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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 Kornblum–DeLaMare rearrangement of epoxy dioxanes 290a–d.
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C86: The Kornblum–DeLaMare rearrangement of epoxy dioxanes 290a–d.

Mentions: The reaction of unsymmetrical epoxy dioxanes 290a–d with triethylamine is accompanied by the 1,2-dioxane-ring opening to form 4-hydroxy-2,3-epoxy ketones 291a–d in high yields. The base catalysis involves the abstraction of the most acidic α-proton in the vicinity of the O–O bond followed by the rearrangement accompanied by the O–O-bond cleavage to form 4-hydroxy-2,3-epoxy ketones (Scheme 86) [364].


Rearrangements of organic peroxides and related processes
The Kornblum–DeLaMare rearrangement of epoxy dioxanes 290a–d.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C86: The Kornblum–DeLaMare rearrangement of epoxy dioxanes 290a–d.
Mentions: The reaction of unsymmetrical epoxy dioxanes 290a–d with triethylamine is accompanied by the 1,2-dioxane-ring opening to form 4-hydroxy-2,3-epoxy ketones 291a–d in high yields. The base catalysis involves the abstraction of the most acidic α-proton in the vicinity of the O–O bond followed by the rearrangement accompanied by the O–O-bond cleavage to form 4-hydroxy-2,3-epoxy ketones (Scheme 86) [364].

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.