Phospha-Michael reactions involving P-heterocyclic nucleophiles

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Abstract

P-heterocyclic γ-ketophosphonates were synthesized by the Michael reaction of methyl vinyl ketone with dibenzo-1,2-oxaphosphorine 2-oxide, 1,3,2-dioxaphosphorine 2-oxide and benzo1,3,2-dioxaphospholane 2-oxide, respectively. In the first two cases, 50% of 1,8-diazabicyclo[5.4.0]undec7-ene had to be used that was also required in the addition of dibenzooxaphosphorine oxide to cyclohexenone to result in the formation of the corresponding y-ketophosphonate. The addition of dibenzooxaphosphorine oxide to less reactive 1,2-dihydrophosphinine oxide was accomplished after activation by an equimolar amount of trimethylaluminum to afford a 3-P(O) <-1,2,3,6- tetrahydrophosphinine oxide, which was subjected to catalytic hydrogenation to provide the corresponding 1,2,3,4,5,6-hexahydrophosphinine oxide.

Original languageEnglish
Pages (from-to)288-292
Number of pages5
JournalHeteroatom Chemistry
Volume19
Issue number3
DOIs
Publication statusPublished - Apr 22 2008

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ASJC Scopus subject areas

  • Chemistry(all)

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