Issue 0, 1983

Synthesis of meta,meta-bridged biaryls ([7.0]-metacyclophanes)via aryl-aryl coupling: factors affecting the cyclisation

Abstract

Two bis(iodoaryl)heptanoids (28) and (33), the iodoarylbutyl iodoarylpropyl sulphide (39), and the corresponding sulphone (40) have been prepared, and each treated with tetrakis(triphenylphosphine)nickel(0). Two new m,m-bridged biaryls (29)(31%) and (34)(49%) were obtained; the sulphur compounds were deiodinated in preference to coupling. These reactions are compared with those used previously in myricanol synthesis and the factors affecting ring closure are discussed. Steric effects at the coupling sites appear more important in determining product yield than torsional strain in the products.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 2577-2582

Synthesis of meta,meta-bridged biaryls ([7.0]-metacyclophanes)via aryl-aryl coupling: factors affecting the cyclisation

S. E. N. Mohamed and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1983, 2577 DOI: 10.1039/P19830002577

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