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Updated: Oct 22, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Free three-dimensional carborane carbanions
H D A Chathumal Jayaweera1, Md Mamdudur Rahman1, Perry J Pellechia1
1Department of Chemistry and Biochemistry, University of South Carolina 631 Sumter St. Columbia South Carolina 29208 USA peryshkov@sc.edu.
Abstract:
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]2 2-, 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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