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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 rearrangements of bicyclic endoperoxides having electron-withdrawing substituents.
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C76: The base-catalyzed rearrangements of bicyclic endoperoxides having electron-withdrawing substituents.

Mentions: A further study [352] on the base-catalyzed rearrangements of substituted bicyclic endoperoxides showed that the pathway of the rearrangement is largely determined by the position of the substituent. The rearrangement of endoperoxides 247a,b containing an electron-withdrawing substituent in the seven-membered ring occurs mainly via a retro-aldol cleavage giving rise to formyl benzoates 248a,b (Scheme 76).


Rearrangements of organic peroxides and related processes
The base-catalyzed rearrangements of bicyclic endoperoxides having electron-withdrawing substituents.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C76: The base-catalyzed rearrangements of bicyclic endoperoxides having electron-withdrawing substituents.
Mentions: A further study [352] on the base-catalyzed rearrangements of substituted bicyclic endoperoxides showed that the pathway of the rearrangement is largely determined by the position of the substituent. The rearrangement of endoperoxides 247a,b containing an electron-withdrawing substituent in the seven-membered ring occurs mainly via a retro-aldol cleavage giving rise to formyl benzoates 248a,b (Scheme 76).

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.