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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 transformation of peroxides 541.
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C157: The transformation of peroxides 541.

Mentions: This difference is apparently attributable to the following two factors: (1) the lower nucleophilicity of the secondary hydroxy group compared to the tertiary hydroxy group; (2) the conformer, which would be suitably orientated towards the nucleophilic attack, is sterically unfavored in the case of R2 = H. At −20 °C, the transformation of 541d into a conformational isomer occurs more slowly than the thermal decomposition giving 543d (Scheme 157). Thermal rearrangements of strained cyclic peroxides 544a–d and 546a–e provide a versatile tool for the synthesis of carbonyl compounds 545a–d and 547a–e and heterocyclic systems 548 and 549 (Scheme 158) [498–499].


Rearrangements of organic peroxides and related processes
The transformation of peroxides 541.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C157: The transformation of peroxides 541.
Mentions: This difference is apparently attributable to the following two factors: (1) the lower nucleophilicity of the secondary hydroxy group compared to the tertiary hydroxy group; (2) the conformer, which would be suitably orientated towards the nucleophilic attack, is sterically unfavored in the case of R2 = H. At −20 °C, the transformation of 541d into a conformational isomer occurs more slowly than the thermal decomposition giving 543d (Scheme 157). Thermal rearrangements of strained cyclic peroxides 544a–d and 546a–e provide a versatile tool for the synthesis of carbonyl compounds 545a–d and 547a–e and heterocyclic systems 548 and 549 (Scheme 158) [498–499].

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