1,2‐Dithiins, a New Type of Heterocycle

Schroth, Werner; Billig, F.; Reinhold, G.

doi:10.1002/anie.196706981

Cited by 45 publications

(10 citation statements)

References 6 publications

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“…However, geometry 13 C NMR spectra of 1,2-dithiin and its homologues suggest optimized MNDO and STO-3G ab initio calculations give that the ring structure, 1, rather than the acyclic valence a planar ground state structure for 1 (8). No gas-phase studtautomer (2 in Scheme 1) exists in solution (2)(3)(4)(5). Support ies of 1 have been reported, but recent X-ray crystallographic for the cyclic form, 1, also comes from NMR studies and analyses have shown that the 1,2-dithia-3,5-cyclohexadiene calorimetric measurements of substituted 1,2-dithiins (6,7).…”

Section: Introductionmentioning

confidence: 96%

Microwave Spectra, Molecular Structure, and Electric Dipole Moment of 1,2-Dithiin

Gillies

Cotter

et al. 1996

Journal of Molecular Spectroscopy

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Section: Introductionmentioning

confidence: 96%

Microwave Spectra, Molecular Structure, and Electric Dipole Moment of 1,2-Dithiin

Gillies

Cotter

et al. 1996

Journal of Molecular Spectroscopy

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“…The synthesis of 3,6-diphenyl-1,2-dithiin was performed according to the literature procedure. 2 Cyclic Voltammetry. Conventional cyclic voltammograms were recorded with a PAAR EG&G model 283 potentiostat, using an airtight, light-protected, single-compartment cell placed in a Faraday cage.…”

Section: Methodsmentioning

confidence: 99%

“…[2][3][4] Because of the biological activity of these compounds, various synthetic investigations have been carried out with the aim of obtaining new classes of antiviral, antifungal, and antibacterial agents containing the pharmacophoric 1,2-dithiin group. 5,6 Furthermore, the explanation of the intense red-to-orange color in the absence of a conventional chromophore and the 8-π-electron anti-aromatic ring system have been interesting subjects of theoretical consideration.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structures and Electronic Transitions of 3,6-Diphenyl-1,2-dithiin and Its Radical Cation: A Spectroelectrochemical and DFT Study

et al. 2006

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One-electron oxidation of 3,6-diphenyl-1,2-dithiin yields the corresponding radical cation. The product is stable at low temperatures and can be distinguished by a triplet EPR signal. Cyclic voltammetric, UV-vis spectroelectrochemical, and DFT studies were performed to elucidate its molecular structure and electronic properties. Time-dependent DFT calculations reproduce appreciably well the UV-vis spectral changes observed during the oxidation. The results reveal a moderately twisted structure of the 1,2-dithiin heterocycle in the radical cation.

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“…An interesting photochemical synthesis of 2,5-disubstituted-thiophenes 38 stems from the first report of the photoinduced sulfur extrusion from variously 3,6-disubstituted 1,2-dithiins 35a by exposure to daylight in ethyl acetate or in DCM, or by irradiation at 365 nm in methanol (Scheme 12.11) [29]. Other examples involve naturally occurring thiarubrines 35b [30], as well as variously substituted synthetic derivatives [31].…”

Section: Thiophenesmentioning

confidence: 99%

Synthesis of Heteroaromatics via Rearrangement Reactions

Vivona

Buscemi

Pibiri

et al. 2009

Handbook of Synthetic Photochemistry

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The varied family of heteroaromatics contains a large fraction of organic compounds, many of which have found important applications in different fields. Many synthetic methodologies have been developed to obtain target systems and, among them, photochemical methods represent valid and elegant alternatives when the final targets are difficult to obtain through ground-state chemistry. In this chapter, we describe the photochemical synthesis of heteroaromatic compounds through rearrangement reactions, particularly via ring-transformations of heterocyclic precursors [1][2][3][4][5][6][7].A classification of all photoinduced heterocyclic ring-transformation reactions is quite difficult to achieve due to the large variety of mechanistic pathways, experimental conditions and affecting parameters. In some cases, the photochemical product and the starting substrate have the same heterocyclic nucleus. In this chapter, we will refer to such reactions, characterized by the identity of the starting and final ring, as ring-degenerate rearrangements.In general, photoinduced rearrangements of heterocycles leading to heteroaromatic compounds may involve ring-contraction, internal cyclization, ring-expansion, ring-opening or ring-closure, and ring-fragmentation processes. As for five-membered rings, two processes will be repeatedly quoted throughout this chapter:. The ring contraction-ring expansion route (RCRE), which explains the formal interchange between two adjacent ring-atoms. This results from the photoinduced cleavage of the weakest bond in the ring with formation of a three-membered ring intermediate. The latter is then converted, either thermally or photochemically, into the final five-membered heterocyclic product (see e.g., Scheme 12.22). . The internal cyclization-isomerization route (ICI), which involves the formation of a bicyclic species featuring a single bond between the ring-atoms in the 2-and 5-positions of the original heterocycle. Sigmatropic shifts then occur, leading to different bicyclic intermediates from which the final products will arise (see e.g., Scheme 12.2).Handbook of Synthetic Photochemistry. Edited

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1,2‐Dithiins, a New Type of Heterocycle

Cited by 45 publications

References 6 publications

Microwave Spectra, Molecular Structure, and Electric Dipole Moment of 1,2-Dithiin

Microwave Spectra, Molecular Structure, and Electric Dipole Moment of 1,2-Dithiin

Molecular Structures and Electronic Transitions of 3,6-Diphenyl-1,2-dithiin and Its Radical Cation: A Spectroelectrochemical and DFT Study

Synthesis of Heteroaromatics via Rearrangement Reactions

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