New synthesis of 1,3-dithiole-2-thiones

Benitez, Francisco M.; Grunwell, John R.

doi:10.1021/jo00408a037

Cited by 12 publications

(6 citation statements)

References 6 publications

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“…2-Thioxo-1,3-dithioles 323, which are good precursors of tetrathiafulvalenes upon dimerization-desulfurization, can also be obtained from DMAD, carbon disulfide and either bis(2,2,6,6-tetramethylpiperidine) disulfide or bis(morpholino) disulfide 322 at 140°C under nitrogen. 109 This methodology is not restricted to electrophilic alkynes since it also works with terminal alkynes. A mechanism involving a 1,3-dipolar cycloaddition between carbon disulfide and a transient thioketocarbene was proposed (Scheme 91).…”

Section: Scheme 90mentioning

confidence: 99%

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Neochoritis

Zarganes‐Tzitzikas

Stephanidou‐Stephanatou

2014

Synthesis

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This review presents the recent progress in the chemistry of dimethyl acetylenedicarboxylate (DMAD). The interest in and applications of this powerful reagent with more than 135 years of history have greatly increased in the last 10 years, further proving its versatility. Undoubtedly, DMAD can be a multi-tool in the quest of molecular complexity and diversity. The extreme structural diversity of the products described in this review illustrates the powerful potential of DMAD as a building block in organic synthesis.

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Section: Scheme 90mentioning

confidence: 99%

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Neochoritis

Zarganes‐Tzitzikas

Stephanidou‐Stephanatou

2014

Synthesis

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“…Methyl phenylpropiolate 4 was obtained (40.5% yield) via reaction of phenyl acetylene 3 with methyl chloroformate in the presence of sodium metal as shown in Scheme 1. Scheme 1 The synthetic strategy described by Benitez and Grunwell for the preparation of 1,3-dithiole-2-thione derivative 5a [17] was adapted for compound 5b as shown in Scheme 1. Treatment of Phenyl acetylene 3 or related ester 4 with carbon disulfide at 140 °C using an autoclave in the presence of bis-morphiline disulfide gave the corresponding 1,3-dithiole-2-thione derivatives 5a-b as shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…4-Phenyl-1,3-dithiole-2-thione (5a) was obtained according to the reported method as yellow crystals in 44% yield, mp 117-118 °C, lit. 117-118 °C [17].…”

Section: Chartmentioning

confidence: 99%

“…Following the method reported in reference [17], a mixture of methyl phenylpropiolate (4; 2.73 g, 17 mmol) and bis-morphiline disulfide (1.0 g, 4.0 mmol) in a 4:1 molar ratio was dissolved in 75 ml of CS 2 , and the resulting solution was poured in a one liter Parr bomb reactor (autoclave). The apparatus was flushed with N 2 and heated to 140 °C for 24 hours.…”

Section: -Methoxycarbonylmentioning

confidence: 99%

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Synthesis and electrochemical studies of tetrathiafulvalene derivatives (TTFs) as redox active ligands

Sarhan

Murakami

Izumi

2002

Journal of Heterocyclic Chem

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A simple route for synthesis of new tetrathiafulvalene dimethyl ester (TTF-DME) is reported. The tetrathifulvalene dimethylester (TTF-DME) has been prepared by introducing an ester coordination function as a bifunctional new donor. The redox behavior of the TTF-DME was investigated in comparison to the well-known dibenzotetrathiafulvene (DB-TTF) by cyclic voltammetry. A two-electron redox behavior was observed as a two waves.

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“…Initial addition of the thionitroxyl radical to the alkyne gave an intermediate radical, which led to thioketocarbene that in turn captures carbon disulfide to give the product (Scheme 41). 56…”

Section: Synthesis Of 13-dithiolsmentioning

confidence: 99%