[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

Laura G Sarbu; Lucian G Bahrin; Peter G Jones; Lucian M Birsa; Henning Hopf

doi:10.3762/bjoc.11.207

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

Beilstein J Org Chem. 2015 Oct 15:11:1917-21. doi: 10.3762/bjoc.11.207. eCollection 2015.

Authors

Laura G Sarbu¹, Lucian G Bahrin¹, Peter G Jones², Lucian M Birsa¹, Henning Hopf³

Affiliations

¹ Department of Chemistry, "Al. I. Cuza" University of Iasi, 11 Carol I Bv., RO-700506 Iasi, Romania ; Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
² Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig.
³ Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.

Abstract

The synthesis of [2.2]paracyclophane derivatives containing tetrathiafulvalene units has been accomplished by the coupling reaction of 4-([2.2]paracyclophan-4-yl)-1,3-dithiol-2-thione in the presence of trimethylphosphite. The 1,3-dithiol-2-thione derivative was in turn synthesized by the regioselective bromination of 4-acetyl[2.2]paracyclophane, then through the corresponding dithiocarbamates and 1,3-dithiolium salts.

Keywords: 1,3-dithiolium salts; [2.2]paracyclophane; dithiocarbamates; regioselective bromination; stereoisomers; tetrathiafulvalenes.