Mn(OAc)(3)-promoted sulfur-directed addition of an active methylene compound to alkenes

DELIOMEROGLU M. K., DENGİZ Ç., CALISKAN R., BALCI M.

TETRAHEDRON, cilt.68, sa.29, ss.5838-5844, 2012 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 68 Sayı: 29
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1016/j.tet.2012.05.003
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5838-5844
  • Anahtar Kelimeler: Manganese(III) acetate, Cyclization, Dihydrofuran, Thiophene, Furan, MANGANESE(III) ACETATE, OXIDATIVE CYCLIZATION, GENERAL HYPOTHESIS, GAMMA-LACTONES, 3-OXOPROPANENITRILES, 3-CYANO-4,5-DIHYDROFURANS, MECHANISM
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Various alkenes substituted at the 1,2-positions by phenyl, thiophene and furan rings were reacted with 3-(4-methoxyphenyl)-3-oxopropanenitrile in the presence of Mn(OAc)(3)center dot 2H(2)O. The exact structure and configuration of the dihydrofuran derivatives formed were determined. In all cases only one regioisomer was formed. The observed regioselectivity was explained on the basis of the formation of a complex between Mn(OAc)(3), alkene, and 3-(4-methoxyphenyl)-3-oxopropanenitrile, which directs the mode of the addition to the double bond. (C) 2012 Elsevier Ltd. All rights reserved.