dc.contributor.author | Coşkun, Necdet | |
dc.contributor.author | Asutay, Oktay | |
dc.date.accessioned | 2022-05-11T14:47:08Z | |
dc.date.available | 2022-05-11T14:47:08Z | |
dc.date.issued | 2007 | |
dc.identifier.issn | 0040-4039 | |
dc.identifier.uri | https://doi.org/10.1016/j.tetlet.2007.05.058 | |
dc.identifier.uri | https://hdl.handle.net/20.500.11776/10439 | |
dc.description.abstract | Imidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | Pergamon-Elsevier Science Ltd | en_US |
dc.identifier.doi | 10.1016/j.tetlet.2007.05.058 | |
dc.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | nitrones | en_US |
dc.subject | rearrangement | en_US |
dc.subject | imidazoline | en_US |
dc.subject | imidazoline-3-oxides | en_US |
dc.subject | ring-chain tautomers | en_US |
dc.subject | Conversion | en_US |
dc.title | Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring-chain tautomerism | en_US |
dc.type | article | en_US |
dc.relation.ispartof | Tetrahedron Letters | en_US |
dc.department | Meslek Yüksekokulları, Muratlı Meslek Yüksekokulu, Kimya ve Kimyasal İşleme Teknolojileri Bölümü | en_US |
dc.identifier.volume | 48 | en_US |
dc.identifier.issue | 29 | en_US |
dc.identifier.startpage | 5151 | en_US |
dc.identifier.endpage | 5155 | en_US |
dc.institutionauthor | Asutay, Oktay | |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.authorscopusid | 7004177880 | |
dc.authorscopusid | 35080000800 | |
dc.identifier.wos | WOS:000247995900043 | en_US |
dc.identifier.scopus | 2-s2.0-34250325972 | en_US |