24053-87-0Relevant academic research and scientific papers
Hydrolysis of N-phenylalkanesulfinamides in aqueous mineral acids
Datta, Mrityunjoy,Buglass, Alan J.,Tillett, John G.
, p. 565 - 573 (2011)
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.
