80437-03-2Relevant academic research and scientific papers
Additions to Alkenes via Metal Ion-Promoted Oxidation of Dialkyl and Diaryl Disulphides
Bewick, Alan,Mellor, John M.,Owton, W. Martin
, p. 1039 - 1044 (2007/10/02)
Reactions of alkenes with di-n-propyl, diphenyl, and dibenzyl disulphide in the presence of lead(IV) salts in trifluoroacetic acid-dichloromethane are described.The products, vicinal trifluoroacetoxysulphides, are obtained in higher yields with manganese(III) salts as the oxidant.Alternative reaction conditions with use of iron(III) salts or in the absence of added metal salts are also described.Trifluoroacetoxysulphides derived from diphenyl disulphide react with acetonitrile under Ritter conditions to give acetamidosulphides but trifluoroacetoxysulphides derived from dibenzyl disulphide only give the vicinal acetamidosulphides in poor yield as a result of an alternative reaction pathway affording benzylacetamide.Conversions of acetamidosulphides into aminosulphides and into acetamidothiols are described.
REACTION OF THIOLSULFINATES WITH TRIHALOACETIC ANHYDRIDES. II. ADDITION OF SULFENYL TRIHALOACETATES TO OLEFINS
Morishita, Tsuyoshi,Furukawa, Naomichi,Oae, Shigeru
, p. 2539 - 2546 (2007/10/02)
Treatment of thiolsulfinates with trifluoro- or trichloroacetic anhydride at -20 deg C in the presence of various olefins in carbon tetrachloride afforded the corresponding β-trifluoro- or trichloroacetoxy sulfides in good yields.The β-trihaloacetoxy sulfides are considered to be resulted by the electrophilic addition of the sulfenyl trihaloacetates, formed as transient intermediates, to olefins.The addition takes place stereospecifically in trans manner and the regioselectivity for the addition with unsymmetrical olefins obeyed the Markownikoff orientation rule, except 3,3-dimethyl-1-butene which gave initially the anti-Markownikoff product 3 due to the steric hindrance, however the adduct 3 is readily converted to the Markownikoff product 22 upon heating.Since the addition is highly regioselective and stereospecific, this is a very convenient procedure for the syntheses of β-trihaloacetoxy sulfides.
