Book chapter
English

3.20 Nitrogen- and Sulfur-Based Stevens and Related Rearrangements

Published inKnochel, P. & Molander, G. A. (Ed.), Comprehensive Organic Synthesis (Second Edition), p. 992-1037
PublisherElsevier
Edition2nd ed.
Publication date2014
Abstract

Stevens and related rearrangements are reactions that involve the formation of ammonium, sulfonium, and oxonium ylide intermediates and then migrations of activated alkyl groups from the onium heteroatoms to the nucleophilic ylide carbons. After a section detailing possible mechanisms, this review will survey the recent advances that have occurred in the last twenty years in the fields of [1,2]-Stevens, [2,3]-Stevens, and Sommelet–Hauser rearrangements of ammonium and sulfonium ylides.

Keywords
  • Ammonium ylide
  • Diazo compound
  • Diradical mechanism
  • Doyle-Kirmse
  • Rearrangements
  • Sommelet–Hauser
  • Stevens
  • Sulfonium ylide
  • Transfer of chirality
Citation (ISO format)
BACH, Renaud, HARTHONG, Steven, LACOUR, Jérôme. 3.20 Nitrogen- and Sulfur-Based Stevens and Related Rearrangements. In: Comprehensive Organic Synthesis (Second Edition). Knochel, P. & Molander, G. A. (Ed.). [s.l.] : Elsevier, 2014. p. 992–1037. doi: 10.1016/b978-0-08-097742-3.00326-8
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Book chapter (Published version)
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Identifiers
ISBN978-0-08-097742-3
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