Chemistry of .alpha.,.beta.-unsaturated thione dimers. 3. Reactions of thiochalcones and 2-arylidene-1-thiotetralones with cumulenes containing a carbon-carbon double bond
Though the reaction of chalcones 2 with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide 1 in refluxing benzene gave the corresponding thiochalcone dimers 3, the reaction in refluxing xylene gave new phosphorus-containing compounds, 2-(4-methoxyphenyl)-3,5-diaryl-Δ4-1,2-thiaphospholene-2-sulfides 4.
ene-1-thione (thiochalcone) reacted with diphenylcydopropenone across the =C–CO bond giving a thiophene derivative and a polysubstituted phenol with the arylketene/sulfur elimination, whereas the reaction with diphenylcydopropenethione took place at the C=S bond affording a spiro compound.
Phosphorin 1-sulfides generated by the thermolysis of 1-phospha-2-thiabicyclo[4.4.0]deca-3,7,9-triene 1-sulfides reacted with triphenylphosphine, dienophiles, or nucleophiles to give the corresponding phosphorins, 1-phosphabicyclo[2.2.0]octa-2,5-diene 1-sulfide, or 1,2-dihydrophosphorin 1-sulfide derivatives, respectively.