Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies

Ali, Mohamed Fadelalla; Caliskan, Rasit Ali; Şahin, Ertan; Balci, Metin

doi:10.1016/j.tet.2008.12.012

Makale Tam Makale Uluslararası 2009

Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies

Mohamed Fadelalla Ali, Rasit Ali Caliskan, Ertan Şahin, Metin Balci

TETRAHEDRON Cilt 65 · Sayı 7 · ss. 1430–1437 · 14.02.2009

DOI ile aç

Özet

Homobenzonorbornadiene and benzobarrelene were reacted with dimedone/acetylacetone and Mn(OAc)(3) in the presence of Cu(OAc)(2) in acetic acid. Mainly rearranged products having a [2.2.2]skeleton and the nonrearranged dihydrofuran derivatives were obtained. These observations clearly indicated that the second oxidation takes place before the cyclization reaction. Furthermore, intramolecular tandem oxidations were observed where unusually oxyl radicals attack the double bond to form the products. The mechanism of the formation of the products is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

Anahtar kelimeler

Free radicals DERIVATIVES benzonorbornadiene HIGH-TEMPERATURE BROMINATION Rearrangement Cycloaddition Manganese triacetate Homobenzonorbornadiene Benzobarrelene GAMMA-LACTONES METAL-SALTS BETA-DIESTERS ACETIC-ACID CYCLIZATIONS ACETATE ANNULATION

Atıf için künye

Ali, M. F., Caliskan, R. A., Şahin, E., & Balci, M. (2009). Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies. TETRAHEDRON, 65(7), 1430–1437. https://doi.org/10.1016/j.tet.2008.12.012

BibTeX

@article{ali2009-66634,
  author = {Ali, Mohamed Fadelalla and Caliskan, Rasit Ali and Şahin, Ertan and Balci, Metin},
  title = {Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies},
  journal = {TETRAHEDRON},
  year = {2009},
  volume = {65},
  number = {7},
  pages = {1430--1437},
  issn = {0040-4020},
  doi = {10.1016/j.tet.2008.12.012},
  url = {https://akademik.atauni.edu.tr/yayinlar/66634-manganeseiii-mediated-oxidative-free-radical-additions-of-13-dicarbonyl}
}