Orthocyclophanes. 1. Synthesis and characterization of [14]-and [15] orthocyclophanes and bicyclic biscyclophanes

WY Lee, CH Park, YD Kim

Index: Lee, Woo Young; Park, Chang Hee; Kim, Young Dong Journal of Organic Chemistry, 1992 , vol. 57, # 15 p. 4074 - 4079

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Citation Number: 33

Abstract

Oxidation of the diols with PCC to the corresponding cyclic diketones 23 and 29, followed by palladium-catalyzed reduction, afforded [14]-and [15] orthocyclophanes, 4 and 5. Bicyclic biscyclophanes were also prepared from the cyclic diketones giving rise to a new family of cyclophanes. Treatment of 23 and 29, respectively, with McMurry or Clemmensen reagents gave rise to intramolecular olefination to provide bicyclic biscyclophanes 24 and 30. Pd- ...