90909-32-3Relevant academic research and scientific papers
PUMMERER REARRANGEMENTS USING CHLOROTRIMETHYLSILANE
Lane, Simon,Quick, Stephen J.,Taylor, Richard J. K.
, p. 1039 - 1042 (2007/10/02)
Pummerer rearrangements of 3-carbomethoxythian-4-one S-oxide (1) have been investigated and chlorotrimethylsilane found to be the reagent of choice for preparing the corresponding α,β-unsaturated sulphides (2 and 3).Related chlorotrimethylsilane-induced Pummerer rearrangements are also reported.
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.
