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Synthesis of isothiocyanatophosphoranes and isothiocyanatophosphonium salts via oxidative addition of thiocyanogen and ligand substitution: Novel reagents for converting hydroxy groups into thiocyanate and isothiocyanate functions under mild conditions

Burski, J ; Kieszkowski, J ; Michalski, J ; Pakulski, M ; Skowronska, A

Tetrahedron, 1983, Vol.39(24), pp.4175-4181 [Periódico revisado por pares]

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  • Título:
    Synthesis of isothiocyanatophosphoranes and isothiocyanatophosphonium salts via oxidative addition of thiocyanogen and ligand substitution: Novel reagents for converting hydroxy groups into thiocyanate and isothiocyanate functions under mild conditions
  • Autor: Burski, J ; Kieszkowski, J ; Michalski, J ; Pakulski, M ; Skowronska, A
  • Assuntos: Chemistry
  • É parte de: Tetrahedron, 1983, Vol.39(24), pp.4175-4181
  • Descrição: The oxidative addition of thiocyanogen to triphenylphosphine has been investigated by 31P NMR spectroscopy showing the formation of the isothiocyanatophosphonium salt 8. The analogous reaction between thiocyanogen and alkyl o-phenylene phosphites 7 leads to diisothiocyanatophosphoranes 9. The same products were prepared via ligand substitution from the corresponding chlorophosphonium salt 12 and alkyldichloro-o-phenylene phosphóranes 13 by the action of potassium thiocyanate in the presence of 18-crown-6-ether or more conveniently using lead thiocyanate. The phosphonium salt 8 and phosphoranes 9 were employed as convenient novel reagents for converting hydroxy groups into thiocyanate and isothiocyanate functions with high stereoselectivity under very mild conditions. The efficient synthesis of acylisothiocyanales RCONCS, R 2P(O)NCS and R 2P(S)NCS via addition of thiocyanogen to mixed anhydrides is of special interest.
  • Idioma: Inglês

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