CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0117-0120
DOI: 10.1055/s-0036-1588573
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Rapid Transformation of Alkyl Halides into Symmetrical Disulfides Using Sodium Sulfide and Carbon Disulfide

Ishani Bhaumik, Anup Kumar Misra*
  • Division of Molecular Medicine, Bose Institute, P-1/12, C. I. T. Scheme VII M, Kolkata 700054, India   Email: akmisra69@gmail.com
Further Information

Publication History

Received: 06 June 2017

Accepted after revision: 29 August 2017

Publication Date:
14 September 2017 (online)

Abstract

An efficient one-pot reaction has been developed for the preparation of symmetrical disulfide derivatives directly from alkyl halides by reaction with a combination of sodium sulfide and carbon disulfide without requirement for any catalyst.

 
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  • 23 Typical experimental procedure for the preparation of symmetrical dialkyl disulfides: To a solution of Na2S·9H2O (1.0 mmol) in DMF (2 mL) was added CS2 (1.0 mmol) at room temperature. The alkyl halide (1.0 mmol) was added to the dark-red reaction mixture at room temperature with vigorous stirring. The color of the reaction mixture changed from red to yellow. The reaction mixture was stirred for the appropriate time (Table 2), then poured into water and extracted with Et2O (2 × 25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified over SiO2 using hexane–EtOAc (15:1) as eluant to give the pure dialkyl disulfide derivative (Table 2)
  • 24 Spectroscopic data of novel products:Di[2-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)ethyl] Disulfide (11): Yield: 733 mg (90%); Colorless oil; 1H NMR (500 MHz, CDCl3): δ = 5.18 (t, J = 7.5 Hz, 2 H), 5.08 (t, J = 9.5 Hz, 2 H), 4.97 (m, 2 H), 4.55 (d, J = 9.0 Hz, 2 H), 4.26 (dd, J = 4.5, 8.0 Hz, 2 H), 4.14–3.95 (m, 4 H), 3.89–3.60 (m, 4 H), 2.96–2.71 (m, 4 H), 2.09, 2.06, 2.02, 2.00 (4 × s, 24 H); 13C NMR (125 MHz, CDCl3): δ = 170.2 (2 C), 169.9 (2 C), 169.0 (2 C), 168.9 (2 C), 100.7 (2 C), 72.7 (2 C), 72.6 (2 C), 71.8 (2 C), 69.6 (4 C), 67.6 (2 C), 61.7 (2 C), 38.3 (2 C), 20.5 (8 C); HRMS (ESI): m/z [M+Na]+ calcd. for C32H46O20S2: 837.1922; found: 837.1916.Di[2-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)ethyl] Disulfide (12): Yield: 700 mg (86%); Colorless oil; 1H NMR (500 MHz, CDCl3): δ = 5.39-5.31 (m, 2 H), 5.20–5.13 (m, 2 H), 5.05–4.95 (m, 2 H), 4.50 (d, J = 8.0 Hz, 2 H), 4.19–4.09 (m, 4 H), 4.05–3.89 (m, 2 H), 3.81–3.61 (m, 2 H), 2.91–2.71 (m, 4 H), 2.16, 2.07, 2.05, 1.98 (4 × s, 24 H); 13C NMR (125 MHz, CDCl3): δ = 170.1 (2 C), 170.0 (2 C), 169.9 (2 C), 169.2 (2 C), 101.4 (2 C), 70.8 (4 C), 70.7 (2 C), 68.7 (4 C), 66.9 (2 C), 61.1 (2 C), 20.7 (8 C); HRMS (ESI): m/z [M+Na]+ calcd. for C32H46O20S2: 837.1922; found: 837.1917.Di-[2-O-(2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl)ethyl] Disulfide (13): Yield: 594 mg (85%); Colorless oil; 1H NMR (500 MHz, CDCl3): δ = 5.31–5.19 (m, 4 H), 5.05 (t, J = 9.5 Hz, 2 H), 4.76 (s, 2 H), 3.98–3.88 (m, 2 H), 3.85–3.69 (m, 4 H), 2.98–2.81 (m, 4 H), 2.15, 2.08, 1.98 (3 × s, 18 H), 1.22 (d, J = 6.0 Hz, 6 H); 13C NMR (125 MHz, CDCl3): δ = 169.9 (2 C), 169.8 (2 C), 169.7 (2 C), 97.5 (2 C), 70.9 (2 C), 70.6 (2 C), 69.7 (2 C), 69.0 (2 C), 66.6 (2 C), 66.3 (2 C), 38.2 (2 C), 20.8 (6 C), 17.4 (2 C); HRMS (ESI): m/z [M+Na]+ calcd. for C28H42O16S2: 721.1812; found: 721.1806