Thionyl Chloride-Mediated One-Pot <i>O</i>‑, <i>N</i>‑, and <i>S</i>‑Deacetylation and Esterification of a Diverse Series of Acetoxy, Acetamido, and Thioacetate Carboxylic Acids.

ABSTRACT: Thionyl chloride (SOCl₂) has been extensively used as a chlorinating reagent for the esterification of carboxylic acids via the formation of an acid chloride intermediate. While SOCl₂-mediated deacetylation of acetoxy (O-deacetylation) and acetamido (N-deacetylation) esters is rare and has been reported on a coumarin substrate, deacetylation of thioacetate (S-deacetylation) esters by SOCl₂ is unknown. Furthermore, a simultaneous deacetylation and esterification of acetoxy, acetamido, and thioacetate carboxylic acids in a one-pot synthetic scheme has not been reported in the literature. We report deacetylation and esterification of a diverse series of acetoxy carboxylic acids mediated by SOCl_2, with examples from acetamido and

SUBMITTER: Khaliq T 

PROVIDER: S-EPMC12917795 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature