K W Hipps - Synthesis of [n]- and [n.n]Cyclophanes by Using Suzuki−Miyaura Coupling

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  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