A comparative study of thallium(III) and iodine(III)-mediated ring contraction reactions for the synthesis of indane,New Journal of Chemistry

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A comparative study of thallium(III) and iodine(III)-mediated ring contraction reactions for the synthesis of indane
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2020-12-18 , DOI: 10.1039/d0nj04700g
Ajmir Khan _{1,

2,

3,

4,

5} , Luiz F. Silva _{1,

2,

3,

4,

5} , Muhammad Rabnawaz _{6,

7,

8,

9}

Affiliation

Reported herein is a comparative study of the synthesis of indane via ring contraction reaction, mediated by iodine(III) and thallium(III). A series of protected 1,2-dihydronaphthalenes were synthesized and subjected to hydroxy(tosyloxy)iodobenzene (HTIB) and thallium(III) nitrate trihydrate (TTN) in trimethyl orthoformate (TMOF) to compare the percent yields provided by both oxidizing agents. The yields of the ring contracted products (indanes) were in the range of 61–88% for reactions performed with TTN·3H₂O in TMOF. However, the yields were found to be significantly lower (e.g., 18–34%) when using HTIB in TMOF with some addition products. This study provides an important development related to the efficacy of the two oxidizing agents for ring contraction reaction.

中文翻译：

al和碘介导的环缩合反应合成茚满的比较研究

本文报道了由碘（III）和th（III）介导的通过环收缩反应合成茚满的比较研究。合成了一系列受保护的1,2-二氢萘，并使其在原甲酸三甲酯（TMOF）中经受羟基（甲苯磺酰氧基）碘苯（HTIB）和硝酸al （III）三水合物（TTN）的比较，以比较两种氧化剂提供的收率百分比。用TOF·3H ₂ O在TMOF中进行的反应，环缩合产物（茚满）的收率在61–88％的范围内。但是，发现产量要低得多（例如（18-34％）时，在TMOF中将HTIB与某些其他产品一起使用。这项研究提供了与两种氧化剂对环收缩反应的功效有关的重要进展。

更新日期：2021-01-18

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