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Synlett 2018; 29(02): 199-202
DOI: 10.1055/s-0036-1588575
DOI: 10.1055/s-0036-1588575
letter
Oxidation of Organosulfides to Organosulfones with Trifluoromethyl 3-Oxo-1λ3,2-benziodoxole-1(3H)-carboxylate as an Oxidant
Further Information
Publication History
Received: 02 August 2017
Accepted after revision: 29 August 2017
Publication Date:
21 September 2017 (online)
Abstract
An alternative approach is described for the oxidation of organosulfides to the corresponding organosulfones by using trifluoromethyl 3-oxo-1λ3,2-benziodoxole-1(3H)-carboxylate as an oxidant. The oxidation of the sulfides was performed by using 2.4 equivalents of the oxidant in refluxing acetonitrile. The oxidation products were isolated in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588575.
- Supporting Information
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- 31 Sulfones 10a–h; General Procedure A mixture of the appropriate sulfide 9 (0.5 mmol) and benziodoxole 8 (413 mg, 2.4 equiv) in MeCN (3 mL) was refluxed for 16–20 h. When the reaction was complete (TLC), sat. aq NaHCO3 (5 mL) was added and the mixture was extracted with EtOAc (3 × 15 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated under vacuum. The crude product was purified by column chromatography [silica gel, EtOAc–hexane (1:3)]. tert-Butyl Phenyl Sulfone (10a) 22b White solid; yield: 84 mg (0.42 mmol, 85%); mp; 90–92 °C. IR (film): 697, 725, 749, 764, 802, 996, 1021, 1076, 1130, 1277, 1294, 1449, 1475 cm–1. 1H NMR (400 MHz, CDCl3): δ = 1.23 (s, 9 H, t-Bu), 7.46 (t, J = 7.6 Hz, 2 H, ArH), 7.56 (t, J = 7.6 Hz, 1 H, ArH), 7.77 (d, J = 7.6 Hz, 2 H, ArH). 13C NMR (100 MHz, CDCl3): δ = 23.5, 59.7, 128.7, 130.3, 133.6, 135.2. GC/MS: m/z (%) = 198(5), 143(25), 79(13), 77(50), 58(29), 57(100), 51(51), 41(50).
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