Ketenderivate, XII. Beiträge zur Chemie der Dithiocarbonsäureester und Ketenmercaptale

Gompper, Rudolf; Schaefer, Hartmann

doi:10.1002/cber.19671000228

Cited by 183 publications

(36 citation statements)

References 19 publications

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“…Compound 12 was first obtained by Kelber (6) by treatment of acetophenone with carbon disulfide and base to give benzoyldithioacetic acid (ll), followed by methylation with methyl iodide and sodium; in the present work it was also prepared by methylation of 11 with methyl iodide and sodamide or with diazomethane. Its structure was confirmed by our spectroscopic observations and those of Gompper and Schaefer (7), and by an X-ray crystallographic study by Nyburg and Mellor (8).…”

supporting

confidence: 75%

Carbon Disulfide. III. Reaction with Active Methylene Compounds. The Infrared and Ultraviolet Spectra of the Desaurins

Yates¹,

Lynch²,

Moore³

1971

Can. J. Chem.

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The position of the carbonyl-stretching bands in the i.r. spectra of the desaurins, 2,4-bis(acy1methy-1ene)-and 2,4-bis(carboxymethy1ene)-l,3-dithetane derivatives, establishes that there is a strong interaction between the sulfur atoms and the carbonyl groups. This is considered to involve mainly conjugative interaction rather than interaction through space, although the latter may account for the abnormally weak intensity of the carbonyl-stretching bands. These bands are split in the case of several desaurins and related compounds, and evidence has been obtained in one case that the splitting is due to Fermi resonance. The U.V. spectra of the desaurins and related compounds also indicate a strong conjugative interaction between the sulfur atoms and the carbonyl groups.La position des bandes de vibration des carbonyles dans les spectres i.r. des disaurines, des derives des bi'sf~ylmethy1ene)-2,4 et bis(carboxymCthy1ene)-2,4 diethane-1,3, dtmontre qu'il existe une interaction forte entre les atomes de soufre et les groupes carbonyles. Ces rksultats proviendraient principalement d'une interaction conjugative plut6t que d'une interaction a travers I'espace, quoique cette derniere hypothese pourrait expliquer l'intensitk anormalement faible des bandes de vibration des carbonyles. Dans le cas de plusieurs dksaurines et composCs analogues, les bandes sont diviskes et des indications ont Cte obtenues dans un cas, que cette division est due a de la resonance de Fermi. Les spectres ultraviolets des dksaurines et des composes voisins indiquent aussi qu'une interaction conjugative forte existe entre les atomes de soufre et les groupes carbonyles. 's' these desaurins, it was considered to be of importance to compare them with the spectra of a desaurin derived from a dialkyl ketone. For personal use only.

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supporting

confidence: 75%

Carbon Disulfide. III. Reaction with Active Methylene Compounds. The Infrared and Ultraviolet Spectra of the Desaurins

Yates¹,

Lynch²,

Moore³

1971

Can. J. Chem.

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“…Die p-Alkoxyacetophenone P-Hi,-iC"0-C6H4-C (0 )-C H 3 (n = 1-16), die zunächst aus p-Hydroxyacetophenon mit den ent sprechenden Alkylbromiden in Aceton mit K2C 0 3 als Base hergestellt werden, reagieren mit CS2/KO?Bu in Ether zu den 1,1-Ethendithiolaten [5]. Gibt man zu diesem Gemisch Wasser, so ent steht eine schwer trennbare Emulsion, die erst durch Zentrifugieren gebrochen werden kann.…”

Section: Ergebnisse Und Diskussionunclassified

Funktionalisierte 1,1-Ethendithiolate als Liganden, II / Functionalized 1,1-Ethene Dithiolates as Ligands, II

Weigand¹,

Saumweber²,

Schulz

1993

Zeitschrift Für Naturforschung B

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“…Differently substituted 3,3-diamino-N-aryl-2-nitrothioacrylamides 11, prepared from nitroketene dithioacetal9 (in the case of R' = R2) [29] or from 10 (in the case of R' # R2) [29] [30] (cf [15]) by consecutive treatment with a primary amine and an aryl isothiocyanate, were treated with diethyl azodicarboxylate (DEAD) in DMF at room temperature. The isothiazol-5(2H)-imines 12 were formed via an oxidative intramolecular cyclization (Scheme 3, Table I) [31].…”

Section: Synthesis Of N-aryl-3-amino-4-nitroisothiazol-5(2h)-imines 12mentioning

confidence: 99%

“…See [27]. The starting 2-nitroethene-1,l-diamines were synthesized according to the general procedures described in [I71 [29] [30]. An improved synthesis of the 3,3-diamino-2-nitrothioacrylamides (= 3,3-diamino-2-nitroprop-2-enethioamides) 11 has already been reported by us [24].…”

mentioning

confidence: 99%

An Unexpected Isomerization of N‐Aryl‐3‐amino‐4‐nitroisothiazol‐5(2H)‐imines to 2‐(Benzothiazol‐2‐yl)‐2‐nitroethene‐l, l‐diamines

Argilagos

Trimino²,

Cabrera³

et al. 1997

Helvetica Chimica Acta

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The syntheses of several N-aryl-3-amino-4-nitroisothiazol-5(2H)-imines 12 from 3,3-diamino-2-nitrothioacrylamides 11 are reported (Scheme 3). In polar solvents, a spontaneous isomerization of some of the prepared isothiazol-5(2H)-imines 12 yielded benzothiazoles 13 (Scheme 4). In the case of 2-alkyl-substituted derivatives of type 12, the isomerization occurred only at higher temperatures. Electronic influences of different substituents on the rate of the isomerization were studied, and a polar reaction mechanism is proposed in Scheme 6. The structures of 12e and 13e were established by X-ray crystallography. Conformational analyses of 3-(methylamino)-2-nitro-N-phenyl-3-(pyrrolidin-l-yl)thioacry~amide (1 1 I) by NMR and X-ray methods were performed with the aim of explaining the distinct behavior of this amide towards Br, or diethyl azodicarboxylate.

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Ketenderivate, XII. Beiträge zur Chemie der Dithiocarbonsäureester und Ketenmercaptale

Cited by 183 publications

References 19 publications

Carbon Disulfide. III. Reaction with Active Methylene Compounds. The Infrared and Ultraviolet Spectra of the Desaurins

Carbon Disulfide. III. Reaction with Active Methylene Compounds. The Infrared and Ultraviolet Spectra of the Desaurins

Funktionalisierte 1,1-Ethendithiolate als Liganden, II / Functionalized 1,1-Ethene Dithiolates as Ligands, II

An Unexpected Isomerization of N‐Aryl‐3‐amino‐4‐nitroisothiazol‐5(2H)‐imines to 2‐(Benzothiazol‐2‐yl)‐2‐nitroethene‐l, l‐diamines

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