REACTIONS OF ALDONITRONES (3-IMIDAZOLINE-3-OXIDES) WITH ISOTHIOCYANATES

Article abstract of DOI:10.1007/BF00863378

Cycloaddition of aldonitrones (derivatives of 3-imidazoline-3-oxide) to isothiocyanates depends on the N(1) substituent.Electron donating substituents facilitate cycloaddition to the C=N bond, whereas electron acceptors activate the C=S bond.Hyrolysis of adducts on the C=N bond followed by oxidation gives nitroxide radicals which are pH-sensitive spin probes. Keywords: aldonitrones, 3-imidazoline-3-oxide derivatives, isothiocyanates.