Synthesis of unstrained Criegee intermediates: inverse α-effect and other protective stereoelectronic forces can stop Baeyer–Villiger rearrangement of γ-hydroperoxy-γ-peroxylactones-Reference-Cited by-同舟云学术

Synthesis of unstrained Criegee intermediates: inverse α-effect and other protective stereoelectronic forces can stop Baeyer–Villiger rearrangement of γ-hydroperoxy-γ-peroxylactones

Published:2020 Issue:20 Volume:11 Page:5313-5322
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Vil' Vera A.¹²³^ORCID,Barsegyan Yana A.¹²³,Kuhn Leah⁴⁵⁶⁷,Ekimova Maria V.¹²³⁸⁹,Semenov Egor A.¹²³⁸⁹,Korlyukov Alexander A.¹⁰²³¹¹²^ORCID,Terent'ev Alexander O.¹²³^ORCID,Alabugin Igor V.⁴⁵⁶⁷^ORCID

Affiliation:

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

2. Moscow

3. Russian Federation

4. Department of Chemistry and Biochemistry

5. Florida State University

6. Tallahassee

7. USA

8. D. I. Mendeleev University of Chemical Technology of Russia

9. Moscow 125047

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

11. Pirogov Russian National Research Medical University

Abstract

Protecting stereoelectronic effects prevent Baeyer–Villiger rearrangement and stabilize γ-OX-γ-peroxylactones (X = H, OH), the previously elusive non-strained Criegee intermediates.

Funder

Russian Science Foundation

National Science Foundation

Ministry of Science and Higher Education of the Russian Federation

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/SC/D0SC01025A

Reference89 articles.

1. Einwirkung des Caro'schen Reagens auf Ketone