Sulfuric Acid

Krow, Grant R.

doi:10.1002/047084289x.rs136

Cited by 1 publication

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References 37 publications

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“…Our goal was to develop a convenient and selective single-step access to β-hydroperoxy-β-peroxylactones 6 via BF 3 -catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters 1 and their silyl enol ethers 2 , alkyl enol ethers 3 , enol acetates 4 , cyclic acetals 5 , with H 2 O 2 (Scheme ). We have concentrated on the use of boron trifluoride as the peroxidation catalyst because this catalyst was shown to work well in a previous synthesis of bishydroperoxides, 1,1′-bishydroperoxydi(cycloalkyl) peroxides, and 1,2,4-trioxanes , as well as various peroxides from acetals and enol ethers …”

Section: Resultsmentioning

confidence: 99%

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF₃-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

et al. 2018

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We have discovered synthetic access to βhydroperoxy-β-peroxylactones via BF 3 -catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals, with H 2 O 2 . Strikingly, independent of the choice of starting material, these reactions converge at the same β-hydroperoxyβ-peroxylactone products, i.e., the peroxy analogues of the previously elusive cyclic Criegee intermediate of the Baeyer− Villiger reaction. Computed thermodynamic parameters for the formation of the β-hydroperoxy-β-peroxylactones from silyl enol ethers, enol acetates, and cyclic acetals confirm that the β-peroxylactones indeed correspond to a deep energy minimum that connects a variety of the interconverting oxygen-rich species at this combined potential energy surface. The target β-hydroperoxy-β-peroxylactones were synthesized from β-ketoesters, and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals were obtained in 30−96% yields. These reactions proceed under mild conditions and open synthetic access to a broad selection of β-hydroperoxy-βperoxylactones that are formed selectively even in those cases when alternative oxidation pathways can be expected. These βperoxylactones are stable and can be useful for further synthetic transformations.

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Section: Resultsmentioning

confidence: 99%

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF₃-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

et al. 2018

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show abstract

Sulfuric Acid

Cited by 1 publication

References 37 publications

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF₃-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF₃-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

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Sulfuric Acid

Cited by 1 publication

References 37 publications

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

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Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF₃-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF₃-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones