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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.

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The base-catalyzed rearrangement of cyclic peroxides 488a–g.
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C140: The base-catalyzed rearrangement of cyclic peroxides 488a–g.

Mentions: The base-catalyzed rearrangement of cyclic peroxides 488a–g, which are prepared by the manganese-catalyzed oxidation of 1- and 1,2-disubstituted cyclopropanols 487a–g, provides a convenient approach to the synthesis of aliphatic and arylaliphatic α,β-epoxy ketones 489a–g. The latter compounds are attractive substrates for the synthesis of for example natural compounds (Scheme 140) [459].


Rearrangements of organic peroxides and related processes
The base-catalyzed rearrangement of cyclic peroxides 488a–g.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C140: The base-catalyzed rearrangement of cyclic peroxides 488a–g.
Mentions: The base-catalyzed rearrangement of cyclic peroxides 488a–g, which are prepared by the manganese-catalyzed oxidation of 1- and 1,2-disubstituted cyclopropanols 487a–g, provides a convenient approach to the synthesis of aliphatic and arylaliphatic α,β-epoxy ketones 489a–g. The latter compounds are attractive substrates for the synthesis of for example natural compounds (Scheme 140) [459].

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.