Diels-Alder cycloadditions of 1,2-dihydrophosphinine oxides and fragmentation-related phosphorylations with 2-phosphabicyclo[2.2.2]octadiene oxides under green chemical conditions-the role of microwave and ionic liquids

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Abstract

The effect of the use of microwave (MW) and solvents including ionic liquids on the Diels-Alder reaction of 1,2-dihydrophosphinine oxides (1) and fragmentation-related phosphorylation of phenols with 2-phosphabicyclo[2.2.2] octadiene oxides (4) was studied. The MW-assisted Diels-Alder reaction of dihydrophosphinine oxides (1) with N-phenylmaleimide may be advantageous to carry out in [bmim][BF 4] due to shorter reaction times, but the dimerization of the double-bond isomers (A and B) of the dihydrophosphinine oxides (1) may be best accomplished under MW in the absence of any solvent. The fragmentation-related phosphorylations may also be carried out under MW, which with the P-phenyl precursor (4a) became more efficient in [bmim][BF 4].

Original languageEnglish
Pages (from-to)2172-2179
Number of pages8
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume186
Issue number11
DOIs
Publication statusPublished - Dec 1 2011

Keywords

  • Diels-Alder reaction
  • Fragmentationrelated phosphorylation
  • Ionic liquid
  • Microwave
  • P-heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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