Über <i>o</i>, <i>o</i>′‐Dinitro‐tolan

Kliegl, A.; Haas, K.

doi:10.1002/cber.19110440206

Cited by 23 publications

(11 citation statements)

References 8 publications

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“…[12] 2,2Ј-Dinitrotolane was obtained from 2-nitrobenzal chloride and sodium ethoxide in ethanol. [13] The reduction of 2,2Ј-dinitrotolane to 2,2Ј-diaminotolane was performed by the use of SnCl 2 in acetic acid and ultrasonic irradiation. [14] The physical and spectroscopic parameters of these three compounds were in line with the literature data.…”

Section: Resultsmentioning

confidence: 99%

“…The solution was filtered and the brownish residue was 3 (s, 1 H, N-H) 6.9-7.7 (m, 8 H, C arom -H) ppm. 13 C NMR: δ = 89.0, 95.5 (CϵC), 110.6, 115.4, 119.4, 120.6, 124.3, 128.8, 130.8, 131.2, 132.6, 133.3, 143.8, 152.3 [Co((tolaneN 3 ) 2 )(py) 2 ] (3): Cobalt acetate tetrahydrate (56 mg, 0.25 mmol) and 2 (75 mg, 0.17 mmol) were dissolved in 3 mL of pyridine under slight warming to 50°C in a water bath. The clear, dark red solution was left standing still at ambient temperature.…”

Section: Methodsmentioning

confidence: 97%

“…Care must be taken when 2 is exposed to elevated temperatures. 13,25,26-Tetradehydro-5,18-dihydrotetrabenzo[d,h,m,q]-[1,2,3,10,11,12]hexaazacyclooctadecine (2): In a typical experiment, 3.12 g (15 mmol) 2,2Ј-diaminotolane [13] was suspended in 80 mL of 6  hydrochloric acid. The slurry was cooled to 0°C and a solution o 1.03 g (15 mmol) NaNO 2 in water was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

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A Macrocyclic Bistriazene and its Complexes with Divalent Metal Ions

2009

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The diazotisation of 2,2Ј-diaminotolane with one equivalent of HNO 2 yields the macrocyclic bis(tolanetriazene) (tolaneN 3 H) 2 in moderate yield. As shown by the crystal structure determination, the molecule is essentially planar. After deprotonation, the central cavity is suitable for complexation of transition metal ions. In pyridine solution, the anion (tolaneN 3 ) 2 2-is formed, which reacts with the acetates of Co 2+and Ni 2+ to the dark red coloured complexes [M((tolaneN 3 ) 2 )-(py) 2 ]. The metal ions are located in the centre of the macrocycles, coordinated by four N atoms of the two triazenide

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

A Macrocyclic Bistriazene and its Complexes with Divalent Metal Ions

2009

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“…It has already been applied in advanced investigations directed towards high-spin organic polymers and OLEDs. [40] The subsequent reduction of 38 with tin led to a substance identical to that of Golubews diiminotolane. [37] Because it contains the indole moiety, there is the possibility of biological properties.…”

Section: P-expanded Pyrroloa C H T U N G T R E N N U N G [32-b]pyrrolesmentioning

confidence: 99%

“…Summary and Outlook 1,4-DihydropyrroloA C H T U N G T R E N N U N G [3,2-b]pyrrole, although known for a long time, is only now becoming the subject of intense research. [39][40][41][42] The most efficient method in this regard involves a two-step reduction with Na 2 S and SnCl 2 under acidic conditions. For the preparation of parent 1,4-dihydropyrroloA C H T U N G T R E N N U N G [3,2-b]pyrroles, the Hemetsberger [2,5] and our [11] methods seem to be the most general and straightforward ones.…”

Section: Physicochemical Propertiesmentioning

confidence: 99%

1,4‐Dihydropyrrolo[3,2‐b]pyrrole and Its π‐Expanded Analogues

Janiga

Gryko

2014

Chemistry An Asian Journal

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Various approaches to the synthesis of 1,4-dihydropyrrolo[3,2-b]pyrroles are summarized. Many two- and three-step reaction sequences have been developed, and have allowed access to a broad variety of structures, including not only the parent 1,4-dihydropyrrolo[3,2-b]pyrroles, but also their π-expanded analogues. The newest approaches are critically compared with older strategies. The reactivity of these compounds is also reviewed, with special emphasis on electrophilic aromatic substitution. The synthesis of indolo[3,2-b]indole derivatives has been the subject of intense investigation. Overall, a few interesting and ingenious approaches toward these ladder-type heteroacenes have been proposed, reaching total yields in the region of 30%. Finally, the optical, electrochemical, and other physicochemical properties are presented in the broader perspective of heteropentalenes. The parent 1,4-dihydro-pyrrolo[3,2-b]pyrroles constitute the most electron-rich, simple, aromatic heterocycles, and their simple derivatives and π-expanded analogues possess strong violet, blue, or green fluorescence both in solution and in the solid state.

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The Synthesis of Acetylenes

Jacobs

2011

Organic Reactions

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Many advances have been made in recent years in the methods for the synthesis of acetylenes and many compounds are now rather readily available in the pure state. Acetylene was first prepared by Davy, who treated acetylide with water. Propyne, the first substituted acetylene was obtained in 1861. At the present time alkynes are usually synthesized by the alkylation of sodium acetylide or substituted metallic acetylides, often in liquid ammonia and 1‐Alkynes are also obtained by dehydrohalogenation of suitable halides with sodium amide or in certain cases by ethanolic alkali. The present discussion will be limited to methods for the creation of a carbon‐carbon triple bond and to the alkylation of metallic acetylides.

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Über o, o′‐Dinitro‐tolan

Cited by 23 publications

References 8 publications

A Macrocyclic Bistriazene and its Complexes with Divalent Metal Ions

A Macrocyclic Bistriazene and its Complexes with Divalent Metal Ions

1,4‐Dihydropyrrolo[3,2‐b]pyrrole and Its π‐Expanded Analogues

The Synthesis of Acetylenes

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