22472-42-0Relevant academic research and scientific papers
Organolithium displacement of aryl anions from tertiary phosphine derivatives of diphenyl ether
Levy, Jack B.,Walton, Richard C.,Olsen, Ron E.,Symmes Jr., Courtland
, p. 545 - 548 (1996)
Methyllithium displaces a phenyl anion from 10-phenyl-10H-phenoxaphosphine to produce a 70:30 mixture of 10-methyl-10H-phenoxaphosphine and starting phosphine. Butyllithium gives 50% conversion to 10-butyl-10H-phenoxaphosphine. These reactions could take place either by a one-step nucleophilic displacement or by ring cleavage followed by recyclization. To show the feasibility of the two-step process, non-heterocyclic lithiated tertiary phosphines were generated and shown to cyclize to phenoxaphosphines. For example, reaction of 2-phenoxyphenyldiphenylphospnine with phenyllithium produced 10-phenyl-10H-phenoxaphosphine (by lithiation ortho to oxygen followed by cyclization) along with triphenylphosphine (by direct displacement of 2-lithiodiphenyl ether). Other compounds prepared in this work: 2,2′-bis(diphenylphosphino)-diphenyl ether, bis(2-phenoxyphenyl)phenylphospnine, tris(2-phenoxyphenyl)phosphine, 4-carboxy-10-phenyl-10H-phenoxaphosphine, and the oxides and sulfides of the phosphines.
