13402-30-7Relevant academic research and scientific papers
Enantioselective organocatalytic Biginelli reaction: Dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality
Saha, Satyajit,Moorthy, Jarugu Narasimha
supporting information; experimental part, p. 396 - 402 (2011/04/17)
From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to pro
Migrations in Oxidations of Mesidine
Goldstein, Stephen L.,McNelis, Edward
, p. 1613 - 1620 (2007/10/02)
The oxidation of mesidine in methanolic media by ferricyanide, dichromate, and persulfate afforded an anil 4 containing a shifted methoxymethyl group in addition to the principal anil 3 formed by oxidative dealkylation.Possible intermediates 6, 7, and 8 were prepared and oxidized to the product anils.Oxidations of related anilines 9, 10, and 13 did not parallel those of mesidine but afforded analogues of 3.There is significant spectral evidence for anils with alkyl shifts but little for anils analogous to 4.
Nitration of Some 2-Iodo-1,3,5-trialkylbenzenes. Competition between Nitrodeprotonation and Nitrodeiodination. Discussion of Steric Effects
Johansson, Ingegaerd
, p. 723 - 730 (2007/10/02)
The nitration of some 2-iodo-1,3,5-trialkylbenzenes in a nitric acid-nitromethane medium has been investigated.The nitronium ion is found to replace three different substituents competitively, hydrogen, iodine or, to a smaller extent, an alkyl group.The expelled iodonium ion forms some iodo electrophile, which attacks the substrate in a secondary reaction and gives rise to a 2,4-diiodo-1,3,5-trialkylbenzene, which is then nitrodeiodinated.The product of this last reaction and that of the primary nitrodeprotonation are identical, which makes a careful kinetic analysis necessary.The true ratio between the nitrodeiodination and the nitrodeprotonation rate constants is determined via a simulation of the course of the total reaction.The rate ratios have been determined for eight iodotrialkylbenzenes with different steric properties and found to vary with the degree of branching in the alkyl substituents.The nitrodeiodination is favoured when the branching is in the α-position of each chain and disfavoured when the branching is in the β-position.The nitrodeiodination-nitrodeprotonation rate ratio is invariant with the medium, and the product-determinig transition states are thus similar for the two reactions.
