SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF DITHIACYCLOPHANES DERIVED FROM BIARYLDITHIOLS

The relative efficiencies of the reaction of dibromides with biphenyl- 2,2'-dithiol and 1,1'-binaphthalene-2,2'-dithiol to produce dithiacycl ophanes have been examined as a potential route to chiral biaryl dithi ols. Reaction of the resolvable dibromide 2,2'-bis(bromomethyl)-1,1'-b inaphthalene with 1,1'-binaphthalene-2,2'-dithiol gave a diastereoisom eric mixture of dithiacyclophanes. Reaction of 1,1'-binaphthalene-2,2- 'bis(methylenethiol) with 2,2'-bis(bromomethyl)-1,1'-binaphthalene gav e a mixture including dinaphtho[2,1-c:1',2'-d]thiepin and the racemic diastereoisomer of :2'',1''-j:1''',2'''-l][1,8]dithiacyclotetradecin.