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Metal-Catalyzed Thermal Reactions of Cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes

Author:
Bosnidou, Alexandra-Eleni, Kalpogiannaki, Dimitra, Karanestora, Sofia, Nixas, John A., Hadjiarapoglou, Lazaros P.
Source:
Journal of organic chemistry 2015 v.80 no.2 pp. 1279-1283
ISSN:
1520-6904
Subject:
catalytic activity, chemical reactions, chemical structure, organic chemistry, organic compounds, regioselectivity
Abstract:
A cyclic β-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh₂(OAc)₄ catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.
Agid:
5504697