Zur Molekülverknüpfung mit Schwefelchloriden. VI. Die Reaktion von Dichlorsulfan mit Thiocarbamidsäureestern

Mühlstädt, M.; Widera, R.

doi:10.1002/prac.19783200115

Cited by 6 publications

(3 citation statements)

References 7 publications

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“…Die rnit der intramolekularen Substitutionsreaktion der Sulfenylchloride 2 konkurrierende 1,ZAddition an ein weiteres Molekul Allylphenylether unter Bildung von entsprechenden Bis-(6-chloralky1)-sulfanen (Einschubaddition) [7]…”

Section: Investigations On the Chemistry Of 3-chloromethyl-3-methyl-2unclassified

“…C 61,19 H 6,16 S 16,34 (196,26) Gef. C 60,78 H 6,15 S 15,21 MS (m/e) : 196 (M') lH-NMR(300MHz) : 7,74 (m,aromat. H),4,38 (d) u.…”

Section: C10h1202sunclassified

“…farbloses, zahes 0 1 C~O H~~N O~S~ Ber. C 58,65 H 6,64 N 3,43 S 15,66 (409,54) Gef 3/150,35 (9),127,1/125,46/125,53 (5,7), 122,0/121, 9 (6), 118,l (8), 117,6/117,3 (lo), 71,4/70,9 (2), 49,8/49,6 (12a)), 43,5/43,4 (3),21,4/21,3 (ll),4/216,2 (2'),58,83/58,81 (l'),49,1/49,2 48,44/48,41 (7'),42,6 (3',4'),26,8/26,1 (5',6'),19,7/19,6/19,5 (8',9')…”

Section: Darstellung Des Camphersulfonamids (13)mentioning

confidence: 99%

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Untersuchungen zur Chemie von 3-Chlormethyl-3-methyl-2,3-dihydro-1,4-benzoxathiinen

et al. 1995

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Investigations on the Chemistry of 3‐Chloromethyl‐3‐methyl‐2,3‐dihydro‐1,4‐benzoxathiines A series of 3‐chloromethyl‐2,3‐dihydro‐1,4‐benzoxathiines 3 were prepared by the reaction of several β‐methallylphenylethers 1 with sulfur dichloride. In some cases intermediate sulfenyl chlorides 2 were isolated and characterized as substituted thiazolidin‐2‐ones. The thermal regioisomerization of selected sulfenyl chlorides and one of the thiazolidinone products was achieved. Starting from 3‐chloromethyl‐2,3‐dihydro‐1,4‐benzoxathiine 3o several derivatives were obtained by nucleophilic displacement at the 3‐chloromethyl position, activated by S‐3‐neighboring group partizipation. The structure of the 3‐acetoxymethyl derivative was determined by x‐ray crystal structure analysis. Further special derivation with selected chiral reagents led to diastereomeric compounds. The separation of the diastereomers by crystallization and chromatography was attempted. HPLC‐separation was achieved in one case.

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Section: Investigations On the Chemistry Of 3-chloromethyl-3-methyl-2unclassified

“…C 61,19 H 6,16 S 16,34 (196,26) Gef. C 60,78 H 6,15 S 15,21 MS (m/e) : 196 (M') lH-NMR(300MHz) : 7,74 (m,aromat. H),4,38 (d) u.…”

Section: C10h1202sunclassified

Section: Darstellung Des Camphersulfonamids (13)mentioning

confidence: 99%

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Untersuchungen zur Chemie von 3-Chlormethyl-3-methyl-2,3-dihydro-1,4-benzoxathiinen

et al. 1995

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Cyclisierungsreaktionen β, γ‐ungesättigter Kohlensäurederivate. II. Reaktionen β, γ‐ungesättigter Carbamidsäurederivate mit elektrophilen Reagenzien ‐ Synthese von N‐substituierten Oxazolidin‐2‐onen

Mühlstädt

Widera

1980

J. Prakt. Chem.

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Cyclization Reactions of β,γ‐Unsaturated Derivatives of Carbonic Acid. II. Reactions of β,γ‐Unsaturated Carbamic Acid Esters with Electrophilic Reagents — Synthesis of N‐Substituted Oxazolidine‐2‐ones N,N‐Disubstituted β,γ‐unsaturated urethans have been cyclized to N‐substituted oxazolidine‐2‐ones by dry hydrogen chloride in methylene chloride. The N‐substituted urethan 1a reacts with hydrogen chloride to form the urethan 2a and the 2‐oxazoline 3 Reaction of 1 with bromine yields the corresponding N‐substituted 5‐bromomethyl oxazolidine‐2‐ones 6

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Cyclisierungsreaktionen β, γ‐ungesättigter Kohlensäurederivate. IV [1]. Synthese von N‐substituierten Thiazolidin‐2‐onen und 2‐Alkoxy‐2‐thiazolinen aus β,γ‐ungesättigten Thiocarbamidsäureestern

Mühlstädt

Widera

1981

J. Prakt. Chem.

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Cyclization Reactions of β,γ‐Unsaturated Derivatives of Carbonic Acid. IV. Synthesis of N‐Substituted Thiazolidine‐2‐ones and 2‐Alkoxy‐2‐thiazolines from β,γ‐Unsaturated Thiocarbamic Acid Esters The reaction between N‐substituted β,γ‐unsaturated thiourethans and dry hydrogen chloride or bromine occurs in methylene chloride at room temperature. The thiourethans 1 a–4 a react with hydrogen chloride to give mixtures of corresponding 2‐alkoxy‐2‐thiazolines 6–9 and the thiazolidine‐2‐one 11 a. A useful synthetic route to N‐substituted thiazolidine‐2‐ones 11 is demonstrated by the reaction of N,N‐disubstituted β,γ‐unsaturated thiourethans with hydrogen chloride and bromine. The i.r. and H‐n.m.r.‐data of the compounds are described.

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Zur Molekülverknüpfung mit Schwefelchloriden. VI. Die Reaktion von Dichlorsulfan mit Thiocarbamidsäureestern

Cited by 6 publications

References 7 publications

Untersuchungen zur Chemie von 3-Chlormethyl-3-methyl-2,3-dihydro-1,4-benzoxathiinen

Untersuchungen zur Chemie von 3-Chlormethyl-3-methyl-2,3-dihydro-1,4-benzoxathiinen

Cyclisierungsreaktionen β, γ‐ungesättigter Kohlensäurederivate. II. Reaktionen β, γ‐ungesättigter Carbamidsäurederivate mit elektrophilen Reagenzien ‐ Synthese von N‐substituierten Oxazolidin‐2‐onen

Cyclisierungsreaktionen β, γ‐ungesättigter Kohlensäurederivate. IV [1]. Synthese von N‐substituierten Thiazolidin‐2‐onen und 2‐Alkoxy‐2‐thiazolinen aus β,γ‐ungesättigten Thiocarbamidsäureestern

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