Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans

Islam Md Monarul; Akther Thamina; Ikejiri Yusuke; Matsumoto Taisuke; Tanaka Junji; Rahman Shofiur; Georghiou Paris E.; Hughes David L.; Redshaw Carl; Yamato Takehiko

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Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans

机译：Calix [3]苯并呋喃的合成，结构性能，亲电子取代反应和DFT计算研究

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Calix[3]benzofurans have been synthesized by a modified TosMIC coupling reaction, followed by acid treatment and an intramolecular cyclization reaction with TMSI (trimethylsilyl iodide); X-ray analysis established the structures of two samples, both showing a cone conformation. H-1 NMR spectroscopic analyses of the calix[3]benzofurans reveal that they can adopt drastically different conformations in solution and undergo very fast conformational changes relative to the NMR time scale. Calix[3]benzofuran 4a exists as two conformers, namely the cone and saddle forms, in a ratio of 83 : 17 at -50 degrees C. A series of calix[3]benzofuran derivatives was synthesized by electrophilic aromatic substitutions, such as bromination, formylation and acylation, to investigate the influence of the substituents on the conformations of the calix[3]benzofurans. H-1 NMR spectral analyses of the acyl derivatives at room temperature indicated that these macrocycles exist as a mixture of two isomers that are slowly interconverted on the H-1 NMR timescale. The conformational isomers of the calix[3]benzofurans and their derivatives obtained from DFT methods (based on the crystal structure analysis results) were used to estimate the total energies of the different conformations.

机译：CALIX [3]苯并呋喃通过改性的TOSMIC偶联反应合成，然后用酸处理和与TMSI（三甲基甲硅烷基碘）的分子内环化反应; X射线分析建立了两个样品的结构，既显示锥形构象。 Calix的H-1 NMR光谱分析[3]苯并呋喃（Benzofurans）显示它们可以在溶液中采用急剧不同的构象，并相对于NMR时间尺度进行非常快的构象变化。 CALIX [3]苯并呋喃4a作为两个塑壳，即锥形和鞍形式，以83：17在-50℃下的比例。一系列CALIX [3]苯并呋喃衍生物被亲电芳族取代合成，例如溴化，甲酰化和酰化，研究取代基对CALIX [3]苯并呋喃的构象的影响。在室温下的酰基衍生物的H-1 NMR光谱分析表明，这些宏杂种作为两种异构体的混合物存在，其在H-1 NMR秒表上缓慢地互连。 CALIX [3]苯并呋喃的构象异构体及其从DFT方法获得的衍生物（基于晶体结构分析结果）来估计不同构象的总能量。

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来源
《RSC Advances》 |2016年第56期|共10页
作者
Islam Md Monarul; Akther Thamina; Ikejiri Yusuke; Matsumoto Taisuke; Tanaka Junji; Rahman Shofiur; Georghiou Paris E.; Hughes David L.; Redshaw Carl; Yamato Takehiko;
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作者单位

Saga Univ Fac Sci &

Engn Dept Appl Chem Honjo Machi 1 Saga Saga 8408502 Japan;

Saga Univ Fac Sci &

Engn Dept Appl Chem Honjo Machi 1 Saga Saga 8408502 Japan;

Saga Univ Fac Sci &

Engn Dept Appl Chem Honjo Machi 1 Saga Saga 8408502 Japan;

Kyushu Univ Inst Mat Chem &

Engn 6-1 Kasugakoen Kasuga Fukuoka 8168580 Japan;

Kyushu Univ Inst Mat Chem &

Engn 6-1 Kasugakoen Kasuga Fukuoka 8168580 Japan;

Mem Univ Newfoundland Dept Chem St John NF A1B 3X7 Canada;

Mem Univ Newfoundland Dept Chem St John NF A1B 3X7 Canada;

Univ E Anglia Sch Chem Norwich NR4 7TJ Norfolk England;

Univ Hull Dept Chem Cottingham Rd Kingston Upon Hull HU6 7RX N Humberside England;

Saga Univ Fac Sci &

Engn Dept Appl Chem Honjo Machi 1 Saga Saga 8408502 Japan;

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Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans

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