[New development of ammonium ylide chemistry].
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.
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
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Y
Sato
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N
Shirai
D001548:Benzalkonium Compounds / Q000737:chemistry; D002586:Cesium; D005459:Fluorides; D006492:Hempa; D008968:Molecular Conformation; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D001548:Benzalkonium Compounds; D000644:Quaternary Ammonium Compounds; D014297:Trimethylsilyl Compounds; D002586:Cesium; D006492:Hempa; D005459:Fluorides; C027754:cesium fluoride