Addition of a stable dialkylsilylene to carbon–carbon unsaturated bonds

✍ Scribed by Shintaro Ishida; Takeaki Iwamoto; Mitsuo Kira

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 163 KB
• Volume: 22
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20705

✦ Synopsis

Abstract

The reactions of an isolable dialkylsilylene, 2,2,5,5‐tetrakis(trimethylsilyl)silacyclopentan‐1,1‐diyl (1) with ethylene, (Z)‐2‐butene, acetylene, bis(trimethylsilyl)acetylene, and 2,3‐dimethylbutadiene at room temperature gave the corresponding silacycles as isolable compounds. Because of the large steric hindrance, the reaction of 1 with (E)‐2‐butene gave a complex mixture, indicating no formation of the corresponding silirane. The reaction of 1 with 2,3‐dimethylbutadiene afforded the corresponding [1 + 4] cycloadduct without contamination of the [1 + 2] cycloadduct. Stable C‐unsubstituted silirane and silirene produced by the reactions of 1 with ethylene and acetylene were analyzed by X‐ray crystallography. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:432–437, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20705