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Paper | Regular issue | Vol 65, No. 1, 2005, pp.9-22
Published online, 16th November, 2004
DOI: 10.3987/COM-04-10120
The Thorpe-Ingold Effect in Glutarimide Derivatives. Part II

Michal Pawlowski, Jan K. Maurin, Andrzej Leniewski, Krystyna Wojtasiewicz, and Zbigniew Czarnocki*

*Faculty of Chemistry, Warsaw University, Pasteura St.1, 02-093 Warsaw, Poland

Abstract

Differently substituted glutarimides, 3-methylglutarimide (12), 3,3-dimethylglutarimide (14) and 3,3,4,4-tetramethylglutarimide (18) were prepared and their reactivity towards aryllithiums was investigated. The influence of Thorpe-Ingold effect on the distribution of products in tautomeric equilibrium was observed together with a total regioselectivity of the process. For imide (12) only keto amide (13) was isolated. Imide (14) resulted in formation both hydroxy lactam (16) and keto amide (15), and imide (18) gave only hydroxy lactam (24).