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


ÇALIŞKAN R. , Nohut N. , YILIMAZ O., ŞAHİN E., Balci M.

TETRAHEDRON, cilt.73, ss.291-297, 2017 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 73 Konu: 4
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tet.2016.11.061
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.291-297

Özet

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. (C) 2016 Elsevier Ltd. All rights reserved.