Electron spin resonance study of phosphoranyl radicals : I. influence of steric and electronic effects on radical formation in solution

A.E.H. de Keijzer, H.M. Buck

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Abstract

An electron spin resonance study of phosphoranyl radicals, generated by u.v. irradiation of solutions containing a trialkylphosphite and a dialkylperoxide, enabled us to examine the influence of steric and electronic factors on radical formation. It was demonstrated that the influence of steric factors, such as a- or ß-branching of the alkyl groups, on the magnitude of radical formation was present in both trialkyl- and methyldialkylphosphites, but not in dimethylalkylphosphites. Furthermore, the study of additional hetero atoms in the alkyl ligand of the dimethylalkylphosphites clearly revealed the influence of the gauche-effect. It was demonstrated that the presence of the gauche-effect, which causes a conformational preference in which a larger steric hindrance is produced, resulted in a decrease of radical formation.
Original languageEnglish
Pages (from-to)203-214
JournalPhosphorus and Sulfur and the Related Elements
Volume31
Issue number3-4
DOIs
Publication statusPublished - 1987

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