Journal of Organic Chemistry p. 2746 - 2749 (1980)
Update date:2022-08-04
Topics:
Mao, Yuh-lin
Boekelheide, Virgil
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.
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