Asutay, OktayCoşkun, Necdet2022-05-112022-05-1120100026-92471434-4475https://doi.org/10.1007/s00706-010-0344-yhttps://hdl.handle.net/20.500.11776/10440C-2-unsubstituted imidazoline-3-oxides were reduced with NaBH4 in THF to give the corresponding trans-3,5-diarylimidazolidin-1-ols, while under the same conditions C-2-substituted derivatives gave the corresponding ring-chain-ring tautomers. Treatment of the crude reaction mixture from the reduction of C-2-unsubstituted imidazoline-3-oxides with a MeOH-H2O mixture provided reductive C-N bond cleavage to give hydroxylamines, while under the same conditions ring-chain-ring tautomers remained unchanged.en10.1007/s00706-010-0344-yinfo:eu-repo/semantics/closedAccessNitronesRearrangementRing-chain-ring tautomersSelectivityHydroxylamineFree-RadicalsNitronesChemistryArticle1418901905Q2WOS:0002808028000112-s2.0-78149414020Q3