Perfluoroalkyl Grignard Reagents: NMR Study of 1-Heptafluoropropylmagnesium Chloride in Solution

Jie Guang; Russell Hopson; Paul G Williard; Motohiro Fujiu; Kazuyuki Negishi; Koichi Mikami

doi:10.1021/acs.joc.6b00807

Perfluoroalkyl Grignard Reagents: NMR Study of 1-Heptafluoropropylmagnesium Chloride in Solution

J Org Chem. 2016 Jul 15;81(14):5922-8. doi: 10.1021/acs.joc.6b00807. Epub 2016 Jun 28.

Authors

Jie Guang¹, Russell Hopson¹, Paul G Williard¹, Motohiro Fujiu², Kazuyuki Negishi², Koichi Mikami²

Affiliations

¹ Department of Chemistry, Brown University , Providence, Rhode Island 02912, United States.
² Department of Applied Chemistry, Tokyo Institute of Technology , Tokyo 152-8552, Japan.

PMID: 27295419
DOI: 10.1021/acs.joc.6b00807

Abstract

We report on the generation of a perfluoroalkyl Grignard reagent ((F)RMgX) by exchange reaction between a perfluoroalkyl iodide ((F)R-I) and a Grignard reagent (RMgX). (19)F NMR was applied to monitor the generation of n-C3F7MgCl. Additional NMR techniques, including (19)F COSY, NOESY, and pulsed gradient spin-echo (PGSE) diffusion NMR, were invoked to assign peaks observed in (19)F spectrum. Schlenk equilibrium was observed and was significantly influenced by solvent, diethyl ether, or THF.

Publication types

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