121824-39-3Relevant academic research and scientific papers
Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals
Ielo, Laura,Pillari, Veronica,Miele, Margherita,Holzer, Wolfgang,Pace, Vittorio
, p. 5444 - 5449 (2020)
A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alcoholic groups [(hetero)-aromatic, aliphatic] offer a convenient access to the title compounds. Genuine chemoselectivity is uniformly observed in the case of multi-functionalized systems. (Figure presented.).
Syntheses of Sulfinylmethyl Ethers and Conversion of these into Halomethyl and Acyloxymethyl Ethers
Antonsen, Oeyvind,Benneche, Tore,Undheim, Kjell
, p. 515 - 523 (2007/10/02)
Halomethyl ethers can be prepared from sulfinyl ethers by cleavage of the carbon-sulfur bond with thionyl chloride, acetyl chloride or trimethylsilyl halides.In the presence of alkenyl groups in the substrate, acetyl chloride is the reagent of choice.Trifluoroacetic anhydride reacts in the same manner to form the trifluoroacetoxymethyl ether.With acetic anhydride, catalysis by methanesulfonic acid was required.At elevated temperatures in the presence of sodium acetate the products were formed by the Pummerer rearrangement.
