99172-76-6Relevant articles and documents
Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways
Li, Xin,Carter, Rich G.
supporting information, p. 5541 - 5545 (2018/09/25)
Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Br?nsted-enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.
Synthesis of 2-thioaldoses via BF3-promoted cycloaddition of β-methoxyvinyl sulfides with 2,3-O-isopropylidene derivatives of aldehydo-aldoses
Sugimura, Hideyuki,Kusakabe, Kousuke
, p. 69 - 72 (2013/02/23)
A highly stereoselective approach to the synthesis of 2-thioaldose derivatives via BF3-promoted cycloaddition of β-methoxyvinyl sulfides with 2,3-O-isopropylidene derivatives of aldehydo-aldoses is described. Georg Thieme Verlag Stuttgart · New
Ionic liquid as catalyst and reaction medium: A simple, convenient and green procedure for the synthesis of thioethers, thioesters and dithianes using an inexpensive ionic liquid, [pmIm]Br
Ranu, Brindaban C.,Jana, Ranjan
, p. 1811 - 1818 (2007/10/03)
An easily accessible and inexpensive room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes the reaction of alkyl halides or acyl halides with thiols without any solvent at room temperature leading to the synthesis of thioethers and thioesters in high yields. This reaction has also been extended for the preparation of dithianes and transthioetherification. The ionic liquid is recovered and recycled for subsequent runs.