Synthesis and photooxygenation of 3-(p-substituted phenyl)-3a,8a-dihydro-4H-cyclohepta[d]isoxazoles: facial selectivity.

IF 1.3 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Turkish Journal of Chemistry Pub Date : 2024-05-28 eCollection Date: 2024-01-01 DOI:10.55730/1300-0527.3688
Mahire Emel Olgun, Abdullah Menzek, Ertan Şahin, Yasin Çetinkaya
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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.

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3-(对取代苯基)-3a,8a-二氢-4H-环庚烷并[d]异恶唑的合成与光氧合:面部选择性。
通过相应的腈氧化物与环庚三烯的 1,3-二极环加成,合成了两种 3-(对取代苯基)-3a,8a-二氢-4H-环庚[d]异噁唑。通过异噁唑衍生物与单线态氧的反应,以高产率(93%-95%)合成了两种内过氧化物,它们都是面选择性的单一产物。通过 X 射线分析,确认了苯基环中带有一个甲基的内过氧化物和由其合成的二元醇的确切构型。为了阐明其机理,研究人员使用高斯 09 软件包进行了模拟,并在二氯甲烷中通过 M06-2X/6-311+G(d,p) 级方法进行了密度泛函理论计算。结果与实验结果一致,显示出异噁唑产物的形成。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Turkish Journal of Chemistry
Turkish Journal of Chemistry 化学-工程:化工
CiteScore
2.40
自引率
7.10%
发文量
87
审稿时长
3 months
期刊介绍: The Turkish Journal of Chemistry is a bimonthly multidisciplinary journal published by the Scientific and Technological Research Council of Turkey (TÜBİTAK). The journal is dedicated to dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, polymeric, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences especially in chemical engineering where molecular aspects are key to the findings. The journal accepts English-language original manuscripts and contribution is open to researchers of all nationalities. The journal publishes refereed original papers, reviews, letters to editor and issues devoted to special fields. All manuscripts are peer-reviewed and electronic processing ensures accurate reproduction of text and data, plus publication times as short as possible.
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