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.
Author details: | Istvan SzatmariORCiD, Diana Toth, Andreas KochORCiDGND, Matthias HeydenreichORCiD, Erich KleinpeterORCiDGND, Ferenc FulopORCiD |
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URL: | http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200600563/pdf |
DOI: | https://doi.org/10.1002/ejoc.200600563 |
Publication type: | Article |
Language: | English |
Year of first publication: | 2006 |
Publication year: | 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 |