Baeyer‐Villiger Oxidation

doi:10.1002/9780470638859.conrr036

Comprehensive Organic Name Reactions and Reagents 2010

DOI: 10.1002/9780470638859.conrr036

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Baeyer‐Villiger Oxidation

Abstract: Oxidation of ketones or cyclic ketones into esters or lactones by peracids or hydrogen peroxide is known as the Baeyer–Villiger oxidation. Some of the typical peracids have been found to involve in this type of the reaction are peroxybenzoic acid, m ‐chloroperoxybenzoic acid ( m CPBA), peroxyacetic acid, and trifluoroperoxyacetic acid. In this reaction the substituted group often migrates in the following order: tertiary > secondary > cyclohexyl > benzyl… Show more

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Cited by 3 publications

References 143 publications

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Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzo[b][1,4]oxazin‐3(4H)‐ones

Saleh,

Mondal,

Senapati

et al. 2023

Asian J Org Chem

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A sequential one‐pot direct strategy for the synthesis of 2‐hydroxy‐2‐substituted‐2H‐benzo[b][1,4]oxazin‐3(4H)‐ones is developed under ambient conditions with moderate to good yields (up to 75 %) by regioselective ring‐opening of spiro‐epoxy/aziridine oxindoles with 50 % aq. H2O2 followed by rearrangement reaction in presence of amberlyst‐15 catalyst. Further, sequential reaction with aldehydes/ketones and carbonyldiimidazole (CDI) gave spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolan]‐3(4H)‐ones and spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolane]‐2′,3(4H)‐diones, respectively.

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Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzo[b][1,4]oxazin‐3(4H)‐ones

Saleh,

Mondal,

Senapati

et al. 2023

Asian J Org Chem

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Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives

2021

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For the first time, the sequential reaction of peroxyoxindole that involves base-promoted oxidative fragmentation to isocyanate formation and primary amine or amino alcohol accelerated skeletal rearrangement to synthesize exo-olefinic-substituted quinazolinone or oxazoloquinazolinone is reported. The advantages of this new reaction include a broad substrate scope and transition-metal-free and room-temperature conditions. The formation of the isocyanate as a key intermediate that accelerates oxidative skeletal rearrangement has been confirmed by trapping experiments and spectroscopic evidence.

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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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Baeyer‐Villiger Oxidation

Cited by 3 publications

References 143 publications

Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzo[b][1,4]oxazin‐3(4H)‐ones

Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzo[b][1,4]oxazin‐3(4H)‐ones

Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives

Rearrangements of organic peroxides and related processes

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