Organic Chemistry

Making a triple negative

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Science  22 Jun 2018:
Vol. 360, Issue 6395, pp. 1311
DOI: 10.1126/science.360.6395.1311-b

The trifluoromethanesulfonyl (Tf) group is remarkably adept at stabilizing negative charge: It boasts highly withdrawing fluorines and sulfur-oxygen bonds that can delocalize electrons through resonance. Höfler et al. took full advantage of these properties in generating a molecule with three independent anionic carbon centers. The synthetic reaction coupled triformylmethane with three equivalents of Tf2CH2, after which a base deprotonated all three Tf-substituted carbon centers. The compound was characterized by crystallography and showed trigonal-planar geometries at each charged carbon.

Angew. Chem. Int. Ed. 10.1002/anie.201803647 (2018).

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