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

ÇALIŞKAN, Raşit; Nohut, Neslihan; Yilimaz, Ozlem; Şahin, Ertan; Balci, Metin

doi:10.1016/j.tet.2016.11.061

Makale Tam Makale Uluslararası 2017

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

Raşit ÇALIŞKAN, Neslihan Nohut, Ozlem Yilimaz, Ertan Şahin, Metin Balci

TETRAHEDRON Cilt 73 · Sayı 4 · ss. 291–297 · 26.01.2017

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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.

Anahtar kelimeler

MECHANISMS DERIVATIVES 1 KETONES oxidation benzonorbornadiene Alkenes Rearrangement Cycloaddition METAL-SALTS CYCLIZATIONS ACETATE Manganase(III) acetate Copper(II) acetate Dihydrofurans Oxabenzonorbornadiene 3-DICARBONYL COMPOUNDS MN(OAC)(3)

Atıf için künye

ÇALIŞKAN, R., Nohut, N., Yilimaz, O., Şahin, E., & Balci, M. (2017). Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene. TETRAHEDRON, 73(4), 291–297. https://doi.org/10.1016/j.tet.2016.11.061

BibTeX

@article{caliskan2017-66667,
  author = {ÇALIŞKAN, Raşit and Nohut, Neslihan and Yilimaz, Ozlem and Şahin, Ertan and Balci, Metin},
  title = {Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene},
  journal = {TETRAHEDRON},
  year = {2017},
  volume = {73},
  number = {4},
  pages = {291--297},
  issn = {0040-4020},
  doi = {10.1016/j.tet.2016.11.061},
  url = {https://akademik.atauni.edu.tr/yayinlar/66667-unusual-manganeseiii-mediated-oxidative-free-radical-additions-of-meldrums-acid}
}