Regioselectivity observed in manganese(III) acetate mediated addition of acetylacetone to various alkenes: mechanistic and theoretical studies

Date

2016-10-27

Author

Ceyhan, Selin
Cetinkaya, Yasin
Akdağ, Akın
BALCI, METİN

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Various alkenes substituted at the 1,2-positions by 2-thiophenyl, 3-thiophenyl, and phenyl substituted by electron-withdrawing and electron-donating groups were treated with acetylacetone in the presence of Mn(OAc)(3) in acetic acid. In cases where the thiophene ring was connected at the C-2 carbon atom to the double bond, a single regioisomer was formed whereas in case of substitution at the C-3 positions two regioisomers were formed. Stilbene derivatives also gave two regioisomers under the same reaction conditions. However, 1-methoxy-4-(4-nitrostyryl)benzene provided a single cycloaddition product. The observed regioselectivity was discussed in terms of atomic charge distribution on the olefinic double bond carbon atoms. Furthermore, activation barriers for transition states were calculated.

Subject Keywords

Cycloaddition, Substituent effects, Oxidation, Regioselectivity, Mn(OAc)(3)

URI

https://hdl.handle.net/11511/34324

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2016.09.015

Collections

Department of Chemistry, Article

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Citation Formats

S. Ceyhan, Y. Cetinkaya, A. Akdağ, and M. BALCI, “Regioselectivity observed in manganese(III) acetate mediated addition of acetylacetone to various alkenes: mechanistic and theoretical studies,” TETRAHEDRON, pp. 6815–6824, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/34324.