138197-12-3Relevant academic research and scientific papers
1,3-Oxathiolane Synthesis: Spirocyclic 1,3-Oxathiolanes from the Lewis-Acid-Catalyzed Reaction of Cyclic Trithiocarbonates and Oxiranes
Oremus, Vladimir,Linden, Anthony,Heimgartner, Heinz
, p. 1500 - 1510 (2007/10/02)
The cyclic trithiocarbonates 1,3-dithiolane-2-thione (4) and 1,3-dithiole-2-thione (9) in 1,2-dichloroethane and MeCN, respectively, react with alkyl- and phenyl-substituted oxiranes 2 in the presence of Lewis acids to give 1-oxa-4,6,9-trithiaspirononanes 5 and 6 (Scheme 2) and 1-oxa-4,6,9-trithiaspironon-7-enes 10 and 11 (Scheme 3), respectively.The reactions proceed regioselectively yielding 2-alkyl (5, 10) and 3-phenyl-derivatives (6, 11) as the main products.From the reaction of 4 and 2-phenyloxirane (2e) with TiCl4, 2-phenyl-1,4,6,9-tetrathiaspirononane (7) is isolated as a minor product.The molecular structures of 5a, 6e, and 7 are established by X-ray crystallography.
