80563-97-9Relevant academic research and scientific papers
Preparative Aspects of 1,3-Dithiolanes Synthesizable from β-Dicarbonyl Compounds
Stahl, Ingfried,Schramm, Berthold,Manske, Rainer,Gosselck, Juergen
, p. 1158 - 1172 (2007/10/02)
The reaction of 1,2-ethanedithiol (1) with the β-dicarbonyl compounds 2 leads to the 1,3-dithiolanes 3 which are accessible to regioselective reactions at the free carbonyl function.Thus the derivatives of the β-keto acid esters can be hydrolyzed to give the corresponding carboxylic acids 4 which make the ester group modified 1,3-dithiolanes 3 accessible in good yields.Addition of trimethyloxonium tetrafluoroborate produces the monodithiolanium salts 6 which on hydrolysis rapidly decompose into 2 and the vinyl thioethers 8.Reaction of 3 with Grignard reagents 10 yields the 2-(2-hydroxyalkyl)-1,3-dithiolanes 11.Dethioacetalization of 11 with HgO/BF3 leads to the β-hydroxy ketones 12.The retro reaction of 3 leads to the basic compounds 2 which, however, are obtained only in moderate yields. - Finally the performance of the sensitive silylenol ether 13 starting from 3g is described.
The Reaction of 2-Ethoxy-1,3-oxathiolane with Carbonyl Compounds in the Presence of ZnCl2 or HgCl2
Tanimoto, Shigeo,Jo, Shigeo,Sugimoto, Toyonari,Okano, Masaya
, p. 3237 - 3238 (2007/10/02)
In the reaction of 2-ethoxy-1,3-oxathiolane with carbonyl compounds in the presence of ZnCl2 or HgCl2, it has been found that only the breaking of the endocyclic bond (C-O or C-S bond) occurs, while the breaking of the exocyclic C-O bond to give the 1,3-o
