2018
DOI: 10.1039/c8ob00024g
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Thermal conversion of primary alcohols to disulfidesviaxanthate intermediates: an extension to the Chugaev elimination

Abstract: Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially availabl… Show more

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Cited by 13 publications
(3 citation statements)
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“…Further, 2D-COS spectra (all modifications) also revealed that crosslinking process had a high impact on band intensities in the spectral region of 1200 cm -1 to 850 cm -1 (Figure 4B, Figure 4C). In this region, the spectra are primarily shaped by C-O-C stretching ether linkages and pyranose backbone rings and carbon-oxygen bonds (C-OH), indicating presence of primary alcohols (63). The reduction in intensity of bands in this region could be also a consequence of ester bond formation between carboxyl groups of citric acid (CA) and C-OH of anhydrous glucose units in BC fibrils.…”
Section: Analysis Of Atr-ftir Spectra Of Modified Bcmentioning
confidence: 99%
“…Further, 2D-COS spectra (all modifications) also revealed that crosslinking process had a high impact on band intensities in the spectral region of 1200 cm -1 to 850 cm -1 (Figure 4B, Figure 4C). In this region, the spectra are primarily shaped by C-O-C stretching ether linkages and pyranose backbone rings and carbon-oxygen bonds (C-OH), indicating presence of primary alcohols (63). The reduction in intensity of bands in this region could be also a consequence of ester bond formation between carboxyl groups of citric acid (CA) and C-OH of anhydrous glucose units in BC fibrils.…”
Section: Analysis Of Atr-ftir Spectra Of Modified Bcmentioning
confidence: 99%
“…Starting compounds were prepared according to literature procedures: α-(trifluoromethyl)styrenes [17]; potassium phenethyl xanthogenate [18]; potassium n-hexyl xanthogenate [19]; potassium isoamyl xanthogenate [20]; cyclopentyl xanthogenate [20]; potassium cyclohexyl xanthogenate [20]; potassium isopropyl xanthogenate [21]; potassium tert-butyl xanthogenate [22]; 2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile (3DPAFIPN) [11].…”
Section: General Informationmentioning
confidence: 99%
“…In this region, the spectra are primarily shaped by C-O-C stretching ether linkages and pyranose backbone rings and carbon-oxygen bonds (C-OH), indicating presence of primary alcohols [74]. The reduction in intensity of bands in this region could be also a consequence of ester bond formation between carboxyl groups of citric acid (CA) and C-OH of anhydrous glucose units in BC fibrils.…”
Section: Analysis Of Atr-ftir Spectramentioning
confidence: 99%