Theoretical study of the formation of a spiro-Sn-heterocyclic compound by cycloaddition reaction of Me2C=Sn: and ethene

IF 1.3 3区化学 Q3 CHEMISTRY, ORGANIC

Heterocyclic Communications Pub Date : 2018-12-19 DOI:10.1515/hc-2018-0129

Xiaojun Tan, Xiuhui Lu

引用次数: 1

Abstract

Abstract X2C=Sn: compounds (X=H, Me, F, Cl, Br, Ph, Ar) are new species. The cycloaddition reactions of X2C=Sn: are also a new study field of unsaturated stannylene chemistry. The mechanism of cycloaddition reaction between singlet Me2C=Sn: and ethene was investigated for the first time using the MP2/GENECP (C, H in 6-311++G**; Sn in LanL2dz) method. From the potential energy profile, it was predicted that the reaction has one dominant channel in which the 5p unoccupied orbital of Sn: in Me2C=Sn: and the π orbital of ethene form a π→p donor-acceptor bond in an intermediate product. Instability of the intermediate product results in its isomerization to a four-membered ring of stannylene. The four-membered stannylene further combines with ethene to form another intermediate product that further isomerizes to a spiro-Sn-heterocyclic ring compound.

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Me2C=Sn:与乙烯环加成反应生成螺-Sn杂环化合物的理论研究

文摘X2C=Sn：化合物（X=H，Me，F，Cl，Br，Ph，Ar）为新物种。X2C=Sn的环加成反应也是不饱和亚锡化学的一个新的研究领域。用MP2/GENECS（C，H在6-311++G**；Sn在LanL2dz）方法首次研究了单线态Me2C=Sn:与乙烯的环加成反应机理。根据势能分布，预测反应有一个主要通道，其中Sn的5p未占据轨道：在Me2C=Sn中：和乙烯的π轨道形成π→中间产物中的p供体-受体键。中间产物的不稳定性导致其异构化为亚锡的四元环。四元亚锡进一步与乙烯结合形成另一种中间体产物，该中间体产物进一步异构化为螺锡杂环化合物。

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

Heterocyclic Communications 化学-有机化学

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

1.4 months

期刊介绍： Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.