Synthesis of cyclohexane derivatives including Br, Cl, N, O, and S at 1,2,4,5-positions: selectivity in addition reactions

KAYA A. A., MENZEK A., ŞAHİN E.

TETRAHEDRON, cilt.70, sa.1, ss.83-91, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 70 Sayı: 1
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tet.2013.11.027
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.83-91
  • Atatürk Üniversitesi Adresli: Evet

Özet

Brominations of mono addition products of 1,4-cyclohexadiene with 2,4-dinitrobenzenesulfenyl chloride (RSCI) selectively gave 1R(S),2R(S),4R(S),5R(S)-4,5-dibromo-2-(2,4-dinitrophenylthio)cyclohexyl acetate and 1R(S),2R(S),4R(S),5R(S)-4,5-dibromo-2-chlorocyclohexyl)(2,4-dinitrophenylthio)sulfane. From series reactions 7-oxabicyclo[4.1.0]hept-3-ene with reagents, such as RSCl, NaN3, and H2SO4/Ac2O, six 1,2,4,5-tetrasubstituted cyclohexane derivatives including S, O, N, Cl, and Br were selectively obtained. Formations and structures of the products were discussed. (C) 2013 Elsevier Ltd. All rights reserved.