The preparation by standard methods of a number of 1-aryl, 2-aryl and l,2-diarylnorbornane derivatives desired for physical organic investigations is reported (Chart I). The key step wit9 the Wagner-Meerwein rearrangement of 2-aryl-2-endonorbornanols VI1 to esters of 1-aryl-2-em-norbornanols X in acid media. The structures of the rearranged products were proven by chemical and spectroscopic means. Several incidental observations are described.Although a number of aryl substituted camphor, fenchone and camphenilone compounds have been simple aryl derivatives of bicyclo I2.2. llheptane have not been thoroughly studied. 5-Phenyl-2-norbornene1 the Diels-Alder adduct of styrene and cyclopentadiene, was the first example of this latter type r e p~r t e d .~Bruson'O investigated the hydration of this olefin, but neither the composition nor the structure of the product was established. Saunders and Benjamin1' have shown recently that the reaction gave a complex mixture of 5and 6-phenyl-2-norbornanols. 3-Phenyl-2-(1) Paper VI of a series on Bridged Ring Systems. We abandoned attempt8 to use this ioute for preparative purposes when the complexit>g of the hydration product became apparent.)
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