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Stereoselective phenyl migration from silicon to carbon

✍ Scribed by Armido Studer; Martin Bossart; Hanno Steen

Book ID
104260224
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
253 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the present letter, the first stereoselective radical 1,5 phenyl transfer from silicon to carbon is reported. Diphenyl(trimethylsilyl)silyl ethers, the corresponding germylated and stannylated derivatives, and also some silyl ethers derived from commercially available silicon protecting groups were tested in this ipso substitution reaction. Diastereoselectivities of up to 11:1 were obtained.

πŸ“œ SIMILAR VOLUMES

Mass spectral rearrangements of siliconi
Mass spectral rearrangements of siliconium ions-phenyl migration from carbon to silicon
✍ William P. Weber; Raymond A. Felix; Alvin K. Willard πŸ“‚ Article πŸ“… 1970 πŸ› Elsevier Science 🌐 French βš– 179 KB

We have observed in the mass spectrum of 1-phenyl-Z-trimethylsilylethanel a novel intramolecular rearrangement of the phenyl group from carbon to a positively charged silicon center. The base peak at m/e = 73 is due to the trimethylsiliconium ion, while the peak at m/e = 163 results from loss of a