4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 14, Pages 5922-5928

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00807

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Funding

  1. NSF grant [1058051]
  2. Japan Science and Technology Agency (JST) (ACT-C: Advanced Catalytic Transformation for Carbon Utilization)

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

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