14035-54-2Relevant articles and documents
FeCl3·6H2O/acetaldehyde, a versatile system for the deprotection of ketals and acetals via a transacetalization process
Schiavo, Lucie,Jeanmart, Lo?c,Lanners, Steve,Choppin, Sabine,Hanquet, Gilles
, p. 1421 - 1424 (2017/02/23)
Mild and efficient catalytic deprotection of ketals/acetals mediated by FeCl3·6H2O/acetaldehyde has been described in this paper. The versatility and high chemoselectivity of the iron(iii)/aldehyde system are demonstrated by a large scope of examples. Deprotected ketones/aldehydes are nearly quantitatively isolated after filtration over a pad of silica gel followed by evaporation of volatile by-products.
Studies on the Preparation and Reactions of Tritylsulfenimines
Branchaud, Bruce P.
, p. 3531 - 3538 (2007/10/02)
Carbonyl compounds react with stable, crystalline triphenylmethanesulfenamide (TrSNH2, 4) under mild conditions to form tritylsulfenimines 5 and 6.Lithiation of acetone tritylsulfenimine (5c) at O deg C led to a novel rearrangement-decomposition producing
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.