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Updated: Oct 26, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Carbene-Stabilized Dithiolene (L0 ) Zwitterions
Yuzhong Wang1, Phuong M Tran1, Yaoming Xie1
1Department of Chemistry, Center for Computational Chemistry, and Complex Carbohydrate Research Center, The University of Georgia, Athens, GA, 30602-2556, USA.
Abstract:
A series of reactions between Lewis bases and an imidazole-based dithione dimer (1) has been investigated. Both cyclic(alkyl)(amino)carbene (CAAC) (2) and N-heterocyclic carbene (NHC) (4), in addition to N-heterocyclic silylene (NHSi) (6), demonstrate the capability to cleave the sulphur-sulphur bonds in 1, giving carbene-stabilized dithiolene (L0 ) zwitterions (3 and 5) and a spirocyclic silicon-dithiolene compound (7), respectively. The bonding nature of 3, 5, and 7 are probed by both experimental and theoretical methods.
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