catalyzed Baeyer–Villiger rearrangement is presented in Scheme 3 [200,218].

View Article: PubMed Central - HTML - PubMed

ABSTRACT

This review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes are also analyzed. The rearrangements and related processes of important natural and synthetic peroxides are discussed separately.

No MeSH data available.