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 dithiacyclophanes have been examined as a potential route to chiral biaryl dithiols. Reaction of the resolvable dibromide 2,2'-bis(bromomethyl)-1,1'-binaphthalene with 1,1'-binaphthalene-2,2'-dithiol gave a diastereoisomeric mixture of dithiacyclophanes. Reaction of 1,1'-binaphthalene-2,2-'bis(methylenethiol) with 2,2'-bis(bromomethyl)-1,1'-binaphthalene gave a mixture including dinaphtho[2,1-c:1',2'-d]thiepin and the racemic diastereoisomer of 11,13,26,28-tetrahydrotetranaphtho[2,1-c:1',2'-e:2'',1''-j:1''',2'''-l][1,8]dithiacyclotetradecin.