Journal of the American Chemical Society

The condensation of camphene and phenol. Product formation via a direct 2, 6-hydride transfer

WF Erman

Index: Erman,W.F. Journal of the American Chemical Society, 1964 ,  vol. 86, p. 2887 - 2897            

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Citation Number: 19

Abstract

Reaction of &-camphene and phenol at 0'with catalytic quantities of boron trifluoride etherate yielded isobornyl phenyl ether (1) in SOTo yield. In contrast, treatment of camphene and phenol with boron trifluoride etherate under C-alkylation conditions (100') afforded not only the 0-and p-isobornylphenols (2 and 3) but also the o-and p-6-exo-hydroxyphenyl-exo- isocamphanes (4 and 5). Product formation was stereospecific as evidenced by absence ...