Anionic Organosulfur Compounds in Synthesis: New Applications of the Ramberg-Bäcklund Reaction

  • Eric Block
  • David Putman
  • Adrian Schwan
Part of the NATO ASI Series book series (NSSA, volume 197)


Organosulfur carbanions derived from saturated and unsaturated sulfides, sulfoxides and sulfones, from dithioacetals (e.g. 1,3-dithiane) and trithioformates ((RS)3CH), from sulfinate and sulfonate esters, as well as from other sulfur-containing systems may undergo the entire gamut of reactions characteristic of organometallic compounds.1 A partial list of such reactions would include protonation/deuteration, carbonation, inter- and intramolecular alkylation, hydroxyalkylation with epoxides (nucleophilic ring opening) and with aldehydes and ketones (carbonyl addition), acylation with carboxylic acid derivatives, addition to carbon-carbon and carbon-nitrogen multiple bonds (including conjugate addition), elimination and fragmentation, oxidative coupling, and rearrangement. In addition to their ease of preparation and versatile chemistry, organosulfur carbanions have been widely and artfully used in organic synthesis because of the diverse possibilities for further functionalization of the primary products as well as removal of sulfur through elimination, reduction, or hydrolysis.1


Organosulfur Compound Sulfonyl Group Propargyl Alcohol Allylic Sulfone Nucleophilic Ring Opening 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Eric Block
    • 1
  • David Putman
    • 1
  • Adrian Schwan
    • 1
  1. 1.Department of ChemistryState University of New York at AlbanyAlbanyUSA

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