A Tin Analogue of the Cycloheptatrienyl Anion: Synthesis, Structure, and Further Reduction to Form a Dianionic Species,Organometallics

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A Tin Analogue of the Cycloheptatrienyl Anion: Synthesis, Structure, and Further Reduction to Form a Dianionic Species
Organometallics ( IF 2.5 ) Pub Date : 2020-02-24 , DOI: 10.1021/acs.organomet.0c00042
Shotaro Ito ₁ , Takuya Kuwabara ₁ , Youichi Ishii ₁

Affiliation

The synthesis and electronic structure of a tin analogue of the cycloheptatrienyl anion are described. The reaction of 5,5-diphenyldibenzo[b,f]stannepin with lithium at low temperatures reductively cleaved a Sn–Ph bond to give a lithium salt of the stannepinyl anion, the structure of which was established by X-ray diffraction analysis. Elongating the reaction time resulted in further reduction of the other Sn–Ph bond to generate a dilithium species, the formation of which was confirmed by a trapping reaction using MeI. Unlike general cycloheptatrienyl anions, the monoanionic species was proved to be nonaromatic on the basis of the NMR and X-ray diffraction studies. When the reduction was carried out at room temperature, decomposition of the seven-membered ring followed by Z/E isomerization promoted by lithium proceeded to generate (E)-2,2′-dilithiostilbene, which forms a dimer in the crystalline state.

中文翻译：

环庚三烯基锡的锡类似物：合成，结构和进一步还原，以形成阳离子物种。

描述了环庚三烯基阴离子的锡类似物的合成和电子结构。5，5-二苯基二苯并[ b，f ] stannepin与锂在低温下的反应还原性裂解Sn-Ph键，得到锡萘吡啶基阴离子的锂盐，其结构通过X射线衍射分析确定。延长反应时间会导致其他Sn-Ph键的进一步还原，从而生成双锂物种，通过使用MeI进行的捕集反应可以证实其形成。与一般的环庚三烯基阴离子不同，在NMR和X射线衍射研究的基础上，单阴离子物质被证明是非芳香族的。当在室温下进行还原时，七元环分解，然后锂促进的Z / E异构化过程继续产生（E）-2,2'-dilithiostilbene，它在结晶状态下形成二聚体。

更新日期：2020-02-24

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