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, sa.4, ss.291-297, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73 Sayı: 4
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tet.2016.11.061
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.291-297
  • Anahtar Kelimeler: Manganase(III) acetate, Copper(II) acetate, Cycloaddition, Oxidation, Dihydrofurans, Rearrangement, Benzonorbornadiene, Oxabenzonorbornadiene, 1,3-DICARBONYL COMPOUNDS, METAL-SALTS, ACETATE, CYCLIZATIONS, DIHYDROFURANS, DERIVATIVES, MECHANISMS, MN(OAC)(3), ALKENES, KETONES
  • Atatürk Üniversitesi Adresli: Evet

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.