Bulky ylide-substituted phosphines have recently found application as potent ligands in homogeneous catalysis. The attempted synthesis of the ylide-substituted fluorenylphosphine Y P(Cy)Flu [Y =Cy P(Ph)C; Flu=9-methylfluorenyl] now resulted in the unexpected elimination of 9-methylenefluorene during the deprotonation step of the intermediary α-phosphino phosphonium salt to yield the secondary ylide-substituted phosphine Y P(Cy)H. This phosphine underwent formal H elimination under basic conditions to form a cyclic phosphonium ylide with a P-C-P-C four-membered ring via deprotonation of one cyclohexyl group of the PCy moiety. Upon coordination to transition metals the secondary ylidylphosphine forms a neutral phosphide ligand by shift of the proton into the ylide-backbone and formation of zwitterionic metal complexes.
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