16423-52-2Relevant articles and documents
Hydrophobic effect and substrate specificity in reaction of thioester and amine in water
Torihata, Atsushi,Kuroda, Chiaki
, p. 1534 - 1538 (2010)
The extent of hydrophobic effect in amidation reaction of alkyl thioester with alkylamine in water was studied. The yield of the products was primarily dependent on the alkyl group of amine. For example, the reaction of S-dodecyl dodecanethioate with dodecylamine proceeded in good yield, while the reaction did not occur with cyclohexylamine, piperidine, and dipropylamine. The effect of chain length of n-alkylamine was studied to suggest the presence of hydrophobic effect. The yield of amide also depended on the alkyl group of the thioester secondarily, but the effect was smaller than amine.
Alkyl perchlorates in the Ritter-type reaction. Synthesis of N-alkylamides
Yashin,Markov,Sedenkova,Vasilenko,Grishin, Yu. K.,Kuznetsova,Averina
, p. 980 - 985 (2020)
The Ritter-type reaction of alkyl perchlorates with nitriles of various structures was systematically studied. The reaction has a wide scope and proceeds under extremely mild conditions without any catalysts or special activation of reagents. A structural diversity of the obtained by the Ritter-type reaction N-alkyl amides bearing small ring, double bonds, additional functional groups, aromatic and adamantane fragments, was demonstrated.
Method for preparing primary and secondary amide compounds
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Paragraph 0178-0187, (2021/02/06)
The invention belongs to the field of organic chemical synthesis, and particularly relates to a method for preparing primary and secondary amide compounds. The method for preparing primary and secondary amide compounds comprises the following steps of carrying out catalytic reduction on an N-substituted amide compound at 30-130 DEG C by using a protic solvent as a reduction reagent and a dichloro(p-methyl isopropylbenzene) ruthenium (II) dimer complex as a catalyst to obtain a reaction solution after the reduction reaction is finished, and carrying out post-treatment on the reaction solution to obtain the corresponding primary amide compound or secondary amide compound. According to the method for preparing the primary and secondary amide compounds, the transfer hydrogenation reaction of nitrogen-oxygen and nitrogen-carbon bonds is realized, the reaction conditions are mild and simple, the substrate application range is wide, the operation is convenient, and the corresponding primary amide compound or secondary amide compound is obtained with high efficiency and high selectivity.
Overriding Intrinsic Reactivity in Aliphatic C?H Oxidation: Preferential C3/C4 Oxidation of Aliphatic Ammonium Substrates
Heilmann, Michael,Knezevic, Melina,Piccini, Giovanni Maria,Tiefenbacher, Konrad
, p. 12387 - 12391 (2020/07/04)
The site-selective C?H oxidation of unactivated positions in aliphatic ammonium chains poses a tremendous synthetic challenge, for which a solution has not yet been found. Here, we report the preferential oxidation of the strongly deactivated C3/C4 positions of aliphatic ammonium substrates by employing a novel supramolecular catalyst. This chimeric catalyst was synthesized by linking the well-explored catalytic moiety Fe(pdp) to an alkyl ammonium binding molecular tweezer. The results highlight the vast potential of overriding the intrinsic reactivity in chemical reactions by guiding catalysis using supramolecular host structures that enable a precise orientation of the substrates.
