Understanding the mechanism of the 1,3-dipolar cycloaddition reaction between a thioformaldehyde S-oxide and cyclobutadiene: Competition between the stepwise and concerted routes

IF 2.1 4区 化学 Q3 CHEMISTRY, PHYSICAL
B. Mohtat, Seyyed Amir Siadati, M. Khalilzadeh
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引用次数: 3

Abstract

Changing the mechanism of the widely used 1,3-dipolar cycloaddition reaction from its usual asynchronous one-step pattern to the rarely observed stepwise form leads to the emergence of intermediates, side products, and other impurities. Thus, it is crucial to determine the nature of the mechanism of the 1,3-dipolar cycloaddition reaction between a special 1,3-dipole and a specified dipolarophile (by theoretical methods) before using them for synthesizing a desired product. In this study, therefore, we have investigated the possibility of some probable intermediates emergence in the 1,3-dipolar cycloaddition reaction between cyclobutadiene and thioformaldehyde S-oxide. The results showed that emergence of Int (B) (−52.1 kcal mol−1) via transition state (B-1) is favorable both thermodynamically and kinetically (in comparison with all other stepwise routes). That is, developing probable impurities should not be neglected at least in the cases of the reactions between some thioformaldehyde S-oxide and some dipolarophiles.
硫代甲醛s -氧化物与环丁二烯1,3-偶极环加成反应机理的研究:步进和协同反应途径的竞争
将广泛使用的1,3偶极环加成反应的机理从其通常的异步一步模式改变为很少观察到的逐步形式,导致中间产物,副产物和其他杂质的出现。因此,在使用特定的1,3偶极子和特定的亲偶极试剂合成所需的产物之前,通过理论方法确定它们之间的1,3偶极环加成反应的性质是至关重要的。因此,在本研究中,我们研究了在环丁二烯和硫代甲醛s -氧化物之间的1,3-偶极环加成反应中可能出现一些中间体的可能性。结果表明,在热力学和动力学上,通过过渡态(B-1)产生Int (B) (- 52.1 kcal mol -1)都是有利的(与所有其他逐步途径相比)。也就是说,至少在某些硫代甲醛s -氧化物与某些亲偶极试剂之间的反应中,不应忽视可能产生的杂质。
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
CiteScore
2.10
自引率
0.00%
发文量
5
审稿时长
2.3 months
期刊介绍: The journal covers the fields of kinetics and mechanisms of chemical processes in the gas phase and solution of both simple and complex systems.
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