A Striking Mode of Activation of Carbon Disulfide with a Cooperative Bis(silylene)

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Abstract

The reactivity of the 1,4-substituted bis(silylenyl)terphenylene 1, 1,4-[ortho-(LSi)C6H4]2C6H4, (L=RC(NtBu)2, R=Ph, Mes) towards CS2 is reported. It results in a dearomatization of the phenylene ring, affording the 1,3-substituted cyclohexadiene derivative 2. According to DFT calculations, a transient silene containing a Si=C bond capable of π(C=C) addition at the aromatic phenylene ring is a key intermediate. In contrast, addition of CS2 to the biphenyl-substituted mono-silylene ortho-(LSi)C6H4-C6H5 3 leaves the aromatic π-system intact and forms, in a [1+2] cycloaddition reaction, the corresponding thiasilirane 4 with a three-membered SiSC ring. Further experimental studies led to the isolation of the novel mesoionic five-membered Si2S2C heterocycle 6, which reacts with CS2 under C−C bond formation. All isolated new compounds were fully characterized and their molecular structures determined by single-crystal X-ray diffraction analyses.

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Luecke, M. P., Giarrana, L., Kostenko, A., Gensch, T., Yao, S., & Driess, M. (2022). A Striking Mode of Activation of Carbon Disulfide with a Cooperative Bis(silylene). Angewandte Chemie - International Edition, 61(2). https://doi.org/10.1002/anie.202110398

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