Photocycloaddition of acetylacetonatoboron derivatives with simple olefins

Photocycloaddition of acetylacetonatoboron derivatives with simple olefins 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Photocycloaddition of acetylacetonatoboron derivatives with simple olefins

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Publisher
Brill Academic Publishers
Copyright
Copyright © 2002 by VSP 2002
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/15685670260188629
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 13, 2004

References

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