Bulky phosphines and their redox properties have received increased attention in the view of useful auxiliary ligands for transition metal catalysts and Lewis-base components of frustrated Lewis pairs for chemical transformations. Herein we report the synthesis, structure, and properties of a series of trialkylphosphines (R = methyl, ethyl, isopropyl, -butyl, 1-adamantyl) that possess the bulky 2,2,5,5-tetrakis(trimethylsilyl)-1-phosphacyclopentane as a structural backbone. Among these phosphines, , which contains an adamantyl moiety, has a very large buried volume (%) for a trialkylphosphine (62.0) and shows a quasi-reversible oxidative wave at a lower oxidation potential (-0.12 V in CHCl, vs ferrocene/ferrocenium couple) by cyclic voltammetry. The reaction of with AgPF afforded a cationic silver aquo complex [Ag()(HO)][PF], whereas the reaction with NOSbF gave a persistent phosphine radical cation []. Based on the EPR spectra and DFT studies, the spin and positive charge of [] are localized on the phosphorus atom.
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