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Carbon atom functionalization via generation of carbanions is the cornerstone of carborane chemistry. In this work, we report the synthesis and structural characterization of free ortho-carboranyl [C2B10H11], a three-dimensional inorganic analog of the elusive phenyl anion that features a “naked” carbanion center. The first example of a stable, discrete C(H)-deprotonated carborane anion was isolated as a completely separated ion pair with a crown ether-encapsulated potassium cation. An analogous approach led to the isolation and structural characterization of a doubly deprotonated 1,1′-bis(o-carborane) anion [C2B10H10]22−, which is the first example of a discrete molecular dicarbanion. These reactive carbanions are key intermediates in carbon vertex chemistry of carborane clusters.

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© The Royal Society of Chemistry 2021

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

APA Citation

H. D. A. Chathumal Jayaweera, Md. Mamdudur Rahman, Pellechia, P. J., Smith, M. A., & Peryshkov, D. V. (2021). Free three-dimensional carborane carbanions. 12(31), 10441–10447.