Synthesis and photooxygenation of 3-( p -substituted phenyl)-3a,8a-dihydro- 4H -cyclohepta[d]isoxazoles: facial selectivity.
| Autor: | Olgun ME; Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkiye., Menzek A; Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkiye.; Department of Emergency Aid and Disaster Management, Faculty of Health Sciences, Ardahan University, Ardahan, Turkiye., Şahin E; Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkiye., Çetinkaya Y; Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkiye. |
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| Jazyk: | angličtina |
| Zdroj: | Turkish journal of chemistry [Turk J Chem] 2024 May 28; Vol. 48 (4), pp. 691-700. Date of Electronic Publication: 2024 May 28 (Print Publication: 2024). |
| DOI: | 10.55730/1300-0527.3688 |
| Abstrakt: | Two 3-( p -substituted phenyl)-3a,8a-dihydro-4 H -cyclohepta[d]isoxazoles were synthesized by 1,3-dipolar cycloaddition of the corresponding nitrile oxides with cycloheptatriene. Two endoperoxides were synthesized as facially selective and single products in high yields (93%-95%) from the reactions of isoxazole derivatives with singlet oxygen. The exact configurations of the endoperoxide with a methyl group in the phenyl ring and the diol synthesized from it were confirmed by X-ray analysis. To elucidate the mechanism, the formation energy of the endoperoxide was investigated by simulations using the software package Gaussian 09 and density functional theory calculations via the M06-2X/6-311+G(d,p) level method in dichloromethane. The results were consistent with experimental findings showing the formation of isoxazole products. (© TÜBİTAK.) |
| Databáze: | MEDLINE |
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