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Synthesis and photooxygenation of 3-(p-substituted phenyl)-3a,8a-dihydro-4H-cyclohepta[ d]isoxazoles: facial selectivity.
- Source :
-
Turkish Journal of Chemistry . 2024, Vol. 48 Issue 4, p691-700. 23p. - Publication Year :
- 2024
-
Abstract
- Two 3-(p-substituted phenyl)-3a,8a-dihydro-4H-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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 13000527
- Volume :
- 48
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Turkish Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 179314330
- Full Text :
- https://doi.org/10.55730/1300-0527.3688