50336-92-0Relevant academic research and scientific papers
Tertiobutylation de quelques cetones alicycliques et aliphatiques via leurs ethers d'enol trimethylsilyliques. Influence de l'environnement du carbonyle sur le deroulement de la reaction
Lion, Claude,Dubois, Jacques-Emile
, p. 375 - 379 (2007/10/02)
α-Tertiobutylation of aliphatic ketones via their trimethylsilyl enol ethers has been extended to the alicyclic series.A comparative study of the alkylation of ketones in both series with identical steric hindrance has been undertaken.The efficiency and limits of the reaction have been determinated by progressive substitution α and α' to the carbonyl.
Lewis Acid Mediated α-Alkylation of Carbonyl Compounds, VII. Regio and Position Specific α-tert-Alkylation of Ketones
Reetz, Manfred T.,Maier, Wilhelm F.,Chatziiosifidis, Ioannis,Giannis, Athanassios,Heimbach, Horst,Loewe, Ursula
, p. 3741 - 3757 (2007/10/02)
Structurally different ketones can be alkylated at the α-position via their silyl enol ethers with tert-alkyl halides in the presence of Lewis acids such as titanium tetrachloride (->27 - 35).Concerning the alkylation agent, the position specific introduction of branched and cyclic tert-alkyl groups is possible (->41 - 49).Bridgehead halides of the type 1-adamantyl bromide react analogously (->52 - 61).Silyl enol ethers derived from unsymmetrical ketones react regiospecifically (->63, 64, 66, 67).If the reaction partners contain additional functional groups such as aryl residues (->68, 69) or ester groups (->71) or primary alkyl halides moieties (->73), selectivity in the desired manner is observed. α,α'-Bis-tert-alkylated ketones (74 - 76) are also easily accessible, but not the α,α-isomers.
