Stereospecific cyclodimerization of 1-methylphosphole 1-oxide: A theoretical study

György Miklós Keseru, György Keglevich

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18 Citations (Scopus)


PM3 semiempirical calculations on the transition states for the cyclodimerization of 1-methylphosphole oxide (1, Y=Me) suggest the selective formation of product A (2, Y=Me) that is one of the eight possible isomers. Ab initio calculations at the 3-21G* level of theory go even further by justifying the specific formation of isomer A (2, Y=Me) that is the exclusive product of the syntheses. The dimerization seems to be directed by kinetic factors. Calculations on the HOMO-LUMO orbital interactions also confirm the preference for the formation of isomer A (2, Y=Me) where the phosphole rings are joined with the endo fusion and where at both phosphorus atoms the oxygen of the phosphoryl group is projected to the center of the system.

Original languageEnglish
Pages (from-to)166-170
Number of pages5
JournalJournal of Organometallic Chemistry
Issue number2
Publication statusPublished - Sep 5 1999


  • Cyclodimerization
  • Phosphole oxide
  • Semiempirical and ab initio calculations
  • Stereospecificity

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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