Synthesis of Novel α,β-Unsaturated Sulfonic Acid Derivatives Containing Dithiocarbamate/Xanthate Groups by Ring Opening of an α,β-Unsaturated γ-Sultone

Maryam Khalili Foumeshi; Azim Ziyaei Halimehjani; Petr Beier

doi:10.1055/s-0040-1707970

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(10): 987-990
DOI: 10.1055/s-0040-1707970

letter

Synthesis of Novel α,β-Unsaturated Sulfonic Acid Derivatives Containing Dithiocarbamate/Xanthate Groups by Ring Opening of an α,β-Unsaturated γ-Sultone

Autoren

Maryam Khalili Foumeshi

^aFaculty of Chemistry, Kharazmi University, P.O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran eMail: ziyaei@khu.ac.ir

^bInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic eMail: beier@uochb.cas.cz
Azim Ziyaei Halimehjani∗

^aFaculty of Chemistry, Kharazmi University, P.O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran eMail: ziyaei@khu.ac.ir
Petr Beier∗

^bInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic eMail: beier@uochb.cas.cz

Abstract

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Abstract

An efficient method is disclosed for the synthesis of novel α,β-unsaturated sulfonic acid derivatives containing dithiocarbamate/xanthate groups through ring opening of an α,β-unsaturated γ-sultone with dithiocarbamic acid salts or xanthates prepared in situ. Treatment of the primary products with hydrochloric acid afforded the corresponding β-chloro-γ-(dithiocarbamato)propanesulfonic acids in excellent yields.

Key words

dithiocarbamates - sultones - xanthates - sulfonic acids - nucleophilic substitution - propene sultone

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Referenzen

References and Notes
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51 3-{[(Amino)carbonothioyl]sulfanyl}prop-1-ene-1-sulfonates 2a–l; General Procedure The appropriate secondary amine (0.5 mmol, 1 equiv) and CS₂ (2 mmol, 4 equiv) were added to a solution of K₃PO₄ (0.525 mmol, 1.05 equiv) in H₂O (3 mL) at 0 °C, and the mixture was stirred at rt for 30 min. Sultone 1 (0.5 mmol, 1 equiv) was then added, and stirring was continued at rt for 4 h. The solvent was removed under vacuum and the remaining solid was stirred with MeOH and filtered. The filtrate was evaporated under reduced pressure to give the product. If needed, further purification was carried out by crystallization from the minimum amount of MeOH or by washing the precipitate with Et₂O. Potassium (1Z)-3-{[(Dimethylamino)carbonothioyl]sulfanyl}prop-1-ene-1-sulfonate (2a) White solid; yield: 129 mg (93%); mp 222 °C (dec.). ¹H NMR (400 MHz, D₂O): δ = 6.33 (dt, J = 11.1, 1.4 Hz, 1 H), 6.14 (dt, J = 11.1, 7.7 Hz, 1 H), 4.31 (dd, J = 7.8, 1.3 Hz, 2 H), 3.45 (s, 3 H), 3.32 (s, 3 H). ¹³C NMR (400 MHz, D₂O): δ = 195.8, 134.5, 132.1, 45.5, 41.9, 33.3. HRMS (ESI^–): m/z [M – K]^– calcd for C₆H₁₀O₃NS₃: 239.9828; found: 239.9826.

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