The epimetallation and carbonation of carbonyl and imino derivatives: Epivanadation route to 2-amino and 2-hydroxy acids |
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Authors: | John J Eisch Paul O Fregene |
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Institution: | a Department of Chemistry, The State University of New York at Binghamton, Binghamton, NY 13902-6000, USA b Chemistry Department, Drake University, 207 University Avenue, Des Moines, Iowa 50311, USA |
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Abstract: | The feasibility of hydrocarboxylating carbonyl and imino derivatives by the two-step process of epimetallation and carbonation has been demonstrated with the model substrates of 9-fluorenone and 9-fluorenone anil. With lithium vanadium dihydride as the epimetallating agent, such hydrocarboxylation has led to a 75% yield of 9-hydroxy-9-fluorenecarboxylic acid and a 65% yield of 9-(N-phenylamino)-9-fluorenecarboxylic acid, respectively. Some initial success in extending the scope of this reaction to other substrates, such as benzophenone, has been achieved by using other epimetallating agents, like the presumed LiV(CH3)2 and Ti(OPri)2. A brief review of the processes and organic synthetic applications of epimetallation and transfer epimetallation of C-C π-bonds is offered as background. |
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Keywords: | Hydrocarboxylation Epimetallation of C length as m-dash" src="http://cdn els-cdn E bond (E " target="_blank">com/sd/entities/dbnd" class="glyphImg">E bond (E = O N-R) Carbonation Lithium vanadium(I) dihydride Presumed lithium dimethylvanadate(I) |
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