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.
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