6579-12-0Relevant academic research and scientific papers
Organic Heterocyclothiazenes. Part 2. Reaction of Tetrasulphur Tetranitride with Phenylacetylene and Diphenylacetylene
Daley, Stephen T. A. K.,Rees, Charles W.
, p. 207 - 210 (2007/10/02)
The reaction of S4N4 with diphenylacetylene in boiling toluene has been found to give 3,4-diphenyl-1,2,5-thiadiazole (1) as the major product and 3,5-diphenyl-1,4,2,6-dithiadiazine (4), a new heterocyclic system, as a minor product.The same reaction with
HETEROCYCLIZATION OF ACETYLENE DERIVATIVES BY THE ACTION OF SULFUR DIOXIDE AND HYDROGEN BROMIDE
Zborovskii, Yu. L.,Smirnov-Zamkov, I. V.,Staninets, V. I.
, p. 1617 - 1625 (2007/10/02)
Under the influence of sulfur dioxide and hydrogen bromide acetylenes activated by strong electron-withdrawing substituents undergo oxidative-reductive heterocyclization, leading to the formation of heterocyclic systems containing sulfide sulfur.The hydrogen bromide acts as reducing agent in these processes.The released bromine oxidizes the excess of sulfur dioxide to sulfuric acid.The reaction takes place by a heterolytic donor-acceptor mechanism.The addition of hydrogen bromide and sulfur dioxide to the CC bond evidently gives sulfinic acids, which are thenreduced to sulfenyl bromides.In the case of phenylacetylene derivatives intramolecular cyclization of the sulfenyl bromides leads to the formation of benzothiophenes.The dicyanoacetylene and acetylenedicarboxamide are converted into the corresponding isothiazoles.The heterocyclization of two molecules of sulfenyl bromide leads to the formation of 1,4-dithiin derivatives.
