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Modern Friedel-Crafts Chemistry. Part 38. Facile Synthesis of Acenaphthenes via Direct and Rearranged Intramolecular Friedel-Crafts Cyclialkylations of Intermediate Carbinols

Research Authors
Hassan Abdou Kotb Abd El-Aal and Ali A. Khalaf
Research Abstract

A novel one-pot synthesis of six di-, tri-, and tetra-substituted acenaphthenes 18a-f via
direct and/or rearranged Friedel-Crafts cyclialkylations of seven novel carbinols 1a-g
is described. The methodology involves treatment of alkanols 1a-g in the presence of
both Brønsted (PPA, H2SO4) and Lewis (AlCl3/CH3NO2) acid catalysts. The method
offers several advantages such as high yields, high selectivities, and easily accessible
starting materials. A plausible mechanism for this type of Friedel-Crafts cyclialkylation
is proposed.

Research Department
Research Journal
Polycyclic Aromatic Compounds
Research Rank
1
Research Vol
Vol.33
Research Year
2013
Research Pages
PP.331–346