Reaction of the bis-9-BBN adduct of several dienes with 1,3-dibromobenzene via Suzuki coupling leads to a series of [n]metacyclophanes ranging in size from 10 to 17 atom members. In each case, two carbon-carbon bonds are formed in one reaction vessel. However, when the bis-9-BBN adduct of 1,5-hexadiene is coupled with a variety of aryl dihalides, larger [n.n]cyclophanes were formed in preference to the [n]cyclophanes. Four carbon-carbon bonds are formed in this instance. Single-crystal X-ray analyses of these [n.n]cyclophanes reveal interestingly shaped molecules with large cavities.
CyclophanesCyclophanes O 0450 Synthesis of [n]-and [n.n]Cyclophanes by Using Suzuki-Miyaura Coupling. -A number of novel cyclophanes are prepared. -(SMITH, B. B.; HILL, D. E.; CROPP, T. A.; WALSH, R. D.; CARTRETTE, D.; HIPPS, S.; SHACHTER, A. M.; PENNINGTON, W. T.; KWOCHKA*, W. R.; J. Org. Chem. 67 (2002) 15, 5333-5337; Dep. Chem., Western Carolina Univ., Cullowhee, NC 28723, USA; Eng.) -Jannicke 03-056
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