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.
- Phosphole oxide
- Semiempirical and ab initio calculations
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry