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Turkish Journal of Chemistry

Author ORCID Identifier

MAHİRE OLGUN: 0009-0001-5311-6459

ABDULLAH MENZEK: 0000-0001-6177-7532

ERTAN ŞAHİN: 0000-0002-6311-8917

YASİN ÇETİNKAYA: 0000-0001-6617-5055

DOI

10.55730/1300-0527.3688

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.

Keywords

Diels-Alder reactionfacial selectivityisoxazolephotooxygenationdensity functional theory

First Page

691

Last Page

700

Creative Commons License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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