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Synthesis of New Heterocycles by Halogenation of Tetrasulfur

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Synthesis of New Heterocycles by Halogenation of Tetrasulfur Synthesis of New Heterocycles by Halogenation of Tetrasulfur Tetranitride S4N4* Y. MONTEIL and H. VINCENT Universite Claude Bernard, Lyon I, Laboratoire de Physico-Chimie minerale, Associe au C.N.R.S. N° 116, Service du Pr. Cueilleron, 43, Bd. du 11 novembre 1918, 69621 Villeurbanne, France (Z. Naturforsch. 31 b, 673-676 [1976]: received October 7, 1975) Inorganic Heterocycles, Thiazyl Compounds, Tetrasulfur Tetranitride Reactions, P-S-N Compounds Bromine reacts with tetrasulfur tetranitride S4N4 in solution in different solvents to give thiodithiazyl dibromide S3N2Br2. Iodine reacts under the same conditions with S4N4 to give trithiazyl iodide (SN)3l. The addition of chlorine, bromine or iodine to a mixture of tetrasulfur tetranitride and white phosphorus leads to compounds with the general formula P2S3NsXw, with n — 1 or 3 depending on the nature of X. Introduction Moreover, we obtained also new combinations The thiazyl SN radical, the analogue of nitric containing the pattern P2S3N3 by reaction of oxide NO, polymerizes easily owing to the sulfur halogens on a mixture of white phosphorus with d-orbitals. The better known of these polymers, tetrasulfur tetranitride. tetrasulfur tetranitride S4N4 can give SN radicals in the course of reactions, but it is at present impos- A. Starting Compounds sible to predict how and where SN bond rupture Very pure compounds are required to study the occurs during a given reaction. reaction of the halogens with tetrasulfur tetranitride. The S4N4 structure is known1. This heterocycle We have been obliged to synthetize some thiazyl can lead to other cycles with very different shapes. chlorides which have been used either as reference Examples are the structures of the compounds or as starting materials for the bromination and 3 4 2 5 iodination reactions. S4N4F4 , S3N3CI3 , S3N2CI2 , S4N3NO3 , S5N5A1C14 e and S6N4X2 7. A.l. Tetrasulfur tetranitride S4N4 The large variety of the compounds produced Numerous authors studied the preparation of from S4N4 shows that it is a good starting material S4N4. We used the method which has been perfected for the synthesis of new combinations. by BECKE-GOEHRING and revised by VILLENA- The action of fluorine on S4N4 leads to the BLANCO and JOLLY14. In this method S4N4 is compound S4N4F48. The chlorination reaction obtained by ammonolysis of disulfur dichloride yields S3N3CI39, via the intermediate step of according to the overall reaction: S4N4CI410. We studied the bromination and the iodination of S4N4. While the bromination of S4N4 6 S2CI2 + 16 NH3 S4N4 + 12 NH4C1 + 8 S. has been studied by several workers11-13, it is the S4N4 is little sensitive to moisture. Consequently, first time that the iodination reaction is reported. it is easy to remove ammonium chloride by water treatment of the product at 0 °C. On the other hand, the separation from sulfur is much more delicate * Paper, presented at the 1. International Symposium on Inorganic Heterocycles, Besan^on (France), June because it is soluble in the same solvents as S4N4. 16-19, 1975. After several recrystallisations of the S-S4N4 mix- ture from dioxane and benzene, it is possible to Requests for reprints should be sent to Prof. Dr. Y. MONTEIL, Universite Claude Bernard Lyon I, Lab. obtain a product enriched in S4N4. This is then de Physico-Chimie Minerale I, Associe au C.N.R.S., chromatographed on a column of acid alumina to Service du Pr. Cueilleron, 43, Boulevard du II No- 15 vembre 1918, F-69621 Villeurbanne, France. exclude the residual sulfur . Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Advancement of Science under a Creative Commons Attribution Creative Commons Namensnennung 4.0 Lizenz. 4.0 International License. 674 Y. MONTEIL-H. VINCENT • SYNTHESIS OF NEW HETEROCYCLES IR (KBr pellet) absorptions occurred (cm-1) at: IR (CsBr pellet) absorptions occurred (cm-1) at: 925 s, 800 w, 768 w, 760 w, 728 s, 698 vs, 620 m, 1160 vs, 1125 m, 998 vs, 682 s, 608 m, 565 s, 465 vs, 550 vs, 528 m, 519 w. 450 s, 325 s. Powder diffraction data (copper radiation) at: Powder diffraction data (copper radiation) at: 6.33 m, 6.04 m, 4.75 vs, 4.60 vs, 4.37 m, 3.11m, 5.31 s, 4.56 m, 4.06 s, 3.21 m, 3.06 vs, 2.93 m, 2.78 s Ä. 2.71 s, 2.56 ml. A.2. Thiodithiazyl dichloride S3N2CI2 A 5. Thiotrithiazyl bromide SiN3Br Thiazyl chlorides can be prepared from tetra- The ionic character of the thiotrithiazyl chloride sulfur tetranitride9. Ammonium chloride and di- and the stability of the S4N3+ ion enables the sulfur dichloride are the preferred starting materials. bromide to be obtained by methatesis with potas- They react easily according to the scheme17: sium bromide17: 2 NH4CI + 4 S2CI2 -> S3N2CI2 + 8 HCl + 5 S. S4N3+C1- + K+Br- -> S4N3Br + K+Cl-. The reaction is carried out in presence of sulfur The reaction has been carried out either in water at to restrict the disproportionation of disulfur di- 0 °C or in formic acid. The thiotrithiazyl bromide chloride in sulfur dichloride SCI2. The compound precipitates from the solution: S3N2CI2 segregates easily from the reaction mixture IR (CsBr pellet) absorptions occurred (cm-1) at: by sublimation. Since it is easily obtained, it is used 1155 s, 992 vs, 670 m, 558 m, 462 vs, 315 s. as a starting material for the preparation of the Powder diffraction data (copper radiation) at: 5.41 s, 5.23 s, 4.79 s, 4.24 m, 4.08 s, 3.45 m, 3.17 m, thiazyl chlorides S4N3CI and S3N3CI3 instead of 3.10 vs, 2.96 m, 2.75 s, 2.64 s, 2.60 m Ä. S4N4 17. IR (nujol mull) absorptions occurred (cm-1) at: B. Study of the Bromination of S4N4 1015 m, 940 s, 582 m, 548 w, 460 w, 398 w. The first study11 on the bromination of tetra- Powder diffraction data (copper radiation) at: 4.57 vs, 4.28 m, 4.07 s, 3.73 m, 3.42 m, 3.34 m, sulfur tetranitride reported the formation of 2.70 s, 2.68 vs, 2.60 s, 2.51 m, 2.27 m Ä. (SNBr)^. More recently, HEAL12 and ZBORILOVA13 concluded that a mixture of products is formed with A.3. Trithiazyl trichloride S3N3CI3 a composition close to the formula S3N2Br2- Trithiazyl trichloride is obtained by chlorination We studied the reaction between S4N4 and of thiodithiazyl dichloride: bromine in carbon disulfide or carbon tetrachloride. 3 S3N2CI2 + Cl2 -> 2 S3N3CI3 + 3 SC12. It is very important to use moisture free conditions, i.e. strictly anhydrous solvents. Moreover, tetra- It can be separated from S3N2CI2 due to its solubility sulfur tetranitride must be free from sulfur. All in carbon tetrachloride and benzene. The compound manipulations must be carried out in an inert S3N3CI3 is very sensitive to moisture and must atmosphere and the reaction products are therefore therefore be handled in a glove-box. handled in a glove-box. The reaction between S4N4 IR (CS2 or CCI4 solution) absorption occurred and bromine has been studied at different tem- (cm-1) at: 1017 vs, 701s, 621 w, 514 s, 390 m, peratures. 260 w. Powder diffraction data (copper radiation) at: 5.56 s, 5.40 s, 4.08 s, 3.15 vs, 3.11 m, 3.06 m, 2.90 s, B.l. Preparations of SsN^Brz 2.64 vs, 1.90 m, 1.79 m, 1.61 m, 1.52 m Ä. A solution of S4N4 and bromine in CS2 is refluxed for one hour. The precipitate found is thiodithiazyl A.4. Thiotrithiazyl chloride S4N3CI dibromide. This new compound is a yellow-orange Thiotrithiazyl chloride is obtained by reaction coloured crystalline product. between thiodithiazyl dichloride and disulfur di- S2N2Br2 has been obtained also by brominating chloride : S2N2CI2 with HBr. The solid-gas phase reaction 3 S3N2CI2 + S2CI2 -> 2 S4N3CI + 3 SC12. proceeds according to the equation: The compound is ionic, S4N3+C1-, and the struc- S3N2CI2 + 2 HBr -> S3N2Br2 + 2 HCl. ture of the S4N3+ ion has been determined using a The formation of HCl is evidenced by IR ab- single crystal of thiotrithiazyl nitrate5. Further sorption spectroscopy. Yet, the product is less pure data are: than the SßNoBro obtained by bromination of S4N4. 675 Y. MONTEIL-H. VINCENT • SYNTHESIS OF NEW HETEROCYCLES Experimental B.3. Transformation of SsN%Br2 into S^NsBr A 250 ml flask was equipped a reflux condenser Thiotrithiazyl bromide S4N3Br has been found and the top of the condenser was fitted with a as an impurity in thiodithiazyl dibromide in the drying tube filled with calcium chloride. The bromination of S4N4. It can result either from the reaction temperature was controlled with an electric heating mantle. hydrolysis of S3N2Br2 or from the presence of sulfur The reaction flask was charged with 200 ml of CS2 formed in the reaction of bromine on S4N4. The or CCI4 dried with molecular sieves, and 1.84 g thermal decomposition of SsN2Br2 leads likewise to (0.01 mol) of S4N4 recrystallised in CßHe just prior the formation of S4N3Br. to use. After dissolution of S4N4, 3 ml of Br2 was SsN2Br2 is very sensible to moisture. It decom- added. The reaction mixture was allowed to reflux for two hours. Then the SsN2Br2 was collected by poses in the atmosphere giving mainly thiotri- filtration in a glove-box, desiccated with P2O5, and thiazyl bromide and ammonium bromide.
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