ChemInform Abstract: Aryl Trialkylsilyl Ketenes: Acid‐Catalyzed Synthesis from 1‐Aryl‐2‐diazo‐2‐trialkylsilylethanones and Their Conversion into 3‐Silyl‐1‐silyloxyallenes.

Abstract

Ketenes and derivatives Q 0380Aryl Trialkylsilyl Ketenes: Acid-Catalyzed Synthesis from 1-Aryl-2-diazo-2-trialkylsilylethanones and Their Conversion into 3-Silyl-1-silyloxyallenes. -A convenient method to prepare silyl ketenes of type (IV) combines silylation of aryl diazomethyl ketones and an acid-induced Wolff rearrangement of the intermediate silyl diazo ketones in one pot. The rearrangement can be catalyzed either by a proton acid such as TfOH or distinctly more slowly by the trialkylammonium salt which is formed in the silylation step. Reaction of the silyl ketones with silyl diazo ketones such as (VI) gives the 3-silyl-1-silyloxyallenes (VII). -(BUCHER, S. M.; BRUECKMANN, R.; MAAS*, G.; Eur.