Journal of Organic Chemistry 2002-07-26

Synthesis of [n]- and [n.n]cyclophanes by using Suzuki-Miyaura coupling.

Beverly B Smith, Darron E Hill, T Ashton Cropp, Rosa D Walsh, David Cartrette, Sherry Hipps, Amy M Shachter, William T Pennington, William R Kwochka

Index: J. Org. Chem. 67(15) , 5333-7, (2002)

Full Text: HTML

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.

Related Compounds

  • 1,3-Dibromobenzene

Related Articles:

Hepatotoxicity of brominated benzenes: relationship between chemical structure and hepatotoxic effects in acute intoxication of mice.

1998-01-01

[Arch. Toxicol. 72(2) , 97-103, (1998)]

Comparison of hepatotoxicity of 1,2-, 1,3- and 1,4-dibromobenzenes: the dynamics of changes of selected parameters of liver necrosis in acute poisoning in mice.

1996-01-01

[J. Appl. Toxicol. 16(1) , 35-41, (1996)]

Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls. Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls. Basu B, et al.

[Tetrahedron Lett. 44(19) , 3817-20, (2003)]

Biochemical alterations as measures of acute and subacute hepatotoxicity of 1,3-dibromobenzene in rat.

1996-01-01

[Arch. Toxicol. 71(1-2) , 99-106, (1996)]

The disposition and metabolism of 1,3-dibromobenzene in the rat.

1999-12-01

[Chemosphere 39(13) , 2229-38, (1999)]

More Articles...