P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones

The synthesis, structure and reactivity of the fluoroaryl phosphinic acid HF(4)C(6)–P(O)HOH is reported and compared to a sterically comparable yet non-fluorinated analog with similar size. The fluoroaryl phosphinic acid undergoes reversible P–H addition to the carbonyl functionality of ketones unde...

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Detalles Bibliográficos
Autores principales: Orthaber, Andreas, Albering, Jörg H., Belaj, Ferdinand, Pietschnig, Rudolf
Formato: Texto
Lenguaje:English
Publicado: Elsevier Sequoia Sa 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2954306/
https://www.ncbi.nlm.nih.gov/pubmed/21072125
http://dx.doi.org/10.1016/j.jfluchem.2010.07.008
Descripción
Sumario:The synthesis, structure and reactivity of the fluoroaryl phosphinic acid HF(4)C(6)–P(O)HOH is reported and compared to a sterically comparable yet non-fluorinated analog with similar size. The fluoroaryl phosphinic acid undergoes reversible P–H addition to the carbonyl functionality of ketones under formation of a P–C bond which is retained in the resulting α-hydroxy phosphinic acid. The latter shows an extended 2D hydrogen bonded network in the solid state.

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