Radical cyclization reactions via manganese(III) acetate leading to 2-thienyl-substituted dihydrofuran compounds

Biçer E., YILMAZ M., Karataş M., Pekel A. T.

Helvetica Chimica Acta, cilt.95, sa.5, ss.795-804, 2012 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 95 Sayı: 5
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/hlca.201100397
  • Dergi Adı: Helvetica Chimica Acta
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.795-804
  • Anahtar Kelimeler: 4,5-Dihydrofurans, 2-thienyl-substituted, Cyclization reactions, Manganese(III) acetate, Radical cyclization
  • Ankara Üniversitesi Adresli: Evet

Özet

The 2-thienyl-substituted 4,5-dihydrofuran derivatives 3-8 were obtained by the radical cyclization reaction of 1,3-dicarbonyl compounds 1a-1f with 2-thienyl-substituted conjugated alkenes 2a-2e by using [Mn(OAc) 3] (Tables 1-5). In this study, reactions of 1,3-dicarbonyl compounds 1a-1e with alkenes 2a-2c gave 4,5-dihydrofuran derivatives 3-5 in high yields (Tables 1-3). Also the cyclic alkenes 2d and 2e gave the dihydrobenzofuran compounds, i.e., 6 and 7 in good yields (Table 4). Interestingly, the reaction of benzoylacetone (=1-phenylbutane-1,3-dione; 1f) with some alkenes gave two products due to generation of two stable carbocation intermediates (Table 5). Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.