Trifuoroperacetic acid in consecutive Criegee rearrangement and carboxonium ions generation

Krasutsky, Pavel A.; Kolomitsyn, Igor V.

doi:10.3998/ark.5550190.0006.412

Cited by 3 publications

References 28 publications

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Criegee Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The rearrangement of peroxy ester into ketone, ester, or carbonate and alcohol via oxygen insertion or consecutive oxygen insertion is generally known as the Criegee rearrangement. The peroxy ester is primarily formed from the reaction between peracid and tertiary alcohol. The often‐used peracids include p ‐nitroperbenzoic acid and trifluoroperacetic acid because they are strong enough and give good leaving groups. It is also found that the migrating group rearranges from a position anti ‐periplanar to the dissociating oxygen‐oxygen bond of the peroxy ester and the electron‐donating ability of the migrating group facilitates such movement. It has been reported that this reaction occurs via an ionic mechanism. The major differences between the Criegee rearrangement and the Baeyer–Villiger oxidation have also been summarized.

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Criegee Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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Trifluoroperacetic Acid in Consecutive Criegee Rearrangement and Carboxonium Ions Generation

Krasutsky

Kolomitsyn

2005

ChemInform

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Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

182

136

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SummaryThis 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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Trifuoroperacetic acid in consecutive Criegee rearrangement and carboxonium ions generation

Cited by 3 publications

References 28 publications

Criegee Rearrangement

Criegee Rearrangement

Trifluoroperacetic Acid in Consecutive Criegee Rearrangement and Carboxonium Ions Generation

Rearrangements of organic peroxides and related processes

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