Phosphaenones, like their carbon analogue enones (C=C–C=O), are promising building blocks for synthetic chemistry and materials science. However, in contrast to the α- and β-phosphaenones, structurally and spectroscopically well-defined diphosphaenones (DPEs) are rare. In this study, we disclose the isolation and spectroscopic characterization of N-heterocyclic vinyl (NHV) substituted acyclic DPEs 3a,b [NHV–P=P–C(O)–NHV]. X-ray diffraction methods allowed to determine the structures, which show a central planar trans P=P–C=O configuration. Compound 3a behaves like classical enones and shows 1,4-addition across the P=P–C=O unit, which proceeds in a stepwise manner. In contrast, 3a exhibits also 1,2-addition across the P=P but not the C=O double bond, which differentiates it from enones.

This article is Open Access

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