- Unexpected production of 2,4,6-triphenyl-1,3,5-triazine in the electroreduction of 3,4-diphenyl-1,2,5-thiadiazole 1-oxide. Theoretical estimation of reactive sites for 1-oxide and 1,1-dioxide 1,2,5-thiadiazoles
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3,4-Diphenyl-1,2,5-thiadiazole 1-oxide (1a) in acetonitrile solution is electroreduced to 2,4,6-triphenyl-1,3,5-triazine and 3,4-diphenyl-1,2,5- thiadiazole. This behavior is very different from that of similar compounds with other oxidation states of the
- Aimone, Silvia L.,Mirífico, María V.,Caram, José A.,Mitnik, Daniel Glossman,Piro, Oscar E.,Castellano, Eduardo E.,Vasini, Enrique J.
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- 1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties
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A new general procedure for the selective synthesis of 1,2,5-thiadiazole 2-oxides (including fused derivatives) 8a,b,c,g,h from the reaction of vic-glyoximes with S2Cl2 and pyridine in acetonitrile was elaborated together with general procedure for the synthesis of 1,2,5-thiadiazoles 7a-i, 10, 12, and 14 from the same starting materials and reagents. Molecular structures of 3,4-dimethyl-1,2,5-thiadiazole 2-oxide 8a and [1,2,5]thiadiazolo[3,4-b]quinoxaline 10 were confirmed by single-crystal X-ray diffraction. Electrochemical properties of 1,2,5-thiadiazole 2-oxides 8 were studied by cyclic voltammetry and different behavior was observed for monocyclic and benzo-fused derivatives. With compounds 8g and 17, previously unknown deoxygenation of 2,1,3-benzothiadiazole 1-oxides was discovered by electrochemical reduction, and resulted 2,1,3-benzothiadiazoles 7g and 19 were detected in the forms of their radical anions by EPR spectroscopy combined with DFT calculations.
- Konstantinova, Lidia S.,Knyazeva, Ekaterina A.,Obruchnikova, Natalia V.,Vasilieva, Nadezhda V.,Irtegova, Irina G.,Nelyubina, Yulia V.,Bagryanskaya, Irina Yu.,Shundrin, Leonid A.,Sosnovskaya, Zhanna Yu.,Zibarev, Andrey V.,Rakitin, Oleg A.
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p. 5558 - 5568
(2015/03/30)
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- Reaction of trithiazyl trichloride with alkenes and alkynes
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Alkenes and alkynes react readily with trithiazyl trichloride 1 to give 1,2,5-thiadiazoles 2 in one step. Thus 3-amino-1,2,5-thiadiazole 5 is now readily available from N-vinylphthalimide and 1 in two steps. Cyclic alkenes react similarly to give fused thiadiazoles (7, 12) and phenanthrene gives the phenanthrothiadiazole 16. Tetra-substituted alkenes such as 13 appear to give the analogous 3,4-dihydrothiadiazoles (e.g. 14) which spontaneously ring open to give readily hydrolysed bis(methyleneamino) sulfides (e.g. 15). A simple set of mechanisms is proposed for all of these reactions.
- Duan, Xiao-Guang,Duan, Xiao-Lan,Rees, Charles W.,Yue, Tai-Yuen
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p. 2597 - 2601
(2007/10/03)
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- Organic Heterocyclothiazenes. Part 2. Reaction of Tetrasulphur Tetranitride with Phenylacetylene and Diphenylacetylene
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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
- Daley, Stephen T. A. K.,Rees, Charles W.
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p. 207 - 210
(2007/10/02)
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- A-ALKYLATION, ALKENYLATION, AND ARYLATION OF 1,2,5-THIADIAZOLES
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A new synthetic method of 1,2,5-thiadiazoles is reported, which affording mono- or disubstituted derivatives by one pot procedure, clarifies unknown aspects of the 1,2,5-thiadiazole ring reactivity.
- Munno, Angela De,Bertini, Vincenzo,Picci, Nevio
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p. 1131 - 1136
(2007/10/02)
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- Reactions of Tetrasulphur Tetranitride with Alkynes; 1,4,2,6-Dithiadiazines and 1,3,2-Dithiazoles
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Reaction of S4N4 with diphenylacetylene and phenylacetylene gives two new, thermally stable heterocyclic systems, the 1,4,2,6-dithiadiazine (3) and the 1,3,2-dithiazolylimine (7), respectively, as minor products; these structures, determined by X-ray diff
- Daley, Stephen T. A. K.,Rees, Charles W.,Williams, David J.
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- SULFUR NITRIDE IN ORGANIC CHEMISTRY. 12. THE REACTION OF N4S4 WITH 1-ARYL-1-TRIMETHYLSILYLOXYETHYLENES AFFORDING 3-HYDROXY-4-ARYL-1,2,5-THIADIAZOLES
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Reaction of N4S4 with 1-aryl-1-trimethylsilyloxyethylenes (1a-1e) gave 3-hydroxy-4-aryl-1,2,5-thiadiazoles (2a-2e) though the yields were low. 3-Amino-4-thienyl-1,2,5-thiadiazole (3) was obtained as a minor product.
- Mataka, Shuntaro,Takahashi, Kazufumi,Tashiro, Masashi
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p. 2047 - 2050
(2007/10/02)
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- REACTION OF BENZILMONOHYDRAZONE WITH S4N4, A CORRECTION
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Reaction of benzilmonohydrazone (1) with S4N4 gives the azine (6) and not the 2-H-imidazole (2); this invalidates the claim that (2) is not the intermediate in the formation of N-benzoyltriphenylimidazole from benzil and ammonia.S4N4 converts diphenylketene into thiobenzophenone.
- Daley, Stephen T. A. K.,Rees, Charles W.
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p. 1759 - 1760
(2007/10/02)
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- Sulfur Nitride in Organic Chemistry. 9. The Reaction of Tetrasulfur Tetranitride with Benzyl Ketones. Preparation of 3,4-Disubstituted-1,2,5-thiadiazoles
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The reaction of tetrasulfur tetranitride (1) with various aryl and benzyl ketones (2a-o), oxindole (11), benzyl α-pyridyl ketone (12) and α-phenacylpyridine (13) afforded the corresponding 1,2,5-thiadiazoles (3a-n, 11 and 14).The scope and limitations of the above reaction were investigated and the evidences suggesting the radical anion mechanism are presented.
- Mataka, Shuntaro,Hosoki, Akira,Takahashi, Kazufumi,Tashiro, Masashi
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p. 1681 - 1685
(2007/10/02)
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