Synthesis of Tetrathiafulvalene Derivatives with Bromo m-xylyl and Acetulated Glucose Units: Precursors to Tetrathiafulvalene Macrocycles
Kristine G. Eusebio | Sheryl Robles-lontok | Glenn V. Alea
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.