Publication Details (including relevant citation information):
Smith, Beverly B., Hill, Darron E., Cropp, T. Ashton, Walsh, Rosa D., Cartrette, David, Hipps, Sherry, Shachter, Amy M., Pennington, William T., Kwochka, William R. The Journal of Organic Chemistry 2002 67 (15) 5333-5337
Abstract: 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.
Address (URL): http://dx.doi.org/10.1021/jo025509m