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Brøndsted Nielsen, M. et al.: 2014 Science of Synthesis, 2014/2: Knowledge Updates 2014/2 DOI: 10.1055/sos-SD-127-00361
Knowledge Updates 2014/2

27.4.3 Thioaldehyde and Thioketone S-Oxides and S-Imides (Sulfines and Derivatives) (Update 2014)

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Editors: Brøndsted Nielsen, M.; Krause, N.; Marek, I.; Schaumann, E.; Wirth, T.

Authors: Aguilar, E.; Beier, P.; Fuchibe, K.; Ghorai, S.; Heimgartner, H.; Ibis, C.; Ichikawa, J.; Lipshutz, B. H.; Liu, Q.; López, L. A.; Margaretha, P.; Mlostoń, G.; Shneider, O. S.; Szpilman, A. M.; Vilhelmsen, M. H.; Yin, Q.; You, S.-L.

Title: Knowledge Updates 2014/2

Print ISBN: 9783131762412; Online ISBN: 9783131975010; Book DOI: 10.1055/b-003-125812

1st edition © 2014 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods of synthesis and new applications for thiocarbonyl S-oxides (sulfines) and thiocarbonyl S-imides. In general, thiocarbonyl S-oxides are more stable and in many instances can be isolated. The in situ generated thiocarbonyl S-imides are efficient “sulfur-transfer agents” via the isomeric thiaziridines, formed as products of electrocyclic ring closure. Stable thiocarbonyl S-imides, derived from hexafluorothioacetone, are useful 1,3-dipoles and are applied in the preparation of fluorinated five-membered heterocycles.

Key words

thiazolidines - cycloaddition - five-membered rings - oxidation - small-ring systems - thiones
 
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