Phosphine oxides, commonplace within chemistry, exist as monomeric species featuring the phosphoryl functional group (P=O/P+–O–). Arsine oxides, although somewhat more prone to reduction, are also stable monomeric species featuring a tetrahedrally substituted pnictogen center. In contrast, stibine oxides are polymeric and there are no known examples of the unperturbed stiboryl group (Sb=O/Sb+–O–). An overview of our approach to tackling this problem will be presented. We now report the isolation of the first monomeric stibine oxide, Dipp3SbO (where Dipp = 2,6-diisopropylphenyl). Spectroscopic, diffractometric, and computational studies provide insight into the nature of the Sb=O/Sb+–O– bond. Moreover, isolation of Dipp3SbO allows the chemistry of the stiboryl group to be explored for the first time, permitting an expansion of a periodic trend in pnictogen chemistry that has remained elusive for over a century.

Kinetic stabilization of the stiboryl group: Isolation and characterization of the first monomeric stibine oxide

ACS Spring 2022

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