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Synthesis and Characterization of Bromonium Ylides and Their Unusual Ligand Transfer Reactions with N-Heterocycles

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posted on 02.08.2006, 00:00 by Masahito Ochiai, Norihiro Tada, Kentaro Murai, Satoru Goto, Motoo Shiro
Stable aliphatic bromonium ylides (RfSO2)2C-−Br+C6H4-p-CF3 (Rf = CF3, CF3(CF2)3) have been synthesized and structurally characterized for the first time. X-ray crystallographic analyses indicated a ylide structure with an sp2 hybridization of the ylide carbanions and with little double-bond character for the ylidic bond. The bromonium ylides selectively undergo transfer of the aryl group to nitrogen heterocycles, such as pyridines, yielding N-arylpyridinium salts. This is in a marked contrast to the reaction of the iodonium ylides, which produces pyridinium ylides through transylidations.