Research on Chemical Intermediates

, Volume 28, Issue 4, pp 313–327 | Cite as

Photocycloaddition of acetylacetonatoboron derivatives with simple olefins

  • Yu-Huang Zhang
  • Kuniaki Itoh
  • Dabin Gao
  • Yu Chang
  • Jin-Pei Cheng
  • Yuan L. Chow
Article

Abstract

Acetylacetonatoboron difluoride (AABF2) and oxalate (AABO) undergo cycloaddition from their singlet excited state with cyclic and terminal olefins to give stereospecific but non-regiospecific products; the latter oxalate reacted slightly faster than the former difluoride. A conjugated diene, 1,3-cyclooctadiene, and methyl substituted benzenes also reacted similarly but with slower rates owing to electron transfer at the encounter stage. The resulting radical ion pairs may undergo radical ion type reactions and/or reverse electron transfer, which leads to the partial waste of the photoenergy. For the same reasons, the reaction occurs more efficiently in non-polar solvents, such as ether, dioxane and methylene chloride than in acetonitrile.

1,3-DIKETONATOBORATES SINGLET EXCITED STATE PHOTOCYCLOADDITION EXCITED STATE ELECTRON TRANSFER MODIFIED DE MAYO REACTION SOLVENT EFFECTS ON EXCIPLEX FORMATION 

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Copyright information

© VSP 2002 2002

Authors and Affiliations

  • Yu-Huang Zhang
  • Kuniaki Itoh
  • Dabin Gao
  • Yu Chang
  • Jin-Pei Cheng
  • Yuan L. Chow

There are no affiliations available

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