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Literature DB >> 25337903

Ring-opening 1,3-dichlorination of donor-acceptor cyclopropanes by iodobenzene dichloride.

Lennart K B Garve¹, Philip Barkawitz, Peter G Jones, Daniel B Werz.

Abstract

Donor-acceptor cyclopropanes are reacted with iodobenzene dichloride to afford ring-opened products bearing chlorine atoms in the 1- and 3-positions, adjacent to the donor and acceptor groups. A variety of different donors (e.g., alkyl, aryl, N, and O) and acceptor moieties (e.g., ketones, diesters, and dinitriles) are used.

Entities: Chemical Species

Year: 2014 PMID： 25337903 DOI： 10.1021/ol5029139

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

12 in total

1. Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation.

Authors: Steven M Banik; Katrina M Mennie; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2017-06-29 Impact factor: 15.419

2. Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors: Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal: European J Org Chem Date: 2021-08-25

3. Fluorinative ring-opening of cyclopropanes by hypervalent iodine reagents. An efficient method for 1,3-oxyfluorination and 1,3-difluorination.

Authors: Nadia O Ilchenko; Martin Hedberg; Kálmán J Szabó
Journal: Chem Sci Date: 2016-09-16 Impact factor: 9.825

4. Ring-Opening 1,3-Aminochalcogenation of Donor-Acceptor Cyclopropanes: A Three-Component Approach.

Authors: André U Augustin; Peter G Jones; Daniel B Werz
Journal: Chemistry Date: 2019-08-07 Impact factor: 5.236

5. Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes.

Authors: Jan Wallbaum; Lennart K B Garve; Peter G Jones; Daniel B Werz
Journal: Chemistry Date: 2016-11-29 Impact factor: 5.236

6. Stereoselective Synthesis of Tropanes via a 6π-Electrocyclic Ring-Opening/ Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles.

Authors: Carina M Sonnleitner; Saerom Park; Robert Eckl; Thomas Ertl; Oliver Reiser
Journal: Angew Chem Int Ed Engl Date: 2020-08-18 Impact factor: 15.336

Ring-opening 1,3-dichlorination of donor-acceptor cyclopropanes by iodobenzene dichloride.

1. Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation.

2. Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

3. Fluorinative ring-opening of cyclopropanes by hypervalent iodine reagents. An efficient method for 1,3-oxyfluorination and 1,3-difluorination.

4. Ring-Opening 1,3-Aminochalcogenation of Donor-Acceptor Cyclopropanes: A Three-Component Approach.

5. Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes.

6. Stereoselective Synthesis of Tropanes via a 6π-Electrocyclic Ring-Opening/ Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles.

7. Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones.

8. Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates.

Review 9. Acetylene in Organic Synthesis: Recent Progress and New Uses.

Review 10. Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.