ChemInform Abstract: Novel Oxidative Generation of Ammonium Ylides and the Subsequent Silicon Polonovski Reaction.

Abstract

2008Carboxylic amides P 0320Novel Oxidative Generation of Ammonium Ylides and the Subsequent Silicon Polonovski Reaction. -Treatment of N-(α-silylmethyl)-N-allylic amines such as (I) with an oxidant, followed by acetic anhydride (II) leads to a tandem Brook rearrangement/silicon Polonovski reaction via the generation of ammonium ylides to give the corresponding amides (III). A similar reaction with the α-cyano derivatives (IV) affords formamides (V). -(HONDA*, K.; SHIBUYA, H.; HOSHINO, Y.; INOUE, S.; Chem. Lett. 37 (2008) 4, 442-443; Grad. Sch. Eng., Yokohama Natl. Univ., Hodogaya, Yokohama 240, Japan; Eng.) -M. Paetzel 33-064