95066-05-0Relevant academic research and scientific papers
Pummerer Rearrangements Using Chlorotrimethylsilane
Lane, Simon,Quick, Stephen J.,Taylor, Richard J. K.
, p. 2549 - 2552 (2007/10/02)
Attempted Pummerer rearrangement of 3-methoxycarbonylthian-4-one S-oxide in refluxing acetic anhydride gives unexpected products in which β-carbon oxidation and ring contraction has taken place.Treatment of 3-methoxycarbonylthian-4-one with N-chlorosuccinimide gives similar rearrngement products.These rearrangements are rationalised by the intermediacy of a common thiiranium ion.Chlorotrimethylsilane in refluxing tetrachloromethane efficiently effects the expected Pummerer rearrangement of 3-methoxycarbonylthian-4-one S-oxide into the corresponding α,β-unsaturated sulphides.Reactions of this reagent with related sulphoxides are also described.
