A tris(dialkylamino)sulfonium phenoxide

✍ Scribed by R. Noyori; I. Nishida; J. Sakata

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 267 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82046-3

✦ Synopsis

The title phenoxide has been prepared from phenyl trimethylsilyl ether and tris-(diethylamino)sulfonium difluorotrimethylsiliconate. The conductivity measurement and NMR analysis indicate that this phenoxide dissociates into the ions in THF solution. Phenoxide and enolates are an important class of anionic species. The structures and reactivities are known to be profoundly affected by'the nature of the counter cations and n the solvents . ' As a part of our study on superanions wl-uch possess negligible bonding interaction with their counter cations, 1,3,4 we have synthesized a tris(dialkylamino)sulfonmm phenoxide as is disclosed herein. Phenyl trimethylsilyl ether (I) in THF exhibits an 1H NMR signal at d 0.26 due to the Si-CH3 protons, and tris(diethylamino)sulfonium (TAS) difluorotrimethylsiliconate (IIj5 gives the corresponding signal as singlet at 6 -0.18. However, when these two substances were mixed in 1:l mol ratio in THF, the 'H NMR spectrum showed only a single Si-CH signal at 6 0.19, suggesting the occurrence of dynamic equilibria depicted in eq 1 and 2.