61464-29-7Relevant academic research and scientific papers
Reaction of Acetone with Ethyl Mercaptoacetate.
Scrowston, John R.,Scrowston, Richard M.
, p. 214 - 228 (2007/10/02)
Acetone reacts with ethyl mercaptoacetate in the presence of an acid catalyst to give a range of by-products, of which fourteen have been identified, in addition to the expected thioacetal (1).Acetone undergoes self-condensation under the conditions of the reaction.The α,β-unsaturated products undergo conjugate addition of ethyl mercaptoacetate, to give the appropriate ketosulphides ; the thioacetal (5) from the mesityl oxide adduct was also formed.The cyclic hemithioacetal (7) from acetone and ethyl mercaptoacetate was isolated.There is evidence that the thioacetal (1) undergoes thermal decomposition, to give the isopropenyl sulphide (9).It is believed that the monosulphoxide (11) of the thioacetal (1) is formed during the thioacetalisation reaction, and that this then undergoes Pummerer cleavage, to give products (10) and (12).The formation of the cyclic hemithioacetal (13) may be rationalised in terms of a co-oxidation reaction between ethyl mercaptoacetate and the isopropenyl sulphide (9).
