The Journal of Organic Chemistry

Metalation-induced double migration of phosphorus from oxygen to carbon. Convenient preparation of bis (2-hydroxyaryl) phosphinic acids

B Dhawan, D Redmore

Index: Dhawan, Balram; Redmore, Derek Journal of Organic Chemistry, 1986 , vol. 51, # 2 p. 179 - 183

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Citation Number: 41

Abstract

Treatment of diary1 ethyl phosphates 8 with lithium diisopropylamide in tetrahydrofuran yields ethyl bis-(2-hydroxyary1) phosphinates 9. The reaction involves the double migration of phosphorus from 0-4 and is probably intramolecular. These phosphinate esters 9 on treatment with trimethylsilyl chloride and sodium iodide in acetonitrile undergo transesterification to give trimethylsilyl esters that yield the corresponding phosphinic ...