A REVIEW. Have questions or comments? Hydroxylamine- Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO–NHOH) to anilines. In lieu of an abstract, this is the article's first page. The direct reaction of a carboxylic acid with an amine would be expected to be difficult because the basic amine would deprotonate the carboxylic acid to form a highly unreactive carboxylate. Journal of Synthetic Organic Chemistry, Japan. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. Fremeijer, Douwe A. Wiersma. -PROTECTED HYDROXYLAMINES AS REAGENTS IN ORGANIC SYNTHESIS. A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines. Get article recommendations from ACS based on references in your Mendeley library. These metrics are regularly updated to reflect usage leading up to the last few days. The direct conversion of a carboxylic acid to an amide is difficult because amines are basic and tend to convert carboxylic acids to their highly unreactive carboxylates. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. -sulfonic Acid. https://doi.org/10.1134/S1070428020090110, https://doi.org/10.5059/yukigoseikyokaishi.75.746, https://doi.org/10.1016/j.tetlet.2016.10.037, https://doi.org/10.1002/047084289X.rh058.pub2, https://doi.org/10.1002/9780471264194.fos05731, https://doi.org/10.1002/9780470125946.ch7, https://doi.org/10.1007/978-3-322-96805-0_12, https://doi.org/10.1016/S0040-4039(00)01058-3, https://doi.org/10.1016/S0968-0896(99)00090-5, https://doi.org/10.1080/00304949609356535, https://doi.org/10.1007/978-3-322-94726-0_66, https://doi.org/10.1016/S0040-4039(00)61187-5, https://doi.org/10.1016/B978-0-08-092553-0.50044-3, https://doi.org/10.1016/B978-0-08-052349-1.00172-4, https://doi.org/10.1016/B978-0-08-092558-5.50018-6, https://doi.org/10.1080/00397918308082718, https://doi.org/10.1016/B978-0-08-092556-1.50017-8, https://doi.org/10.1080/00304948209354920, https://doi.org/10.1016/0301-0104(76)87039-5, https://doi.org/10.1016/B978-0-12-618553-9.50018-3, https://doi.org/10.1016/S0040-4039(00)99740-5. In this reaction the carboxylic acid adds to the DCC molecule to form a good leaving group which can then be displaced by an amine during nucleophilic substitution. The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Kaushik Chakrabarti, Kuheli Dutta, Sabuj Kundu. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. Poddubny. New calcium antagonists: synthesis, X-ray analysis, and smooth muscle relaxing effect of 3-[ O -(Benzyl-substituted)-oximino-ethers]-hexahydroazepin-2,3-diones. ITS USE IN ORGANIC SYNTHESIS. 31 publications. Organic Preparations and Procedures International. Spontaneous Lossen Rearrangement of (Phosphonoformyl)hydroxamates. Oliver Kreye, Hatice Mutlu, Michael A. R. Meier. bis Journal of Synthetic Organic Chemistry, Japan. Sustainable routes to polyurethane precursors. The carbonyl is now activated toward nucleophilic attack. Hayat El From, Marie-Hélène Péra, Gérard Leclerc, Duc Tranqui, Emmanuelle Corompt, Germain Bessard, Philippe Devillier. Tetrahedron Letters 2016 , 57 (48) , 5304-5307. A. V. Velikorodov, E. N. Kutlalieva, N. N. Stepkina, E. A. Shustova, O. Yu. Optical nuclear polarization in the excited state through cross-relaxation ant its use in the study of the carbon-13 hyperfine coupling in the lowest triplet state of 1-13C-p-benzoquinone. Watch the recordings here on Youtube! You’ve supercharged your research process with ACS and Mendeley! Note: An acid catalyst is required. -methylated amines from acyl azides using methanol. Photoreduction of .pi.,.pi. Naoya Ohtsuka, Moriaki Okuno, Yujiro Hoshino, Kiyoshi Honda. Please reconnect. 1) Nucleophilic attack on Thionyl Chloride. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. A.Sekar Reddy, M.Suresh Kumar, G.Ravindra Reddy. One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives. the Altmetric Attention Score and how the score is calculated.
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