Efficient Synthesis of 1-Substituted-5-Hydroxymethylimidazole Derivatives:  Clean Oxidative Cleavage of 2-Mercapto Group¹

Abstract

1-Substituted-5-hydroxymethylimidazoles were prepared through green desulfurization of their 2-mercapto derivatives by the treatment of 30% hydrogen peroxide in the presence of a catalytic amount of transition metal catalysts.

Cytochrome cCatalyzes the Hydrogen Peroxide‐Assisted Oxidative Desulfuration of 2‐Thiouridines in Transfer RNAs

“…This cyclic process repeats to deliver Y and Z . The literature data suggest that Y ‐ and Z ‐type intermediates can be converted into either CH or C=O products . In our case, the formation of H2U, probably by release of hydrogen sulfite (HSO 3 − ) or hydrogen sulfate (HSO 4 − ) from intermediate(s) Y and/or Z , is a predominant stabilization pathway .…”

Oxidative Desulfurization of Azole‐2‐thiones with Benzoyl Peroxide: Syntheses of Ionic Liquids and Other Azolium Salts

“…Regarding the latter, similar systems have been ionized with trityl tetrafluoroborate,43 which releases triphenylmethane and would avoid the inorganic contamination possible by other conceivable routes. Oxidative desulfurizations of compounds 1 to imidazolium salts with hydrogen peroxide and an acid,44–47 iron(III) chloride,48 and nitric acid49–51 are well known 52. Some of Wanzlick's approaches to stable carbenes more than 30 years ago proceeded through oxidations of compounds of type 1 35.…”

From P‐Functional Thiazol‐2‐thione Derivatives to Phosphaalkenes

“…Elemental analyses were done using a Vario EL gas chromatograph. The X‐ray analyses were performed on a Bruker X8‐KappaApexII or Bruker D8‐Venture diffractometer equipped with a low‐temperature device The structures were solved by direct methods refined by full‐matrix least‐squares technique in anisotropic approximation for non‐hydrogen atoms using SHELXS97 and other program packages.…”