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Study of the substituent-influenced anomeric effect in the ring-chain tautomerism of 1-alkyl-3-aryl-naphth[1,2- e][1,3]oxazines

  • The stabilities of the trans (B) and cis (C) tautomeric ring forms that are experimentally observed in the ring- chain tautomeric interconversion of 1-alkyl-3-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines has been investigated. Stability differences are explained by the analysis of the natural bond orbital results for the lone pairs of electrons that are on the heteroatoms in the oxazine ring system and by regression analysis of the calculated 13C NMR chemical shift values.

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Author:Istvan Szatmari, Diana Toth, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, Ferenc Fülöp
Document Type:Article
Year of first Publication:2006
Year of Completion:2006
Release Date:2017/03/25
Source:European journal of organic chemistry. - (2006), 20, S. 4670 - 4675
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert