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Updated: Apr 27, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
One-, two-, and three-electron reduction of a cyclic alkyl(amino)carbene-SbCl₃ adduct
Robert Kretschmer1, David A Ruiz, Curtis E Moore
1UCSD-CNRS Joint Research Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA) http://bertrandgroup.ucsd.edu.
Abstract:
A cyclic alkyl(amino)carbene readily reacts with SbCl3 to form the corresponding Sb(III) adduct. One-electron reduction gives rise to the first example of a neutral antimony-centered radical characterized in solution. Two-electron reduction affords a Lewis base stabilized chloro-stibinidene, whereas three-electron reduction gives an antimony diatomic species capped by two carbenes. The radical has been characterized by EPR spectroscopy, while the structure of the other three species has been ascertained by single-crystal X-ray diffraction. In these four species, the formal oxidation state of the metalloid diminishes from III, to II, to I, and finally 0.
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