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Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘ Intramolecular Unsaturation Transfer ’
Author(s) -
Yazıcıoğlu Emre Y.,
Akhmedov İdris M.,
Tanyeli Cihangir
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890124
Subject(s) - chemistry , intramolecular force , aromatization , degree of unsaturation , ring (chemistry) , cyclohexanone , organic chemistry , base (topology) , medicinal chemistry , yield (engineering) , condensation , catalysis , mathematical analysis , materials science , physics , mathematics , metallurgy , thermodynamics
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.