Chemoselective cyclodesulfurization <i>vs.</i> dehydration enabled by aqueous microdroplet chemistry.

ABSTRACT: Dehydration reactions are typically favored in microdroplets due to the relatively dry environment at the air-water interface. However, we demonstrate that cyclodesulfurization may outcompete dehydration under these conditions. We report on a catalyst-free method for inducing a two-step cyclodesulfurization in microdroplets under ambient conditions by reacting benzhydrazide with phenyl isothiocyanate. The reaction involves the formation of benzhydrazine-1-carbothioamide, a compound that contains two nucleophilic centers. During competing nucleophilic attacks by hydroxyl and thiol groups, reactive oxygen species at the droplet interface oxidize the thiol, forming the sulfoxylic and then the sulfurous acid. These transient reactive intermediates are detected using online mass spectrometry. T

SUBMITTER: Jana M 

PROVIDER: S-EPMC12498146 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature