Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene

Date

2017-01-26

Author

ÇALIŞKAN, Raşit
Nohut, Neslihan
Yilimaz, Ozlem
ŞAHİN, Ertan
Balcı, Metin

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Benzonorbornadiene and 7-oxabenzonorbornadiene were reacted with Meldrum's acid and dimethyl malonate in the presence of Mn(OAc)(3) and Cu(OAc)(2) in acetic acid. The reaction of benzonorbornadiene with Meldrum's acid gave a naphthalene derivative whereas the reaction with dimethyl malonate formed rearranged products derived from a carbocation intermediate. However, the reaction of 7-oxabenzonorbornadiene with Meldrum's acid gave two nonrearranged products. On the other hand, the reaction with dimethyl malonate unexpectedly formed a dihydronapthalene derivative with an unusual structure. The mechanism for the formation of the products is discussed.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/56733

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2016.11.061

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

R. ÇALIŞKAN, N. Nohut, O. Yilimaz, E. ŞAHİN, and M. Balcı, “Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum’s acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene,” TETRAHEDRON, pp. 291–297, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56733.