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American Chemical Society
A series of doubly bridged p-terphenyls (4) have been synthesized utilizing a facile three-step synthesis starting from the readily available diacetylenic precursor (1) in excellent overall yields, and their structures were confirmed by 1H/13C NMR spectroscopy as well as by X-ray crystallography. The racemization barrier between the meso and chiral atropisomers of one of the derivatives of 4 was found to be ∼12 kcal/mol by variable-temperature NMR spectroscopy. The versatility of the protocol developed herein was further demonstrated by the preparation of a quadruply bridged penta-p-phenylene derivative.
Modjewski, Matthew J.; Lindeman, Sergey V.; and Rathore, Rajendra, "A Versatile Preparation of Geländer-Type p-Terphenyls from a Readily Available Diacetylenic Precursor" (2009). Chemistry Faculty Research and Publications. 542.
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