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ChemInform Abstract: Reactions of Sulfoxides with Magnesium Amides. Transformation of Sulfoxides into Sulfides, Dithioacetals, and Vinyl Sulfides
- Source :
- ChemInform. 26
- Publication Year :
- 2010
- Publisher :
- Wiley, 2010.
-
Abstract
- The reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and secondary amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined. Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42—52% yields. Sulfoxides bearing hydrogens at the α-positon only (RSOCH2R1) reacted with the tetramethylpiperidinomagnesium reagent at room temperature to produce the corresponding dithioacetals (RSCHR1SR) in 47—86% yields. The treatment of sulfoxides bearing hydrogens both at the α- and β-positions (RSOCHR1CHR2R3) with the magnesium amides at room temperature afforded the corresponding vinyl sulfides (RSCR1=CR2R3) in 52—72% yields accompanying 2.3—27% yields of the corresponding dithioacetals. The pathways leading to the products involving the formation of the sulfur-stabilized carbonium ion intermediates are discussed.
Details
- ISSN :
- 09317597
- Volume :
- 26
- Database :
- OpenAIRE
- Journal :
- ChemInform
- Accession number :
- edsair.doi...........e87d7666da8dac062aa078f6857498b0