221288-76-2Relevant academic research and scientific papers
Oxidation of α-sulfonyl selenides: Formation of selenolesters
Yi, Jae Sang,Kim, Kyongtae
, p. 71 - 76 (2007/10/03)
Treatment of 7-phenylseleno-7,12-dihydrobenzo[5,6][1,3]thiazepino[3,2-a]benzimidazole 6,6-dioxide 7a in CH2Cl2 with m-chloroperbenzoic acid (MCPBA) and 28% H2O2 at room temperature gave Se-phenyl 2-[(benzimidazol-l-yl)methyl]selenobenzoate 8a. Similarly, the oxidation of sulfone 7a in THF with aqueous Oxone7 at room temperature gave the same selenolester 8a. The formation of selenolesters 8 can be explained by assuming either the involvement of oxaseleniranium cation 13, having a sulfinate group at C-2 of the benzimidazole moiety, as an intermediate which is believed to be formed by an intramolecular nucleophilic attack of the polarized oxygen of the Se=O bond of selenoxide 6 to the α-carbon next to the sulfonyl group, or Pummerer-type reactions.
