Cyclic polysulfides fused to polyaromatics

Alam, Ashraful; Konno, Masaki; Ogawa, Satoshi; Sato, Ryo

doi:10.1016/j.tet.2006.11.026

Cited by 14 publications

(4 citation statements)

References 31 publications

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“…This strategy of o ‐lithiation assisted thiolation applied to fused polyaromatic thiols derived from naphthalene and phenanthrene led to products with different polysulfur ring sizes and regiochemistry . When 2‐naphthalenethiol 136 was treated with excess n ‐BuLi, the resulting dilithio salt 137 could be transformed into pentathiepin 138 according to the two following pathways (Scheme ).…”

Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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“…[6b, 11,17] Therefore, we wished to explore unstable cyclic polychalcogenides at the C 2 -C 3 position. 2-Naphthalenethiol was used to synthesize the target ring system according to Scheme 3; it was converted into 2,2-dimethylnaphtho [2,3- (11) by a sequential chemical process, such as lithiation with nBuLi (4 equiv.…”

Section: Synthesis Of Naphtho[12345]tetrathiaselenepinsmentioning

confidence: 99%

“…The construction of the same ring was also established at the C 1 -C 2 position although this position is more liable to bear cyclic polysulfides. [11] Lithiation of 1-naphthalenethiol has already been performed. [12] Selenation of a lithiated mixture of 1-naphthalenethiol and successive air oxidation afforded the well-known naphtho [1,8-cd]-1,2-selenathiole (13) in 30 % yield along with some insoluble oligomers (Scheme 4).…”

Section: Synthesis Of Naphtho[12345]tetrathiaselenepinsmentioning

confidence: 99%

“…Phenanthro [9,10-d][1,3,2]thiaselenastannole (16) was synthesized by an established procedure. [11] Lithiation occurred predominantly at the peri positions of phenanthrene; hence, compound 16 was isolated in low yield (4 %). Interestingly, sulfurization of 16 with S 8 /NH 3 afforded two products, 17 and 18, in 21 and 46 % yields, respectively (Scheme 5).…”

Section: Synthesis Of Naphtho[12345]tetrathiaselenepinsmentioning

confidence: 99%

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Selenium‐Containing Tetrachalcogenins and Pentachalcogenepins Fused to Aromatic Systems

et al. 2007

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Various ring-sized cyclic polychalcogenides fused to aromatic systems were synthesized, and the structures were sufficiently characterized. Stabilities of the rings were examined in terms of the existence of selenium atoms. Benzopolychalcogenides are unstable molecules. However, benzo[1,2,3,4,5]-tetrathiaselenepins with an isopropyl group or two methoxy groups on the ring were found to be stable. Similarly, the novel benzo[2,3,4,1,5]trithiadiselenepin ring was also stabilized by two methoxy groups. Benzo[1,2,3,4]trithiaselenin and benzo[2,3,1,4]dithiadiselenin were also synthesized by a controlled reaction with S 2 Cl 2 at -78°C. The ring systems were sensitive to air, moisture, light, and polar solvents. Extended π-systems such as naphthalene and phenanthrene showed remarkable thermodynamic stability toward un-

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