3d-Orbital Resonance in Trivalent Organophosphines. I. Metalation of Methylphosphines

DJ Peterson, HR Hays

Index: Peterson,D.J.; Hays,H.R. Journal of Organic Chemistry, 1965 , vol. 30, p. 1939 - 1942

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Citation Number: 49

Abstract

Alkyllithium compounds selectively metalate methyldiphenylphosphine, dimethylphenylphosphine, and di-n-hexylmethylphosphine on a methyl carbon atom to give the corresponding phosphino carbanions in yields ranging from 14-54%. The relative rates of metalation of dimethyldodecylphosphine to dimethyldodecylamine have been found to be ca. 15: 1. The enhanced rates of metalation of the methylphosphines provide evidence for ...