828-60-4Relevant academic research and scientific papers
Nitrone Formation by Reaction of an Enolate with a Nitro Group
Shimizu, Hiroaki,Yoshinaga, Kohei,Yokoshima, Satoshi
, p. 2704 - 2709 (2021/04/12)
Ketones with a 2-nitrophenyl group at the α-position were treated with sodium hydroxide in methanol at 60 °C. Under these conditions, enolates derived from the ketones intramolecularly reacted with the nitro group to form a variety of nitrones. Additional experimental results, including the unexpected isolation of N-hydroxyindolinone as a byproduct, led to a proposed reaction mechanism, occurring via an α-hydroxyketone. The resultant nitrones underwent inter- and intramolecular 1,3-dipolar cycloaddition with olefins to afford polycyclic isoxazolidines.
Rearrangement of Ketones. Part 4. Aluminium Chloride Catalysed Rearrangement of Some 2,2-Dialkyl-1-phenyl-1-propan-1-ones
Fernandez-Monreal, Maria C.,Ruiz, Maria P.
, p. 440 - 472 (2007/10/02)
Four α,α,α-trisubstituted acetophenones ((1):R1=R2=R3=CH3; (2):R1=R2=CH3, R3=CH2CH3; (3):R1=R2=CH3, R3=CH2Ph; (4):R1=CH3, R2=CH2CH3, R3=CH2Ph) were prepared.Ketones (1)-(4) were treated with aluminium chloride to induce rearrangement to alkyl ketones.The phenyl ketones behaved as follows: (1) gave 3-methyl-3-phenylbutan-2-one (7), (2) gave 3-methyl-3-phenylpentan-2-one (8) and 2-methyl-2-phenylpentan-3-one (9), (3) gave 3-methyl-3,4-diphenylbutan-2-one (10) and 3-methyl-1,3-diphenylbutan-2-one (11), and (4) gave 3-methyl-1,3-diphenylpentan-2-one (12), 2-methyl-1,2-diphenylpentan-3-one (13) and 3-benzyl-3-phenylpentan-2-one (14).A tentative mechanism for the rearrangement is proposed.
