55085-94-4Relevant academic research and scientific papers
Substituted propargylic sulfoxides: synthesis and -sigmatropic rearrangement in the presence of thiophilic reagents
Baudin, J. B.,Julia, S. A.,Lorne, R.
, p. 440 - 456 (2007/10/02)
The allenic sulfoxides 2 and 12 were converted into the substituted propargylic sulfoxides 3 and 13, respectively, by deprotonation with methyl lithium and reaction with electrophilic reagents.Smooth thermal -sigmatropic rearrangement of 3 and 13, using 2-mercapto-1-methylimidazole to desulfurize the intermediate allenic sulfenate XVa, yielded the corresponding conjugated enones 10.The possible reaction mechanism for these two transformations were examined. Key words: Allenic sulfoxides; propargylic sulfoxides; organolithium compounds adjacent to sulfoxides; -sigmatropic rearrangement; desulfurization; α,β-unsaturated enones; furanes.
