Perhalogenierte 1,2,3,5‐Dithiadiazolium‐Salze und 1,2,3,5‐Dithiadiazole

Höfs, Hans-Ulrich; Bats, Jan W.; Gleiter, Rolf; Hartmann, G.; Mews, Rüdiger; Eckert‐Maksić, Mirjana; Oberhammer, Heinz; Sheldrick, George M.

doi:10.1002/cber.19851180930

Cited by 87 publications

(50 citation statements)

References 45 publications

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“…This essentially co-planar twisted conformation 11 is observed in the methyl, trifluoromethyl, and dimethyl-amino derivatives of this radical family. Theoretical studies have been used to show that the conformation of the dimer can be changed from 10 to 11 to 12 with only small changes in the total energy of the system (24). It has been suggested that the actual orientation of the dimer may be primarily a result of simple packing forces (20).…”

Section: The General Cycloaddition Reaction Of Nitrile Sulphides Withmentioning

confidence: 99%

The preparation of 1,2,3,5-dithiadiazolium chlorides from the reaction of nitrile sulphides with thiazyl chloride

Bridson¹,

Copp²,

Schriver³

et al. 1994

Can. J. Chem.

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. Adamantyl-1,3,4-oxathiazol-2-one has been prepared for the first time and from it 1-adamantyl nitrile sulphide has been generated. Characterisation data are presented, including the X-Ray crystal structure of the oxathiazolone. (Crystal data for C,,H,,NO,S: monoclinic, space group F'2,/c, a = 11.334(2) A, b = 7.344(1) A, c = 14.373(2) A, P = 107.74(1)", V = 1139.5(3) AS, Z = 4, R = 0.042). The planar heterocyclic ring is similar to structures observed in the gas phase for other oxathiazolone derivatives. The nitrile sulphide was reacted with dimethyl-acetylene dicarboxylate in situ to give an isothiazole derivative. On a prtparC l'adamantyl-l,3,4-oxathiazol-2-one pour la premikre fois et on l'a utilise pour gCnCrer la sulfure de l-adamantyl nitrile. On prCsente les donntes ayant semi ?i sa caractCrisation, y compris la structure de l'oxathiazolone determinee par diffraction des rayons X. Les donntes cristallines pour C,,H,,NO,S sont les suivantes: cristaux monocliniques, groupe d'espace [Traduit par la Rtdaction]

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Section: The General Cycloaddition Reaction Of Nitrile Sulphides Withmentioning

confidence: 99%

The preparation of 1,2,3,5-dithiadiazolium chlorides from the reaction of nitrile sulphides with thiazyl chloride

Bridson¹,

Copp²,

Schriver³

et al. 1994

Can. J. Chem.

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“…One dimethylamino substituent was sufficient to buckle the dithiatetrazocine ring [52]. The planar structure has been found in other 8-membered rings, as the trithiatetrazocinium cation 92 [54], and the puckered boatlike ring was also found in related rings, as the 3-substituted trithiatetrazocines 93 [55]. …”

Section: Scheme 22mentioning

confidence: 99%

“…The stable heterocyclic radical 1,2,5-thiadiazolo-1,3,2-dithiazolopyrazinyl 55 was prepared by treatment of 5,6-dithiolo-1,2,5-thiadiazolo [3,4-b]pyrazine (54) with trithiazyl trichloride, S 3 N 3 Cl 3 , and purified by fractional sublimation in vacuum [38]. This method has not yet been used for other 1,3,2-dithiazoles.…”

Section: Scheme 15mentioning

confidence: 99%

Poly-sulfur-nitrogen heterocycles via sulfur chlorides and nitrogen reagents

Torroba

1999

J. prakt. Chem.

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Nitrogen and sulfur organic aromatic heterocycles are formally derived from aromatic carbon cycles by a heteroatom taking the place of a ring carbon atom or a complete CH=CH group. The presence of heteroatoms results in significant changes in the cyclic molecular structure due to the availability of unshared pairs of electrons and the difference in electronegativity between heteroatoms and carbon. Therefore, nitrogen and sulfur heterocyclic compounds display physicochemical characteristics and reactivity far from the parent aromatic hydrocarbons. On the other hand, the presence of many nitrogen and sulfur atoms in a ring is normally associated with instability and difficulties in the synthesis but, in fact, surprisingly stable heterocycles with unusual properties can be frequently obtained from simple or- Poly-Sulfur-Nitrogen Heterocycles via Sulfur Chlorides and Nitrogen ReagentsTomás Torroba* Burgos/Spain, Departamento de Química, Facultad de Ciencias, Universidad Received October 28th, 1998, respectively January 4th, 1999Keywords: Conducting materials, Nitrogen heterocycles, Phosphorus heterocycles, Selenium, Sulfur heterocycles Abstract: The family of poly-sulfur-nitrogen heterocycles includes highly stable aromatic compounds that display physicochemical properties with relevance in the design of new materials, especially those relating to molecular conductors and magnets. The interesting characteristics found in many of these heterocycles have led to the development of modern synthetic methods that are the subject of this review. Heterocycles such as 1,2,3-and 1,2,5-thiadiazoles, 1,2,3-and 1,3,2-dithiazoles, 1,2,3,5-dithiadiazoles, thiatriazines, trithiadiganic substrates and the appropriate inorganic reagent. This paper reviews the most common synthetic methods to obtain poly-sulfur-nitrogen heterocyclic systems that lie in the middle way between organic and inorganic chemistry. Carbon atoms confer high stability to such rings, according to the aromaticity and antiaromaticity rules, and the nitrogen-sulfur core gives unusual properties to the compounds, in accordance with their electron rich π-excessive nature. The physicochemical properties of this family of compounds have relevance in the design of new materials, specially concerning organic conductors. In contrast with the number and variety of such heterocycles, the number of synthetic methods to afford them is, in practice, restricted to the availability of the appropriate sulfur reagent. The classification of synthetic methods follows the applications of the most common sulfur reagents to the synthesis of heteroaromatic carbon-nitrogen-sulfur rings and sometimes extends to selenium or phosphorus related heterocycles. Binary inorganic sulfur-nitrogen cycles are covered by some reports from Chivers and Oakley [1]. Some binary S-N rings, as B-F in figure 1, constitute the models and sometimes precursors of the organic members of the series.azines, dithia(and trithia)diazepines, trithiatriazepines, dithia(and trithia)tetrazozines, and fused systems are mo...

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“…Other routes have been reported but tend to be substrate-specific (for example Mews has developed routes to the 4-halogeno-1,2,3,5-dithiadiazolium cations starting from N,Nbis(trimethylsilyl)carbodiimide). 88 Reduction of the dithiadiazolium cations 36 to the radicals 35 can be carried out with metals (sodium, 89 zinc, mercury, potassium, zinc/copper couple 90 ) organic/organometallic reagents (tetramethyl-p-phenylenediamine, triphenylverdazyl, 89 triphenylantimony 91,92 ), or reducing anions (SCN − , I − , Grignard reagents, CN − , N 3 − ). 90 The electronic structure of 1,2,3,5-dithiadiazolyl radicals 35 has been thoroughly probed.…”

Section: 235-dithiadiazolyl Radicalsmentioning

confidence: 99%

The Synthesis and Characterization of Stable Radicals Containing the Thiazyl (SN) Fragment and Their Use as Building Blocks for Advanced Functional Materials

Hicks

2010

Stable Radicals

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Perhalogenierte 1,2,3,5‐Dithiadiazolium‐Salze und 1,2,3,5‐Dithiadiazole

Cited by 87 publications

References 45 publications

The preparation of 1,2,3,5-dithiadiazolium chlorides from the reaction of nitrile sulphides with thiazyl chloride

The preparation of 1,2,3,5-dithiadiazolium chlorides from the reaction of nitrile sulphides with thiazyl chloride

Poly-sulfur-nitrogen heterocycles via sulfur chlorides and nitrogen reagents

The Synthesis and Characterization of Stable Radicals Containing the Thiazyl (SN) Fragment and Their Use as Building Blocks for Advanced Functional Materials

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