Synthesis of meta,meta-bridged biaryls ([7.0]-metacyclophanes)via aryl-aryl coupling: factors affecting the cyclisation
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2577-2582
- https://doi.org/10.1039/p19830002577
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.Keywords
This publication has 0 references indexed in Scilit: