5‐Chloro‐3‐methylthio‐1,2,4‐thiadiazol‐2‐ium chlorides as useful synthetic precursors to a variety of 6aλ<sup>4</sup>‐thiapentalene systems

Morel, G.; Marchand, Evelyne; Sinbandhit, Sourisak; Toupet, Loı̈c

doi:10.1002/hc.10106

Cited by 15 publications

(3 citation statements)

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“…After dichloromethane extraction of the organic phase followed by removal of the solvent 1 or 2 was isolated by distillation in vacuo by using a Kugelrohr apparatus at 50 8C or 70 8C, respectively, which was a small modification to the literature preparation of 1 and 2 in water followed by steam distillation, [31] though only melting point and IR spectroscopy were mentioned in this report. More recently the 13 C NMR of 1 was reported by Morel et al [27] Compound 1 is a pale yellow oil which upon cooling slightly became a pale yellow crystalline solid. Compound 2 is a yellow oil.…”

Section: Resultsmentioning

confidence: 93%

“…Morel et al [27] d = 173.2 (C5) and 172 ppm (C3)). Our assignment was confirmed by H-C HMBC and H-C HSQC experiments.…”

Section: C{mentioning

confidence: 95%

“…[27] We also report the synthesis of model compounds composed of two 1,2,4-thiadiazole rings linked by a sulfur bridge. Selected examples have been studied by X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

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Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)_x

Bowman

Burchell

Kilián

et al. 2006

Chemistry A European J

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The synthesis and full characterisation of a series of 1,2,4-thiadiazoles is reported. (SCN)(x) has been studied by a variety of techniques and the data compared with 1,2,4-thiadiazole and 1,2,4-dithiazoles. The observed data suggest that the polymer consists of 1,2,4-dithiazole rings linked by nitrogen atoms. For (SCN)(x), the MALDI-TOF mass spectroscopy showed a parent ion at 1149 and a series of peaks with (SCN)(2) repeat units (116 m/z); this result implies that (SCN)(2) may be the monomer unit of the polymer. Its IR spectrum shows a very broad peak with maximum at 1134 cm(-1) consisting of several overlapping peaks in the same region as ring vibrations for 1,2,4-thiadiazole and 1,2,4-dithiazole compounds. Peaks in the Raman spectrum in the range 400-480 cm(-1) support the presence of disulfide units within the polymer. The solid-state (13)C NMR (99 % (13)C-labelled) spectrum is dominated by two singlets of equal intensity at approximately 187 and 184 ppm with low intensity peaks in the range 152-172 ppm, in approximately the same range as both 1,2,4-thiadiazoles and 1,2,4-dithiazoles. The solid-state (15)N NMR (99 % (15)N labelled) spectrum displays two major peaks of similar intensity at 236.9 and 197.2 ppm, which are clearly very different environments to those observed in bis(3-bromo-1,2,4-thiadiazol-5-yl) disulfide, but similar to 1,2,4-dithiazoles. The X-ray structures of seven C-S-N systems are reported. Preliminary studies on (SeCN)(x) suggest that literature references to this polymer may be in error with the red solid actually being red selenium.

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Section: Resultsmentioning

confidence: 93%

“…Morel et al [27] d = 173.2 (C5) and 172 ppm (C3)). Our assignment was confirmed by H-C HMBC and H-C HSQC experiments.…”

Section: C{mentioning

confidence: 95%

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Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)_x

Bowman

Burchell

Kilián

et al. 2006

Chemistry A European J

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Recent Advances of Structural Chemistry of Organoselenium and Organotellurium Compounds

Nakanishi

Hayashi

Hashimoto

et al. 2014

Patai's Chemistry of Functional Groups

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The recent advances of structural chemistry of organoselenium and organotellurium compounds are reviewed. The basic concepts of structural chemistry of the compounds are well summarized in Chapter 3 of Volume 1 in this series. About 9,000 structures for the compounds have been reported since then, therefore only selected results can be discussed here. Such compounds are expected to contain at least one CE (E = Se or Te) bond, although those with no CE bonds are also discussed, as necessary. Compounds containing CE (E = Se and Te) are discussed in some detail. Structures of unstable and/or reactive species are explained in detail, which are stabilized by the formation of dimers or higher oligomers or using large protecting groups. Bis‐selenides and bis‐tellurides and the derivatives at the naphthalene 1,8‐positions and the related systems are discussed in detail. The compounds containing hypervalent interactions are also discussed in detail. The idea is applied to the intramolecular and intermolecular linear interactions in crystals. In this connection, the extended hypervalent interactions are also explained in detail for the linear interactions longer than three, exemplified by typical cases and unique cases in crystals.

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Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactive ψ‐Dinitroso Substituents

et al. 2005

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[1][2][3][4] tetraazaphosphapentalenes (TAPP), [5] tetraazathiapentalenes (TATP), [6][7] tetraazaselenapentalenes (TASP), [8][9] and their derivatives (Scheme 1) are of special interest owing to their unusual electronic structure and chemical behavior which is governed by the striking orientations of the heteroatoms. These heterocyclic systems promise a variety of applications including in organic synthesis, redox chemistry, and in industry, military, and space programs. Some examples of these applications include the derivatization of p-hypervalent heterocyclic TATP, [10][11][12] the synthesis of versatile heterocyclic compounds, [13][14][15] exotic metal carbene chemistry, [16][17][18][19][20] shaped charges for downhole penetrators, [21] and thermally stable high-energy materials. [22][23][24][25][26] Much attention has been focused on the preparation (precursors and methods) and properties of the heterocyclic tetraazapentalenes and their derivatives because their applications depend significantly on their thermal stability, performance, and synthetic practicality.We are interested in the preparation of high-nitrogencontent energetic materials, heterocyclic high-density materials, and green primary explosives for a wide variety of applications through the utilization of tetrazines, [27] tetrazoles, [28] triazines, [29] furazans, [30] triazoles, [31] pyridines, [32] and azetidines.[33] Our interest in heterocyclic tetraazapentalenes was to probe the explosive performance (detonation velocity (V D ) and detonation pressure (P CJ )) of previously synthesized, thermally stable high-energy compounds and to Scheme 1. The structures of tetraazapentalenes (TAPs), tetraazaphosphapentalenes (TAPPs), tetraazathiapentalenes (TATPs), and tetraazaselenapentalenes(TASPs).

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5‐Chloro‐3‐methylthio‐1,2,4‐thiadiazol‐2‐ium chlorides as useful synthetic precursors to a variety of 6aλ⁴‐thiapentalene systems

Cited by 15 publications

References 33 publications

Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)_x

Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)_x

Recent Advances of Structural Chemistry of Organoselenium and Organotellurium Compounds

Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactive ψ‐Dinitroso Substituents

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5‐Chloro‐3‐methylthio‐1,2,4‐thiadiazol‐2‐ium chlorides as useful synthetic precursors to a variety of 6aλ4‐thiapentalene systems

Cited by 15 publications

References 33 publications

Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)x

Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)x

Recent Advances of Structural Chemistry of Organoselenium and Organotellurium Compounds

Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactive ψ‐Dinitroso Substituents

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5‐Chloro‐3‐methylthio‐1,2,4‐thiadiazol‐2‐ium chlorides as useful synthetic precursors to a variety of 6aλ⁴‐thiapentalene systems

Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)_x

Investigations on Organo–Sulfur–Nitrogen Rings and the Thiocyanogen Polymer, (SCN)_x