ChemInform Abstract: Reactions of Alkyl Azides and Ketones as Mediated by Lewis Acids: Schmidt and Mannich Reactions Using Azide Precursors.
Abstract
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ChemInform Abstract
Reactions of ketones with alkyl azides in the presence of either TiCl4 or TfOH are investigated in continuation of previously published studies. In general, simple cyclic ketones with 3, 4 and 6 ring members undergo Schmidt reactions with benzyl azide in the presence of TiCl4 while cyclic ketones with 5 or more than 6 members as well as acyclic ketones undergo azido-Mannich reactions after rearrangement of the benzyl azide. These Mannich-type reactions are most efficiently mediated by TfOH. Some bridged systems prefer the Schmidt pathway. The results are discussed based on steric and conformational considerations.
