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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.


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The multistep transformation of (R)-carvone (494) to endoperoxides 496a–e.
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C142: The multistep transformation of (R)-carvone (494) to endoperoxides 496a–e.

Mentions: A 1:1 mixture of the diastereomeric hydroperoxides 495a–e was synthesized by ozonolysis of (R)-carvone (494) and in situ trapping with primary alcohols ROH (R = Me, Et, Bu, Pent, Oct). Further cyclization of these hydroperoxides 495a–e using the sodium methanolate/MeOH system results in endoperoxides 496a–e exhibiting antimalarial activity (Scheme 142) [461].


Rearrangements of organic peroxides and related processes
The multistep transformation of (R)-carvone (494) to endoperoxides 496a–e.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C142: The multistep transformation of (R)-carvone (494) to endoperoxides 496a–e.
Mentions: A 1:1 mixture of the diastereomeric hydroperoxides 495a–e was synthesized by ozonolysis of (R)-carvone (494) and in situ trapping with primary alcohols ROH (R = Me, Et, Bu, Pent, Oct). Further cyclization of these hydroperoxides 495a–e using the sodium methanolate/MeOH system results in endoperoxides 496a–e exhibiting antimalarial activity (Scheme 142) [461].

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.


Related in: MedlinePlus