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

Date

2008-01-01

Author

Yazicioglu, Emre Y.
Akhmedov, Idris M.
Tanyeli, Cihangir

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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.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis

URI

https://hdl.handle.net/11511/38860

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.200890124

Collections

Department of Chemistry, Article

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Citation Formats

E. Y. Yazicioglu, I. M. Akhmedov, and C. Tanyeli, “Base mediated aromatization of carbonyl condensation products derived from 2-(2-bromoprop-2-enyl)cyclohexanone derivatives via ‘intramolecular unsaturation transfer’,” HELVETICA CHIMICA ACTA, pp. 1148–1155, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38860.