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

2017-01-26
ÇALIŞKAN, Raşit
Nohut, Neslihan
Yilimaz, Ozlem
ŞAHİN, Ertan
Balcı, Metin
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.
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, vol. 73, no. 4, pp. 291–297, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56733.