Synthesis and photooxygenation of 3-(<i>p</i>- substituted phenyl)-3a,8a-dihydro-<i>4H</i>- cyclohepta[d]isoxazoles: facial selectivity
Olgun, Mahireire Emel, Menzek, Abdullah, Sahin, Ertan, Cetinkaya, Yasin
Two 3-(p p-substituted phenyl)-3a,8a-dihydro-4H-cyclohepta[d]isoxazoles 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 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.
- Journal
- TURKISH JOURNAL OF CHEMISTRY
- Year
- 2024
- Volume
- 48
- Issue
- 4
- ISSN
- 1300-0527
- DOI
- 10.55730/1300-0527.3688
- WoS UID
- WOS:001314807000012