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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.


The hydroxylation of cyclohexene (447) in the presence of tungstic acid.
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C128: The hydroxylation of cyclohexene (447) in the presence of tungstic acid.

Mentions: In a study on the hydroxylation of compounds containing a double bond to the corresponding α-glycols, the tungstic acid-catalyzed reaction of cyclohexene (447) with 90% hydrogen peroxide in methanol, ethanol, or isopropanol afforded the corresponding 2-alkoxycyclohexanols 448a–c in 70, 41, and 21% yields, respectively, as well as the trans-1,2-cyclohexanediols 449a–d (Scheme 128) [447].


Rearrangements of organic peroxides and related processes
The hydroxylation of cyclohexene (447) in the presence of tungstic acid.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C128: The hydroxylation of cyclohexene (447) in the presence of tungstic acid.
Mentions: In a study on the hydroxylation of compounds containing a double bond to the corresponding α-glycols, the tungstic acid-catalyzed reaction of cyclohexene (447) with 90% hydrogen peroxide in methanol, ethanol, or isopropanol afforded the corresponding 2-alkoxycyclohexanols 448a–c in 70, 41, and 21% yields, respectively, as well as the trans-1,2-cyclohexanediols 449a–d (Scheme 128) [447].

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.