29099-08-9Relevant articles and documents
Hydrolysis of N-phenylalkanesulfinamides in aqueous mineral acids
Datta, Mrityunjoy,Buglass, Alan J.,Tillett, John G.
experimental part, p. 565 - 573 (2011/05/15)
The acid-catalyzed hydrolysis of N-phenylalkanesulfinamides (RSONHPh; 1, R = iPr; 2, R = tBu; 3, R = 1-adamantyl) has been studied in aqueous mineral acids. Hydrolysis was found to proceed via a slow spontaneous (uncatalyzed) pathway, an A-2 (bimolecular) acid-catalysis pathway, and an acid-dependent nucleophilic catalysis pathway, the last of which predominates in hydrobromic and hydrochloric acid solutions. A mechanistic switch over from A-2 to A-1 was detected for compounds 2 and 3 in concentrated sulfuric acid. Order of catalytic activity, effect of added salts, Arrhenius parameters, kinetic solvent isotope, and solvent effects are all consistent with the proposed mechanisms. Copyright Taylor & Francis Group, LLC.
Electro-oxidative Neutral Deprotection of S-t-Butyl Thioates to give Carboxylic Acids
Kimura, Makoto,Matsubara, Shinichi,Sawaki, Yasuhiko
, p. 1619 - 1620 (2007/10/02)
t-Butyl thioates are proposed as a convenient protecting group for carboxylic acids, because their deprotection under neutral conditions can be attained by electro-oxidation using bromide salts as electrolytes in aqueous acetonitrile.