J. Meinwald, D. Dauplaise, J. Clardy
Nov 1, 1977
Citations
1
Influential Citations
36
Citations
Journal
Journal of the American Chemical Society
Abstract
The synthesis of unsymmetrical naphthol(1,8-cd)1,2-selenathile (IV), naphthol(1,8-cd)-1,2-tellurathiole (V), and naphthol(1,8-cd)-1,2-telluraselenole (VI) from 1,8-dibromonaphthalene is reported. The methodology is illustrated by the preparation of (IV) in which (VII) reacts sequentially with 1 equiv of n-butyllithium, i equiv of elemental S, a 2n equiv of n-butyllithium, and 1 equiv of elemental Se. (IV) is a dark red solid and its crystal structure was determined. (V) is obtained as bronze filaments and (VI) as shiny black flakes. These unsymmetrically bridged naphthalenes are good electron donors and form charge-transfer complexes with both 7,7,8,8-tetracyanoquinodimethane and iodine. (JSR)