Tandem Friedel-Crafts annulation to novel perylene analogues.
Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.
Penick
Mark A
MA
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249, USA.
Mahindaratne
Mathew P D
MP
Gutierrez
Robert D
RD
Smith
Terrill D
TD
Tiekink
Edward R T
ER
Negrete
George R
GR
D000478:Alkylation; D009284:Naphthols / Q000737:chemistry; D010084:Oxidation-Reduction; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013764:Tetrahydronaphthalenes / Q000737:chemistry
D009284:Naphthols; D013764:Tetrahydronaphthalenes; D010569:Perylene