Synthesis of Tetrathiafulvalene Derivatives with Bromo m-xylyl and Acetulated Glucose Units: Precursors to Tetrathiafulvalene Macrocycles

Two tetrathiafulvalene derivatives: tetrathiafulvalene with two bromo m -xylyl substituents ( 1 ) and tetrathiafulvalene with two acetylated bromo-glucopyranosyl substituents ( 2 ) were synthesized. The synthesis involved the preparation of the cyanoethyl protected tetrathiafulvalene ( 10 ) from zinc complex ( 6 ) in five steps. Deprotection of ( 10 ) using cesium hydroxide and the reaction of the resulting dithiolate with 2.5 equivalent of α, α' m -xylyldibromide yielded 8.408% of ( 1 ), while the addition of 1-bromo-2,3,4-tri-O-acetyl-6- iodoglucopyranoside ( 13 ) to deprotected ( 10 ) produced ( 2 ) in 16.19% yield. The TTF derivatives ( 1 ) and ( 2 ) could be used as precursors to the synthesis of macrocycles containing phenyl and/or sugar units.