Ueber die Einwirkung aromatischer Amine auf Aethylendisulfochlorid und über Vinylsulfonderivate

Autenrieth, W.; Koburger, Julius

doi:10.1002/cber.190303603162

Cited by 9 publications

(8 citation statements)

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“…As noted in the introduction there are a number of reports, some dating back to the previous century, describing unexpected reactions of 1,2-ethanedisulfonyl and 2-chloroethanesulfonyl chlorides (li and lj) (15)(16)(17)(18)(19)(20)(21)(22). With nucleo-'Orthodox substituent effects have been observed in at least one sulfene-generating reaction: the rates of formation of ArCH=S02 from ArCH2S020--C6H3-2,4(N02)2 in an (ElcB), reaction process showed an excellent correlation with u-(with p-2.38, r = 0.996) (13).…”

Section: Earlier Reports Of the Anomalous Reactions Of I I And Ijmentioning

confidence: 99%

“…philes of the general formula ZH, such as water, alcohols, or amines, the major products of these reactions were never the orthodox derivatives, ZS02CH2CH2S02Z or C1CH2CH2SO2Z, but rather the ethenesulfonate, CHy==CHS02Z, or the formal product of further addition of ZH, i.e., ZCH2CH2S02Z; thus (a) l i with hot water gives mainly SO2, HCl, and CH-----CHS03H (15,17,22), and (b) lj with aniline yields CHF CHS02NHPh (8) and (or) PhNH2+CH2CH2S02NHPh C1-(9) (16)(17)(18)(19)(20)(21). In the light of the present work it is highly likely that these products arise by initial formation of ethenesulfonyl chloride (2) followed by vinylogous reaction to form the sulfene 3 (X = Z+).…”

Section: Earlier Reports Of the Anomalous Reactions Of I I And Ijmentioning

confidence: 99%

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Nucleofugality effects in the pyridine promoted formation of esters from 2-substituted ethanesulfonyl chlorides

King¹,

Hillhouse²,

Lauriston³

et al. 1988

Can. J. Chem.

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109 (1988). The products of reaction of a series of 10 2-substituted ethanesulfonyl chlorides, X-CH2CH2S02C1 (I), with neopentyl alcohol and pyridine-d5 in nitromethane-d3 showed three reaction pathways depending on the nucleofugality of the substituent, X. These routes lead, respectively, to (i) the corresponding neopentyl ester (4), via the sulfene (3) (low substituent nucleofugality); (ii) a mixture of ester 4 and neopentyl ethenesulfonate (5), by the same route except for a partial loss of the 2-substituent during trapping of the sulfene (3) (intermediate nucleofugality); and (iii) a mixture of the ethenesulfonate (5) and the pyridino-betylate (4g) esters, arising from initial elimination of HX to form ethenesulfonyl chloride (2) followed by its further reaction (high substituent nucleofugality). A set of nucleofugality values closely related to, and partly complementing, those derived by Stirling and co-workers can be estimated from the product ratios in those reactions proceeding (at least in part) by route (ii) above. Old reports of anomalous products from 1,2-ethanedisulfonyl chloride (li) and 2-chloroethanesulfonyl chloride (lj) are simply accounted for on the basis of the initial conversion to ethenesulfonyl chloride (2).JAMES FREDERICK KING, JOHN HENRY HILLHOUSE, TOYANNE MARIE LAURISTON et KISHAN CHAND KHEMANI. Can. J. Chem. 66, 1109Chem. 66, (1988.Les produits provenant des rkactions d'une sCrie de 10 chlorures d'tthanesulfonyle substituCs en position 2, X-CH2CH2S02CI (I), avec I'alcool nCopentylique et la pyridine-ds, dans le nitromkthane-d3 proviennent de trois voies differentes qui dtpendent de la nuclCofugacitt du substituant X. Ces voies conduisent respectivement 21 (i) ester nCopentylique correspondant (4), par la biais du sulfene 3 (lorsque la nuclCofugacitC du substituant est faible); (ii) un milange de I'ester 4 et I'tth2nesulfonate de ntopentyle (5) qui proviennent de la m&me voie, except6 pour la perte partielle du substituant en position 2 qui se produit lors du piCgeage du sulf5ne 3 (lorsque la nuclCofugacit6 du substituant est intermkdiaire); et (iii) un melange des esters Cth5nesulfo-nate (5) et pyridinio-Etylate (4g) qui proviennent d'une Climination initiale de HX, conduisant au chlorure d'Cth5nesulfonyle (2), qui est suivie de sa &action (lorsque la nuclCofugacitC du substituant est ClevCe). En se basant sur les rapports des produits qui se foment au cours des rkactions (au moins en partie) qui suivent la voie (ii) mentionnCe plus haut, on peut tvaluer un ensemble de valeurs de nucltofugacitt qui ressemble et qui compl2te celui de Stirling et ses collaborateurs. Des rapports antCrieurs concernant la formation de produits anormaux a partir des chlorures d'Cthanedisulfonyle-1,2 (li) et de chloro-2 Cthanesulfonyle (lj) peuvent facilement &tre expliquCs en se basant sur une conversion initiale en chlorure d'eth2nesulfonyle (2).[Traduit par la revue] 1

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Section: Earlier Reports Of the Anomalous Reactions Of I I And Ijmentioning

confidence: 99%

Section: Earlier Reports Of the Anomalous Reactions Of I I And Ijmentioning

confidence: 99%

Nucleofugality effects in the pyridine promoted formation of esters from 2-substituted ethanesulfonyl chlorides

King¹,

Hillhouse²,

Lauriston³

et al. 1988

Can. J. Chem.

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“…The classical approach to prepare this moiety involves the reaction between amine nucleophiles and sulfonyl chlorides (Figure 1A). 2,3 However, sulfonyl chlorides are not widely available and are toxic, unstable reagents. Their preparation is cumbersome and requires a combination of oxidizing and chlorinating reagents.…”

mentioning

confidence: 99%

“…Switching to sulfuric acid gave slightly lower yields compared to 2 Pyridine (2.0 mmol) was added as an additive. 3 The corresponding disulfide was used as starting material. 4 hydrochloric acid (entry 4).…”

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confidence: 99%

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Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

et al. 2019

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Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.

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Ueber die Methionsäure

Schroeter

Herzberg

1905

Ber. Dtsch. Chem. Ges.

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Ueber die Einwirkung aromatischer Amine auf Aethylendisulfochlorid und über Vinylsulfonderivate

Abstract: Aether; von concentrirter Schwefel-oder Salz-Saure wird intensiv gelber Farbe, wie die RosindonsBnre, aufgenommen.Sie gab nach dem Trocknen bei 1200 folgende Zahlen: CO2, 0.0430 g HaO. -0.1336 g Sbst.: 12.2 ccm N (160, 736 mm). 0.12.56 g Sbst.: 0.3147 g COa, 0.0469 g HsO. -0.119Og Sbst.:

Cited by 9 publications

References 1 publication

Nucleofugality effects in the pyridine promoted formation of esters from 2-substituted ethanesulfonyl chlorides

Nucleofugality effects in the pyridine promoted formation of esters from 2-substituted ethanesulfonyl chlorides

Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols

Ueber die Methionsäure

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