Synthesis and characterization of a novel N-F reagent derived from the ethano-Tröger's base: (1)J(FN) coupling constants as a signature for the N-F bond

Raul Pereira; Jamie Wolstenhulme; Graham Sandford; Timothy D W Claridge; Véronique Gouverneur; Ján Cvengroš

doi:10.1039/c5cc08375c

Synthesis and characterization of a novel N-F reagent derived from the ethano-Tröger's base: (1)J(FN) coupling constants as a signature for the N-F bond

Chem Commun (Camb). 2016 Jan 28;52(8):1606-9. doi: 10.1039/c5cc08375c. Epub 2015 Dec 11.

Authors

Raul Pereira¹, Jamie Wolstenhulme, Graham Sandford, Timothy D W Claridge, Véronique Gouverneur, Ján Cvengroš

Affiliation

¹ Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, UK. veronique.gouverneur@chem.ox.ac.uk.

PMID: 26658721
DOI: 10.1039/c5cc08375c

Abstract

Methylation of 2,8-dimethyl-6H,12H-5,11-ethanodibenzo[b,f][1,5]-diazocine (ethano-Tröger's base) with methyl iodide followed by ion metathesis and fluorination with N-fluoro-2,3,4,5,6-pentachloropyridinium triflate affords a new electrophilic N-F reagent, that is more reactive than Selectfluor. 2D (19)F-(15)N HMQC experiments provide (1)JNF coupling constants which are diagnostic for the N-F functional group.

Publication types

Research Support, Non-U.S. Gov't