A base-stabilized 2-silaallene

• Main Authors: Yang, Yi-Fan, Foo, Cechao, Xi, Hong Wei, Li, Yongxin, Lim, Kok Hwa, So, Cheuk-Wai
• Other Authors: School of Chemical and Biomedical Engineering
• Format: Article
• Language: English
• Published: 2013
• Online Access: https://hdl.handle.net/10356/105686; http://hdl.handle.net/10220/16609; http://dx.doi.org/10.1021/om301175p
• Institution: Nanyang Technological University

The reaction of [CH2(PPh2S)2] (1) with 2 equiv of MeLi in Et2O followed by addition of 0.5 equiv of SiCl4 afforded the base-stabilized 2-silaallene [(PPh2S)2CSiC(PPh2S)2] (2). It has been characterized by X-ray crystallography, NMR spectroscopy, and theoretical studies. The results show that compound 2 comprises a C¯–Si2+–C¯ ylidic skeleton with a negative charge at the Cmethanediide atoms and two positive charges at the Si atom. The reaction of 2 with excess PriN═C═NPri in refluxing toluene gave the thiophosphinoyl-stabilized silene [(PPh2S)2C–—Si+(NPri)2C═C(PPh2S)2] (3).