42981-75-9Relevant academic research and scientific papers
Chromic Acid Oxidation of Indans and Tetralins to 1-Inadanones and 1-Tetralones Using Jones and Other Cr(VI) Reagents
Rangarajan, Radhika,Eisenbraun, E.J.
, p. 2435 - 2438 (2007/10/02)
The Jones chromic acid oxidation, ordinarily used for converting secondary alcohols to ketones, has been successfully extended to the oxidation of indans and tetralins to 1-indanones and 1-tetralones, respectively.A sixfold excess of the reagent was commonly used to ensure complete oxidation of starting material.Addition of anhydrous magnesium sulfate or oven-dried silica gel provided a yield increase of 15-20percent. 2,2'-Bipyridinium chlorochromate was also used and found to be effective in all cases, but this reagent requires a longer reaction time and a 16-fold excess.A comparison between these two reagents and CrO3 in acetic acid was made.The Jones reagent being least selective, gives the highest yield of sterically hindered monoketone from 1,2,3,4,5,6,7,8-octahydrophenanthrene.
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.
