Abstract
The Stevens and related rearrangements of X-onium ylides (X = heteroatom) convert a readily accessible heteroatom–carbon (X–C) bond into a new carbon–carbon (C–C) bond. Previous studies on the rearrangements have been performed mainly using ammonium-(N) and sulfonium-(S) ylides, as the title indicates, next to oxonium-(O) ylides. Although previous examples are limited, the rearrangements of selenium-(Se) and halonium-(I, Br, Cl) ylides have been studied. The related rearrangements are the Sommelet–Hauser rearrangement and the Doyle–Kirmse reaction. The Doyle–Kirmse reaction is categorized as a Stevens rearrangement. This review is an update of the second edition of Comprehensive Organic Synthesis, which was published in 2014, and is being published for the volume titled “Carbon single bond Carbon Bond Formation.” In this review, recent examples of these rearrangements are surveyed, including the Stevens rearrangement reported from approximately 2012 to 2022 and the S–H rearrangement reported from approximately 2008 to 2022.
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