Single‐Step Gas‐Phase Polyperfluoroalkylation of Naphthalene Leads to Thermodynamic Products |
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| Authors: | Long K San Eric V Bukovsky Dr Igor V Kuvychko Dr Alexey A Popov Prof Steven H Strauss Dr Olga V Boltalina |
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| Institution: | 1. Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA);2. Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany) |
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| Abstract: | High‐temperature gas‐phase, solvent‐ and catalyst‐free reaction of naphthalene with an excess of RFI reagent (RF?CF3, C2F5, n‐C3F7, and n‐C4F9) was used for the first time to produce a series of highly perfluoroalkylated naphthalene products NAPH(RF)n with n=2–5. Four 95+ % pure 1,3,5,7‐NAPH(RF)4 with RF?CF3, C2F5, n‐C3F7, and n‐C4F9 were isolated using a simple chromatography‐free procedure. These new compounds were fully characterized by 19F and 1H NMR spectroscopy, X‐ray crystallography (for RF?CF3 and C2F5), atmospheric‐pressure chemical ionization mass spectrometry, and cyclic and square‐wave voltammetry. DFT calculations confirm that the proposed synthesis yields the most stable isomers that have not been accessed by alternative preparation techniques. |
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| Keywords: | density functional calculations electron acceptors naphthalene perfluoroalkyl iodides perfluoroalkylation |
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