Base mediated aromatization of carbonyl condensation products derived from 2-(2-bromoprop-2-enyl)cyclohexanone derivatives via 'intramolecular unsaturation transfer'

Yazicioglu E. Y., Akhmedov I. M., TANYELİ C.

HELVETICA CHIMICA ACTA, cilt.91, sa.6, ss.1148-1155, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 91 Sayı: 6
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1002/hlca.200890124
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1148-1155
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Alkylbenzenes are synthesized for the first time from aliphatic hydrocarbons via an one pot, transition metal-free coupling approach under basic conditions. The method consists of two steps: condensation of 2-bromoprop-2-enyl- or 2-propargylcyclohexanone with alcohols, amines, or amino alcohols, followed by base treatment (Scheme 1). Phenolic ethers and N-phenylated polyalkyl aromatic compounds are shown to be in the scope of the demonstrated reaction (Table). The proposed mechanism suggests that the unsaturation in another part of the molecule (propargyl-group equivalent) is transferred into the cyclohexane ring to yield a benzene ring through a series of prototropic shifts.