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Merck

[New development of ammonium ylide chemistry].

Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan (1994-11-01)
Y Sato, N Shirai
ABSTRACT

Benzylammonium N-alkylides were generated by reaction of N-[1-(trimethylsilyl)alkyl]benzylammonium salts with cesium fluoride in DMF or HMPA, and their rearrangement products were investigated. [2,3]Sigmatropic rearrangement of the ylides initially occurred to give isotoluene derivatives and then they were transformed into Sommelet-Hauser rearrangement products and/or Stevens products. The isotoluenes having bicyclic structures were stable at room temperature and aromatized with the aid of a base. The relationship between the configuration of cyclic ammonium ylides and the rearrangement paths is described.

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Sigma-Aldrich
Cesium fluoride, 99%
Sigma-Aldrich
Cesium fluoride, 99.9% trace metals basis
Sigma-Aldrich
Cesium fluoride, purum p.a., ≥98.0%
Sigma-Aldrich
Cesium fluoride, 99.99% trace metals basis
Sigma-Aldrich
Cesium fluoride, BioUltra, ≥99.0% (F)