64853-55-0Relevant academic research and scientific papers
Hydrogen Borrowing Catalysis with Secondary Alcohols: A New Route for the Generation of β-Branched Carbonyl Compounds
Akhtar, Wasim M.,Cheong, Choon Boon,Frost, James R.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.
supporting information, p. 2577 - 2580 (2017/03/01)
A hydrogen borrowing reaction employing secondary alcohols and Ph? (Me5C6) ketones to give β-branched carbonyl products is described (21 examples). This new C-C bond forming process requires low loadings of [Cp?IrCl2]2, relatively low temperatures, and up to 2.0 equiv of the secondary alcohol. Substrate-induced diastereoselectivity was observed, and this represents the first example of a diastereoselective enolate hydrogen borrowing alkylation. By utilizing the Ph? group, the β-branched products could be straightforwardly cleaved to the corresponding esters or amides using a retro-Friedel-Crafts reaction. Finally, this protocol was applied to the synthesis of fragrance compound (±)-3-methyl-5-phenylpentanol.
Regioselective Side-Chain Nitration of Polymethylbenzenes Directed by an Acyl Function and Its Application to the Synthesis of Polysubstituted Phthalic Acid Derivatives
Keumi, Takashi,Morita, Toshio,Teramoto, Koichi,Takahashi, Hisakazu,Yamamoto, Hiroshi,et al.
, p. 3439 - 3446 (2007/10/02)
Nitration of three types of tetramethylacetophenones and pentamethylacetophenone with fuming nitric acid in acetic anhydride was carried out.The product distributions were compared with those estimated from substituent effects.A variety of acylpentamethylbenzenes including pentamethylbenzoic acid were reacted with the nitrating system to give regioselectively 2-(nitromethyl)-3,4,5,6-tetramethylacylbenzenes.The selective nitrations of some benzoic acid derivatives followed by an alkaline treatment have been found to provide the N-hydroxyphthalimide derivatives, which a re readily converted to the phthalic anhydrides and the phthalazines.
