We are developing anthracene-based reagents for phosphinidene transfer reactions. Bicyclic compounds having the formula RPA (A = C14H10 or anthracene) can serve to transfer the [RP] group either thermally, if the substituent is a strong π donor, or by metal-mediated processes. Phosphinidene transfer to olefins results in the formation of three-membered phosphirane rings, a process analogous to olefin epoxidation. Phosphinidene transfer to transition metal complexes results in phosphinidene complexes, as we demonstrate in the formation of a series of terminal ruthenium phosphinidene complexes having very short ruthenium-phosphorus double bonds. For RPA compounds that are thermally stable, such as tBuPA, phosphinidene transfer to olefins can be accomplished in a metal-mediated process to produce phosphiranes such as styrene-derived tBuPCH2CHPh, obtained as a single diastereomer, which is of interest for its possible utility as a ligand for transition metals. Mechanistic aspects of the phosphinidene transfer reactivity will be discussed.

Phosphinidene transfer reactions of anthracene-supported phosphinidene transfer reagents

2019 Spring National Meeting

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