1,2-sulfur migrations

Anna W. Sromek, Vladimir Gevorgyan

Research output: Chapter in Book/Report/Conference proceedingChapter

34 Scopus citations

Abstract

1,2-Thio migration has emerged as a valuable synthetic tool for organic chemists. The most common route of 1,2-thio migration proceeds through a thiiranium intermediate. The latter usually proceeds stereoselectively, since substitution of a vicinal leaving group of sulfur takes place with good stereocontrol; substitution or elimination to open the thiiranium ring also proceeds stereoselectively. This and other types of 1,2-thio migration, including 1,2-thio shifts, formal 1,2-thio migration through fragmentation-recombination, [1,5] thio migration in five-membered ring systems, and radical 1,2-thio migrations are discussed in this review.

Original languageEnglish (US)
Title of host publicationSulfur-Mediated Rearrangements I
Pages77-124
Number of pages48
DOIs
StatePublished - Dec 1 2007

Publication series

NameTopics in Current Chemistry
Volume274
ISSN (Print)0340-1022

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Keywords

  • Carbohydrates
  • Heterocycles
  • Morin rearrangement
  • Sulfur migration
  • Thiiranium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Sromek, A. W., & Gevorgyan, V. (2007). 1,2-sulfur migrations. In Sulfur-Mediated Rearrangements I (pp. 77-124). (Topics in Current Chemistry; Vol. 274). https://doi.org/10.1007/128-057