A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized by Buttressing and Resonance Effects, Respectively, by Sulfuration of Alkynes with Elemental Sulfur

Choi, K. S.; Akiyama, Isao; Hoshino, Minoru; Nakayama, Juzo

doi:10.1246/bcsj.66.623

Cited by 53 publications

(10 citation statements)

References 34 publications

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“…Herein, we report a simple thienannulation protocol, in which arylethynyl-substituted PAHs are heated in DMF in the presence of elemental sulfur to afford the corresponding thiophene-fused PAHs via cleavage of the ortho -C–H bond. This reaction requires the presence of only one functional group, i.e., an arylethynyl group on the PAHs.…”

Section: Introductionmentioning

confidence: 99%

Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur

et al. 2016

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A simple yet effective method for the formation of thiophene-fused π-systems is reported. When arylethynyl-substituted polycyclic arenes were heated in DMF in the presence of elemental sulfur, the corresponding thiophene-fused polycyclic arenes were obtained via cleavage of the ortho-C-H bond. Thus, arylethynylated naphthalenes, fluoranthenes, pyrenes, corannulenes, chrysenes, and benzo[c]naphtho[2,1-p]chrysenes were effectively converted into the corresponding thiophene-fused π-systems. Apart from polycyclic hydrocarbons, thiophene derivatives are also susceptible to this reaction. The practical utility of this reaction is demonstrated by preparations on the decagram scale, one-pot two-step reaction sequences, and multiple thiophene annulations.

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Section: Introductionmentioning

confidence: 99%

Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur

et al. 2016

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“…We propose that the copolymerization proceeded with the initial formation of a dithiolodithiole (1, Scheme 1) that subsequently rearranges to form a 2,5-diphenylthiophene with bridging S-S connectivity at the 3 and 4 positions (Scheme 1). Elucidating the structure of the resulting copolymer and gaining insight into the course of the copolymerization was challenging due to the broad range of possible products and isomers that have been alluded to in the literature upon sulfurization of (bis)alkynes, [29][30][31][32][33] along with broad resonances observed in both 1 H and 13 C NMR spectroscopies. Initial NMR experiments revealed the presence of diphenyldithiolodithiole as a component of the reaction mixture generated upon inverse vulcanization of S 8 with low loadings of DiPhDY (i.e.…”

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confidence: 99%

Inverse vulcanization of elemental sulfur with 1,4-diphenylbutadiyne for cathode materials in Li–S batteries

et al. 2015

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High sulfur content copolymers were prepared via inverse vulcanization of sulfur with 1,4-diphenylbutadiyne (DiPhDY) for use as the active cathode material in lithium-sulfur batteries. These sulfur-rich polymers exhibited excellent capacity retention (800 mA h g À1 at 300 cycles) and extended battery lifetimes of over 850 cycles at C/5 rate. Fig. 3 (a) Cycling performance at C/5 of Li-S battery fabricated with poly(S-co-DiPhDY) prepared with a 10 wt% DiPhDY, 90 wt% sulfur feed ratio. (b) Plot of potential versus charge/discharge capacity for the Li-S cell shown in (a) at 100 cycle intervals. (c) Charge/discharge rate performance of Li-S battery with poly(S-co-DiPhDY) (10 wt% DiPhDY) at various current densities (1 C ¼ 1672 mA h). All capacities are specific capacity based on sulfur loading.This journal is

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“…Recently, we have reported the synthesis of 1,3,2-dithiaphospholes from 1,2-dithietes, which was considered to involve a 1,2-ethenedithiolato rhodium intermediate . When 3-( tert -butyl)-4-phenyl-1,2-dithiete 16 was reacted with excess 3 (20 equiv) in the presence of RhH(dppe) 2 (10 mol %) at 130 °C for 6 h, 5-( tert -butyl)-2,3-di(methoxycarbonyl)-4-phenylthiophene 17 (60%) was obtained, which was accompanied by 10 (60%) (Scheme ). The structure of 17 was determined by X-ray crystal structure analysis (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Isomerization and Alkyne Exchange Reactions of 1,4-Dithiins via the 1,2-Ethenedithiolato Rhodium Complex

et al. 2018

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Rhodium-catalyzed isomerization and alkyne exchange reactions of 1,4-dithiines occurred by cleavage of two C−S bonds. The 2,5-and 2,6-disubstituted 1,4-dithiins underwent isomerization reactions in toluene at 110 °C, providing equilibrium mixtures of isomers. At 150 °C, the reaction of 1,4dithiins and dimethyl acetylenedicarboxylate gave unsymmetric 2 , 3 -d i ( m e t h o x y c a r b o n y l ) -1 , 4 -d i t h i i n s a n d 2 , 3 -d i -(methoxycarbonyl)thiophenes, the latter of which were formed by desulfurization of the 1,4-dithiins. A related reaction of the alkyne and a 1,2-dithiete gave a 2,3-di(methoxycarbonyl)thiophene. These reactions are considered to involve 1,2ethenedithiolato rhodium intermediates.

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A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized by Buttressing and Resonance Effects, Respectively, by Sulfuration of Alkynes with Elemental Sulfur

Cited by 53 publications

References 34 publications

Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur

Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur

Inverse vulcanization of elemental sulfur with 1,4-diphenylbutadiyne for cathode materials in Li–S batteries

Rhodium-Catalyzed Isomerization and Alkyne Exchange Reactions of 1,4-Dithiins via the 1,2-Ethenedithiolato Rhodium Complex

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