Angewandte Chemie - International Edition

, volume 57 , issue 13 , pages 3372-3376

Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate.

Vera A. Vil’ ^{1, 2, 3}

Gabriel Dos Passos Gomes ⁴

Oleg V Bityukov ^{1, 3}

Konstantin A. Lyssenko ⁵

Gennady I. Nikishin ¹

Igor V. Alabugin ⁴

Alexander O. Terent'ev ^{1, 2, 3}

Hide authors affiliations Show authors affiliations: 5 affiliations

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky Prosp. 119991 Moscow Russian Federation |

D. I. Mendeleev University of Chemical Technology of Russia Moscow Russian Federation |

All-Russian Research Institute for Phytopathology Moscow Region Russian Federation |

⁴

Department of Chemistry and Biochemistry Florida State University Tallahassee FL USA |

⁵

A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences 119991 Moscow Russian Federation |

Publication type: Journal Article

Publication date: 2018-02-23

Wiley

Angewandte Chemie - International Edition

scimago Q1

wos Q1

SJR: 5.550

CiteScore: 27.6

Impact factor: 16.9

ISSN: 14337851, 15213773

DOI: 10.1002/anie.201712651

Copy DOI

PubMed ID: 29385307

General Chemistry

Catalysis

Abstract

The instability of hydroxy peroxyesters, the elusive Criegee intermediates of the Baeyer-Villiger rearrangement, can be alleviated by selective deactivation of the stereoelectronic effects that promote the 1,2-alkyl shift. Stable cyclic Criegee intermediates constrained within a five-membered ring can be prepared by mild reduction of the respective hydroperoxy peroxyesters (β-hydroperoxy-β-peroxylactones) which were formed in high yields in reaction of β-ketoesters with BF3 ⋅Et2 O/H2 O2 .

Found

14 citations

Vil' Vera

PhD in Chemistry

86 publications, 1 959 citations, 3 reviews

h-index: 24

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

10 citations

Yaremenko Ivan

PhD in Chemistry

59 publications, 1 559 citations, 5 reviews

h-index: 24

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

8 citations

Radulov Peter

PhD in Chemistry

37 publications, 530 citations, 22 reviews

h-index: 13

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

7 citations

Barsegyan Yana

🥼 🤝

PhD in Chemistry

16 publications, 171 citations

h-index: 7

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

6 citations

Medvedev Michael

PhD in Physics and Mathematics, associate professor

85 publications, 2 051 citations, 7 reviews

h-index: 19

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

2 citations

Medvedev Alexander

PhD in Chemistry

81 publications, 2 173 citations

h-index: 24

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

1 citation

Osipov Sergey

DSc in Chemistry

138 publications, 2 725 citations, 3 reviews

h-index: 29

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Karasik Andrey

DSc in Chemistry, professor, associate member of the Russian Academy of Sciences

224 publications, 2 591 citations

h-index: 26

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Luminescence

Phosphorus ligands

1 citation

Lyssenko Konstantin

🥼 🤝

DSc in Chemistry, professor

898 publications, 15 140 citations, 2 reviews

h-index: 50

Lomonosov Moscow State University

National Research University Higher School of Economics

Research interests

Supramolecular chemistry

1 citation

Dotsenko Viktor

DSc in Chemistry, professor

244 publications, 2 706 citations, 2 reviews

h-index: 22

North Caucasus Federal University

Kuban State University

Research interests

Active methylene compounds

Biological activity

Heterocyclic compounds

Malononitrile

Selenoamides

Thioamides

1 citation

Zagidullin Almaz

🥼 🤝

PhD in Chemistry

81 publications, 876 citations

h-index: 17

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials

Coordination chemistry of phosphorus

Organoelement chemistry

Organophosphorus chemistry

Synthesis of chiral phosphorus-containing ligands

1 citation

Aksenov Aleksandr

🥼 🤝

DSc in Chemistry, professor

243 publications, 2 163 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 707 citations

h-index: 30

Ural Federal University

1 citation

Budekhin Roman

🤝

6 publications, 23 citations

h-index: 3

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

1 citation

Ilkin Vladimir

PhD in Chemistry

16 publications, 179 citations

h-index: 7

Ural Federal University

Research interests

Catalysis

Heterocyclic compounds

Organic Chemistry

Synthetic Organic Chemistry

1 citation

Krylov Igor

PhD in Chemistry

78 publications, 1 876 citations, 18 reviews

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Green chemistry

Organic Chemistry

Organic electrochemistry

Organic synthesis

Photochemistry

Plant protection

1 citation

Prolomov Ilya

🤝

2 publications, 4 citations

h-index: 2

Mendeleev University of Chemical Technology of Russia

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Aminov Rishat

33 publications, 164 citations

h-index: 7

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

1 citation

Tikhomirov Alexander

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DSc in Chemistry, associate professor

59 publications, 910 citations

h-index: 17

Mendeleev University of Chemical Technology of Russia

Gause Institute of New Antibiotics

Research interests

Medicinal Chemistry

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GOST Copy

Vil’ V. A. et al. Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate. // Angewandte Chemie - International Edition. 2018. Vol. 57. No. 13. pp. 3372-3376.

GOST all authors (up to 50) Copy

Vil’ V. A., Gomes G. D. P., Bityukov O. V., Lyssenko K. A., Nikishin G. I., Alabugin I. V., Terent'ev A. O. Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate. // Angewandte Chemie - International Edition. 2018. Vol. 57. No. 13. pp. 3372-3376.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1002/anie.201712651

UR - https://doi.org/10.1002/anie.201712651

TI - Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate.

T2 - Angewandte Chemie - International Edition

AU - Vil’, Vera A.

AU - Gomes, Gabriel Dos Passos

AU - Bityukov, Oleg V

AU - Lyssenko, Konstantin A.

AU - Nikishin, Gennady I.

AU - Alabugin, Igor V.

AU - Terent'ev, Alexander O.

PY - 2018

DA - 2018/02/23

PB - Wiley

SP - 3372-3376

IS - 13

VL - 57

PMID - 29385307

SN - 1433-7851

SN - 1521-3773

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2018_Vil’,

author = {Vera A. Vil’ and Gabriel Dos Passos Gomes and Oleg V Bityukov and Konstantin A. Lyssenko and Gennady I. Nikishin and Igor V. Alabugin and Alexander O. Terent'ev},

title = {Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate.},

journal = {Angewandte Chemie - International Edition},

year = {2018},

volume = {57},

publisher = {Wiley},

month = {feb},

url = {https://doi.org/10.1002/anie.201712651},

number = {13},

pages = {3372--3376},

doi = {10.1002/anie.201712651}

}

MLA

Cite this

MLA Copy

Vil’, Vera A., et al. “Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate..” Angewandte Chemie - International Edition, vol. 57, no. 13, Feb. 2018, pp. 3372-3376. https://doi.org/10.1002/anie.201712651.

Publisher

Wiley

Journal

Angewandte Chemie - International Edition

scimago Q1

wos Q1

SJR

5.550

CiteScore

27.6

Impact factor

16.9

ISSN

14337851 (Print)

15213773 (Electronic)

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