Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaO<i>t</i>Bu

Zhang, Guoting; Yi, Hong; Chen, Hong; Bian, Changliang; Liu, Chao; Lei, Aiwen

doi:10.1021/ol503015b

Cited by 160 publications

(78 citation statements)

References 38 publications

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“…Considering that ferrocenyl amide (1) and methyl ferrocene carboxylate (8) could be detected under the standard reaction conditions (Scheme 4, 6a), the reactions of 1 and 8 with 2a were performed in the presence of external sulfur sources, such as S 8 , NaHS$H 2 O and Na 2 S$9H 2 O, respectively. [42][43][44] However, 6a was not observed (Scheme 5c and d). The cycloaddition reaction of 4 did not occur in the presence of additional sulfur sources (Scheme 5e).…”

Section: Resultsmentioning

confidence: 98%

Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties

Yan

Lan

et al. 2020

Chem. Sci.

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Section: Resultsmentioning

confidence: 98%

Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties

Yan

Lan

et al. 2020

Chem. Sci.

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“…These results suggest that molecular iodine is an effective oxidant for such a transformation. Other oxidants, including DDQ, BQ, TBHP, DTBP, DCP, and H 2 O 2 , were also effective (table 1, entries [12][13][14][15][16][17], but gave much lower yields than K 2 S 2 O 8 . In these reactions, a certain amount of amide was formed, and compound 1 a could not be converted to the corresponding product completely.…”

Section: Resultsmentioning

confidence: 99%

“…In the reaction with elemental sulfur, the trisulfur radical anion C may be formed at 120°C. [16] Next, intermediate B reacts with C to provide an intermediate D,…”

Section: Resultsmentioning

confidence: 99%

Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application

Huang

Guo

et al. 2020

Asian J Org Chem

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Primary thioamides are useful building blocks for drug and insecticide development, therefore an environmentally benign synthesis of primary thioamides is desired. This paper discloses an oxidative thiolysis for the selective transformation of nitriles into primary thioamides using elemental sulfur or thiuram in the presence of K2S2O8 in DMF/H2O. This practical method enables access to a wide range of synthetically and pharmaceutically useful primary thioamides. Advantages of this reaction include transition‐metal‐free and base‐free reaction conditions, use of an environmentally benign solvent (DMF/H2O) system, the use of non‐toxic elemental sulfur or thiuram as the sulfur sources, and good functional groups tolerances with excellent selectivity. Furthermore, the insecticide Fipronil can also be converted to the corresponding thioamide and maintains excellent bioactivity against P. xylostella. The LC50 value of Fipronil thioamide is 1.25 mg/L.

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“…[75][76][77] Such transformation may be also applied for polyynes. [75][76][77] Such transformation may be also applied for polyynes.…”

Section: Formation Of Heterocyclesmentioning

confidence: 99%

Reactivity of Polyynes: Complex Molecules from Simple Carbon Rods

2019

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Polyynes are linear carbon rods that may be regarded as models of carbyne – still elusive linear allotropic form of carbon. This microreview addresses the use of polyynes as synthetic precursors of complex organic and organometallic compounds. Application of such unusual molecules as starting materials for various chemical transformations leads to products which often are not easily accessible using “traditional“ approaches. Polyynes may for instance be used in the synthesis of molecular wires, materials possessing high nonlinear optical response, complex donor–acceptor systems, solvatochromic fluorescent dyes or natural products. The most significant challenge here is to control the regioselectivity of a transformation of such linear sp‐hybridized carbon chains. The impact of steric and electronic properties of reagents on the reaction pattern is hence highly important and will be discussed. Moreover, the transformations of end‐groups will also be addressed since their reactivity might very often be different than that of acetylenes.

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Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaOtBu

Cited by 160 publications

References 38 publications

Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties

Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties

Selectively Oxidative Thiolysis of Nitriles into Primary Thioamides and Insecticidal Application

Reactivity of Polyynes: Complex Molecules from Simple Carbon Rods

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