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Updated: Jul 10, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
[1-H2N-CB11F11]---synthesis and reactions of a functionalized fluorinated carbadodecaborate anion
Maik Finze1, Guido J Reiss, Manfred Zähres
1Institut für Anorganische Chemie und Strukturchemie II, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany. maik.finze@uni-duesseldorf.de
Abstract:
In anhydrous hydrogen fluoride, K[1-H2N-CB11H11] is fluorinated with elemental fluorine to produce K[1-H2N-CB11F11]. Under strong alkaline conditions, two fluorine atoms of the [1-H2N-CB11F11]- anion are regioselectively exchanged, yielding the [1-H2N-4,6-(HO)2-CB11F9]- anion via [1-H2N-6-HO-CB11F10]- as an intermediate. Both hydroxycarborate anions were isolated as [Ph4P]+ salts. All of the species were characterized by IR, Raman, and multi-NMR spectroscopy, thermal analysis (DSC) as well as by mass spectrometry (MALDI). The assignment of the NMR signals was supported by DFT calculations. Solid-state structures of K[1-H2N-CB11F11], [BzPh3P][1-H2N-CB11F11], [Ph4P][1-H2N-4,6-(HO)2-CB11F9], [Ph4P][1-H2N-6-HO-CB11F10], and [BzPh3P][1-H2N-CB11H11] were determined by single-crystal X-ray diffraction.
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