Please note that the content of this book primarily consists of articles available from Wikipedia or other free sources online. The Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an -acyloxy–thioether in the presence of acetic anhydride. In this reaction, sulfur is reduced while adjacent carbon is oxidized. Several reviews have been published. The usage of -acyl sulfoxides and Lewis acids, such as TiCl4 and SnCl4, allow the reaction to proceed at lower temperatures (0 °C). Common activators besides acetic anhydride are trifluoroacetic anhydride and trifluoromethanesulfonic anhydride. Common nucleophiles besides acetates are arenes, alkenes, amides, and phenols. The mechanism of the Pummerer rearrangement begins with the acylation of the sulfoxide (1 and 2). Compound 3 undergoes elimination to produce the thionium ion 4. Acetate adds to the sulfonium ion to give the final product 5.

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