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

Heterocyclic communications

article

Xiaojun Tan¹  Xiuhui Lu² 

[1] School of Biological Science and Technology, University of Jinan;School of Chemistry and Chemical Engineering, University of Jinan

关键词: four-membered stannylene;    Me2C=Sn;    potential energy profile;    spiro-Sn-heterocyclic compound;   

DOI  :  10.1515/hc-2018-0129

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

X 2 C=Sn: compounds (X=H, Me, F, Cl, Br, Ph, Ar) are new species. The cycloaddition reactions of X 2 C=Sn: are also a new study field of unsaturated stannylene chemistry. The mechanism of cycloaddition reaction between singlet Me 2 C=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 Me 2 C=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.

【 授权许可】

CC BY|CC BY-NC-ND