Stable Strained Donor-Free Silanone and Its Derived NHC-Stabilized Disilacyclobutadiene and Cyclic Alkenyl SilyleneClick to copy article linkArticle link copied!
- Yazhou DingYazhou DingState Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of ChinaMore by Yazhou Ding
- Wen JinWen JinState Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of ChinaMore by Wen Jin
- Chen-Huan LiuChen-Huan LiuState Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of ChinaMore by Chen-Huan Liu
- Jianying ZhangJianying ZhangState Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of ChinaMore by Jianying Zhang
- Chunming Cui*Chunming Cui*Email: [email protected]State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of ChinaMore by Chunming Cui
Abstract

The strained silanone 2 was obtained by the reaction of disilacyclobutene 1 with N2O. Silanone 2 exhibited unprecedented thermal stability in both the solid state and solution. DFT calculations on 2 revealed that the highly polarized Si═O double bond is effectively stabilized by its electron delocalization with the unsaturated Si2C2 ring. Treatment of 2 with 1,3,4,5-tetramethylimidazolin-2-ylidene yielded the first Lewis base-stabilized disilacyclobutadiene 3 via a 1,3-boryl migration. Reaction of 2 with HCCH and Me3SiN3 resulted in the addition of C–H and Si–N bonds to the Si═O double bond. Interestingly, irradiation of 2 at rt yielded oxosilanes 7A and 7B in C6D6 and n-hexane, respectively, via the 1,2-boryl migration and ring expansion, whereas photolysis at −60 °C led to the formation of cyclic alkenyl silylene 8.
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, 34979-34989. https://doi.org/10.1021/jacs.4c15062
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