Synthesis of sym-(E/Z)-Diselenadithiafulvalene

Article abstract of DOI:10.1021/jo01301a018

sym-Diselenadithiafulvalene (3) has been synthesized as an inseparable E,Z isomer mixture by two fundamentally different routes.The first synthesis proceeds via ethylene diselenocyanate (9), ethane-1,2-diselenol (8), 1,3-Diselenolane-2-thione (7), 4,5-bis(carbomethoxy)-1,3-thiaselenole-2-selone (12),and tetrakis(carbomethoxy)-sym-diselenadithiafulvalene (13).The second synthesis,which involves a greatly improved route to 1,3-thiaselenole-2-selone (18),provides the most practical method available for the preparation of larger quantities of 3.