Synthesis, Properties, Oxidation, and Electrochemistry of 1,2-Dichalcogenins

Block, Eric; Birringer, Marc; DeOrazio, Russell J.; Fabian, Jürgen; Glass, Richard S.; Guo, Cunlan; He, Chunhong; Lorance, Edward; Qian, Quangsheng; Schroeder, Thomas B. H.; Shan, Zhixing; Thiruvazhi, Mohan; Wilson, George S.; Zhang, Xing

doi:10.1021/ja994134s

Cited by 72 publications

(60 citation statements)

References 82 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some of these hexa-heterocycle systems have been intensively investigated [1]. Two of these 1,2-dichalcogenins, dithiin, and diselenin and their derivatives have been synthesized and/or extracted from plants [2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Pseudo Jahn-Teller origin of instability of planar configurations of hexa-heterocycles. Application to compounds with 1,2- and 1,4-C4X2 skeletons (X = O, S, Se, Te)

2015

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Pseudo Jahn-Teller origin of instability of planar configurations of hexa-heterocycles. Application to compounds with 1,2- and 1,4-C4X2 skeletons (X = O, S, Se, Te)

2015

View full text Add to dashboard Cite

“…Other examples involve naturally occurring thiarubrines 35b [30], as well as variously substituted synthetic derivatives [31]. This photochemical reactivity has been generalized with an application in the synthesis of selenophene 40 obtained in almost quantitative yield from 39 [32]. a: R 1 = R 2 = aryl b: R 1 = Me(C C) n (n = 1,2); R 2 = (C C) n CH=CH 2 (n = 1,2) lamp, Pyrex filter), of pyrazinium-N-imides 41 (Scheme 12.12) [33].…”

Section: Thiophenesmentioning

confidence: 99%

Synthesis of Heteroaromatics via Rearrangement Reactions

Vivona

Buscemi

Pibiri

et al. 2009

Handbook of Synthetic Photochemistry

View full text Add to dashboard Cite

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

show abstract

“…The facile light-induced extrusion of sulfur in 1,2-dithiins yielded thiophenes (Scheme 6). [12] Scheme 6.…”

Section: Five-membered Rings With One Heteroatommentioning

confidence: 99%

“…Some of these substrates afforded dithiins as the major products in their reactions with S 2 Cl 2 , as shown in Scheme 6. [12] …”

Section: Dithiinsmentioning

confidence: 99%

Heterocyclic Chemistry of Sulfur Chlorides – Fast Ways to Complex Heterocycles

Garcı́a-Valverde

Torroba

2006

Eur J Org Chem

View full text Add to dashboard Cite

This microreview highlights the most important advances in the synthetic applications of sulfur dichloride and disulfur dichloride for the preparation of heterocycles. Sulfur chlorides can be considered some of the best sulfur‐transfer reagents for the synthesis of heterocyclic systems. Their high reactivity towards nucleophilic organic compounds such as alkenes, alkynes, amines, nitriles, oximes, and their both chlorinating and sulfurating character explain the extensive use of these reagents. In many cases, the initial reactions give rise to reactive intermediates that can be trapped by nucleophiles in a tandem fashion, expanding the possibilities of the reactions. In this way, several new heterocyclic systems can be obtained by a careful selection of the appropriate combination of reagents. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

show abstract

Synthesis, Properties, Oxidation, and Electrochemistry of 1,2-Dichalcogenins

Cited by 72 publications

References 82 publications

Pseudo Jahn-Teller origin of instability of planar configurations of hexa-heterocycles. Application to compounds with 1,2- and 1,4-C4X2 skeletons (X = O, S, Se, Te)

Pseudo Jahn-Teller origin of instability of planar configurations of hexa-heterocycles. Application to compounds with 1,2- and 1,4-C4X2 skeletons (X = O, S, Se, Te)

Synthesis of Heteroaromatics via Rearrangement Reactions

Heterocyclic Chemistry of Sulfur Chlorides – Fast Ways to Complex Heterocycles

Contact Info

Product

Resources

About