Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 27, Pages 6922-6926Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800828
Keywords
bis-silylcarbenoid; bulky substituents; heterocumulenes; sulfur; X-ray crystallography
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Bis(methylene)-lambda(4)-sulfane 1, a >C=S=C< heterocumulene, was obtained as a red crystalline solid from the reaction between elemental sulfur and a carbenoid that contains sterically demanding silylalkyl groups. Under atmospheric conditions, and even at elevated temperatures, 1 exhibits extraordinary stability. The molecular structure and electron-density distribution of 1 were analyzed by single-crystal X-ray diffraction analysis, which revealed a bent C=S=C geometry with C=S=C -bonds. These results, combined with those of variable-temperature NMR measurements and theoretical calculations suggest a slow rotation of the S=C moieties in 1, the stability and structure of which were further examined by theoretical calculations.
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