Syntheses of Dihydropyrenes with Functionality in the Cavity of the ?-Electron Cloud

Article abstract of DOI:10.1021/jo01302a002

The cyano group is shown to be a good group for directing ortho lithiation and, with 2,6-dicyanotoluene as starting material, ortho lithiation provides easy access to a variety of 1,2,3-trisubstituted benzene derivatives.The use of such derivatives in the standard thiacyclophane synthesis of dihydropyrenes has provided in good yield trans-15-(4'-butenyl)-16-methyldihydropyrene (14a) and trans-15-(methoxyethyl)-16-methyldihydropyrene (14b), the first examples of dihydropyrenes having functionality within the cavity of the aromatic ?-electron cloud.