C-C Bond Activation and Demethylenation of Epoxides by Amine Radical Dications.

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
02 Jun 2023
Historique:
medline: 9 5 2023
pubmed: 9 5 2023
entrez: 9 5 2023
Statut: ppublish

Résumé

In this note, we explore a unique reactivity pattern that involves a rare radical-based C-C bond scission of epoxides followed by demethylenation. The reaction is accomplished by Selecfluor and its radical dication working in tandem; a mechanism supported by experiment and DFT calculations is proposed that involves the generation and identification of a key reactive intermediate. The reaction seems to be fairly general for 1,1-disubstituted epoxides.

Identifiants

DOI: 10.1021/acs.joc.3c00605 PMID: 37159569
pubmed: 37159569
doi: 10.1021/acs.joc.3c00605
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

7597-7600

Auteurs

Eric Holt (E)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.
ORCID: 0000-0003-2068-6962

Nathaniel G Garrison (NG)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Rozhin Rowshanpour (R)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Justin Jeeyoung Kim (JJ)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Nicolas Henriquez (N)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Winson Lam (W)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Neil Kiame (N)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Jack Williams (J)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Sherrie Zhao (S)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.

Travis Dudding (T)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.
ORCID: 0000-0002-2239-0818

Thomas Lectka (T)

Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Department of Chemistry, Brock University, St. Catharines, Ontario L2S3A1, Canada.
ORCID: 0000-0003-3088-6714

Classifications MeSH