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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 oxidation of tertiary alcohols 200a–g, 203a,b, and 206.
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C59: The oxidation of tertiary alcohols 200a–g, 203a,b, and 206.

Mentions: The oxidation of tertiary alcohols 200a–g, 203a,b, and 206, involving the rearrangement of hydroperoxides 201a–g, 204a,b, and 207, occurs in good yields in the presence of such systems as NaBO3·4H2O/BF3·Et2O [328], H2O2/BF3·Et2O, and H2O2/p-TsOH [329] (Scheme 59). The Hock rearrangement can be used to prepare alcohols 202a–g, 205, and 208 containing electron-donating substituents.


Rearrangements of organic peroxides and related processes
The oxidation of tertiary alcohols 200a–g, 203a,b, and 206.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C59: The oxidation of tertiary alcohols 200a–g, 203a,b, and 206.
Mentions: The oxidation of tertiary alcohols 200a–g, 203a,b, and 206, involving the rearrangement of hydroperoxides 201a–g, 204a,b, and 207, occurs in good yields in the presence of such systems as NaBO3·4H2O/BF3·Et2O [328], H2O2/BF3·Et2O, and H2O2/p-TsOH [329] (Scheme 59). The Hock rearrangement can be used to prepare alcohols 202a–g, 205, and 208 containing electron-donating substituents.

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.