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Issue 8, 2016
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Synthesis and characterization of a novel N–F reagent derived from the ethano-Tröger's base: 1JFN coupling constants as a signature for the N–F bond

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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 19F–15N HMQC experiments provide 1JNF coupling constants which are diagnostic for the N–F functional group.

Graphical abstract: Synthesis and characterization of a novel N–F reagent derived from the ethano-Tröger's base: 1JFN coupling constants as a signature for the N–F bond

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Supplementary files

Article information


Submitted
08 Oct 2015
Accepted
24 Nov 2015
First published
25 Nov 2015

Chem. Commun., 2016,52, 1606-1609
Article type
Communication
Author version available

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

R. Pereira, J. Wolstenhulme, G. Sandford, T. D. W. Claridge, V. Gouverneur and J. Cvengroš, Chem. Commun., 2016, 52, 1606
DOI: 10.1039/C5CC08375C

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