136829-79-3Relevant academic research and scientific papers
METALATION INDUCED REARRANGEMENT OF DI-t-BUTYL(3-SUBSTITUTED PHENYL)PHOSPHATES
Dhawan, Balram,Redmore, Derek
, p. 183 - 187 (2007/10/02)
Treatment of di-t-butyl(3,5-dimethylphenyl)phosphate 1b with lithium diisopropylamide at -78 deg C followed by warming to rt yields di-t-butyl(2-hydroxy-4,6-dimethylphenyl)phosphonate 2b.Di-t-butyl(3-methoxyphenyl)phosphate 1c on similar treatment with LDA yields di-t-butyl(2-hydroxy-6-methoxyphenyl)phosphonate 2c.Similarly di-t-butyl(3,5-dimethyloxyphenyl)phosphate 1d rearranges to di-t-butyl(2-hydroxy-4,6-dimethoxyphenyl)phosphonate 2d.Di-t-butyl(2-di-t-butoxyphosphinyl-3,5-dimethoxyphenyl)phosphate 3, when treated with LDA, yields tetra-t-butyl(2-hydroxy-4,6-dimethoxy-1,3-phenylene)bis(phosphonate) 4.The phosphonates 2c and 2d on treatment with trifluoroacetic acid in toluene are converted into the corresponding phosphonic acids 2e and 2f respectively. Key words: Lithiation; phosphate-phosphonate rearrangement; phosphonic acids.
