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

Interrupted Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate Full article

Journal

Angewandte Chemie International Edition
ISSN: 1433-7851 , E-ISSN: 1521-3773

Output data

Year: 2018, Volume: 57, Number: 13, Pages: 3372-3376 Pages count : 5 DOI: 10.1002/anie.201712651

Authors

Vil Vera A. ^1,3,4 , Gomes Gabriel dos Passos ² , Bityukov Oleg V. ^1,4 , Lyssenko Konstantin A. ⁵ , Nikishin Gennady I. ¹ , Alabugin Igor V. ² , Terent'ev Alexander O. ^1,3,4

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky prosp. 119991 Moscow Russian Federation
2	Department of Chemistry and Biochemistry Florida State University Tallahassee FL USA
3	D. I. Mendeleev University of Chemical Technology of Russia Moscow Russian Federation
4	All-Russian Research Institute for Phytopathology Moscow Region Russian Federation
5	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Moscow, Russian Federation.

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⋅Et2O/H2O2.

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. V.57. N13. P.3372-3376. DOI: 10.1002/anie.201712651 WOS Scopus OpenAlex

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