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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 peroxidation of tertiary alcohols in the presence of a catalytic amount of acid.
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C56: The peroxidation of tertiary alcohols in the presence of a catalytic amount of acid.

Mentions: An attempt was made [324] to synthesize hydroperoxides through the peroxidation of tertiary alcohols in the presence of a catalytic amount of acid. The treatment of 185 with H2O2 in the presence of a catalytic amount of H2SO4 for 72 hours did not lead to the formation of products via the Hock rearrangement of hydroperoxides, bicyclic hydroperoxides and о-hydroxyphenyl alkyl ketones. Instead, cyclic 2-methylchroman-2-yl hydroperoxide 188, geminal bishydroperoxides 190, and condensation products of peroxides such as 191 were isolated (Scheme 56).


Rearrangements of organic peroxides and related processes
The peroxidation of tertiary alcohols in the presence of a catalytic amount of acid.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C56: The peroxidation of tertiary alcohols in the presence of a catalytic amount of acid.
Mentions: An attempt was made [324] to synthesize hydroperoxides through the peroxidation of tertiary alcohols in the presence of a catalytic amount of acid. The treatment of 185 with H2O2 in the presence of a catalytic amount of H2SO4 for 72 hours did not lead to the formation of products via the Hock rearrangement of hydroperoxides, bicyclic hydroperoxides and о-hydroxyphenyl alkyl ketones. Instead, cyclic 2-methylchroman-2-yl hydroperoxide 188, geminal bishydroperoxides 190, and condensation products of peroxides such as 191 were isolated (Scheme 56).

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.