Photocycloaddition of acetylacetonatoboron derivatives with simple olefins

Autor:	Yu-Huang Zhang, Yuan L. Chow, Kuniaki Itoh, Jin-Pei Cheng, Dabin Gao, Yu Chang
Rok vydání:	2002
Předmět:	chemistry.chemical_compound Electron transfer chemistry Radical ion Difluoride Ether General Chemistry Singlet state Methylene Photochemistry Cycloaddition Oxalate
Zdroj:	Research on Chemical Intermediates. 28:313-327
ISSN:	1568-5675 0922-6168
DOI:	10.1163/15685670260188629
Popis:	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.
Databáze:	OpenAIRE
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