[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

• Laura G. Sarbu,
• Lucian G. Bahrin,
• Peter G. Jones,
• Lucian M. Birsa and
• Henning Hopf

Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

• -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: dithiocarbamates; 1,3

• field (ca. 180 ppm) which corresponds to the electron-deficient C-2 atom. 1,3-Dithiolium salts are valuable precursors for tetrathiafulvalenes. There are two main synthetic approaches that are mainly based on the exploitation of the electron-deficient character of the C-2 carbon atom. One of these

• involves the conversion of 2-N,N-dialkylamino-1,3-dithiolium salts into the corresponding 2-unsubstituted 1,3-dithiolium salts, followed by the homocoupling of the carbene intermediate that is generated under basic conditions. Unfortunately, our attempts to synthesize the 2-unsubstituted derivative from

Tricyclic flavonoids with 1,3-dithiolium substructure

• Lucian G. Bahrin,
• Peter G. Jones and
• Henning Hopf

Beilstein J. Org. Chem. 2012, 8, 1999–2003, doi:10.3762/bjoc.8.226

• survey revealed that a P2O5/CH3SO3H (1:10, m/v) mixture may be the cyclization agent of choice to obtain 1,3-dithiolium salts 7g and 7h as pure compounds and in high yields [28][29]. Thus, a suspension of 6g or 6h in three parts of the ‘‘superacid’’ mixture was stirred at room temperature for 30 min to