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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 Kornblum–DeLaMare rearrangement of peroxides 242a,b.
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C75: The Kornblum–DeLaMare rearrangement of peroxides 242a,b.

Mentions: The reaction of endoperoxide 242a containing an electron-donating substituent at the double bond with bases results in the rearrangement product diketone 243. Under the same conditions, the base-catalyzed rearrangement of endoperoxide 242b containing an electron-withdrawing substituent leads to a product mixture of hydroxy ketone 244, and diketones 245 and 246 (Scheme 75) [353].


Rearrangements of organic peroxides and related processes
The Kornblum–DeLaMare rearrangement of peroxides 242a,b.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C75: The Kornblum–DeLaMare rearrangement of peroxides 242a,b.
Mentions: The reaction of endoperoxide 242a containing an electron-donating substituent at the double bond with bases results in the rearrangement product diketone 243. Under the same conditions, the base-catalyzed rearrangement of endoperoxide 242b containing an electron-withdrawing substituent leads to a product mixture of hydroxy ketone 244, and diketones 245 and 246 (Scheme 75) [353].

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.