aDepartment of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, Ukraine bSTC 'Institute for Single Crystals', National Academy of Sciences of Ukraine, Kharkov, Ukraine cA.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine dKirovograd State Pedagogical University, Kirovograd, Ukraine eN.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation
Аннотация:
The XRD studies of N-chloro-N-alkoxyureas 1, 2 have revealed the high pyramidality of the amide nitrogen in the O–N–Cl group caused by nO–O*N–Cl anomeric effect, the other sequence of this effect is anionic lability of the chlorine atom; nucleophilic substitution at the nitrogen depends on the N′-substitutent nature: chlorine atoms in ureas 1 and 5 are replaced by outer nucleophile whereas, under the same conditions, ureas 2–4 undergo cyclization into 1-alkoxybenzimidazolin-2-ones 10–12.
Тип публикации:
Статья
Язык публикации: английский
Образец цитирования:
V. G. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, S. V. Kravchenko, A. V. Tsygankov, A. V. Mazepa, E. A. Klots, R. G. Kostyanovsky, “N-Chloro-N-alkoxyureas: synthesis, structure and properties”, Mendeleev Commun., 16:6 (2006), 323–325
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc3643
https://www.mathnet.ru/rus/mendc/v16/i6/p323
Эта публикация цитируется в следующих 23 статьяx:
Pradeep R. Varadwaj, Arpita Varadwaj, Helder M. Marques, Koichi Yamashita, “Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit”, Crystal Growth & Design, 24:13 (2024), 5494
Vasiliy G. Shtamburg, Evgeniy A. Klots, Victor V. Shtamburg, Andrey A. Anishchenko, Svitlana V. Shishkina, Alexander V. Mazepa, “Nucleophilic substitution at nitrogen atom. N-Alkoxy-N-(dimethoxyphosphoryl)ureas, synthesis and structure”, Journal of Molecular Structure, 1277 (2023), 134865
Vasiliy G. Shtamburg, Victor V. Shtamburg, Andrey A. Anishchenko, Alexander V. Mazepa, Eduard B. Rusanov, “3-Alkoxy-1,5-bis(aryl)imidazolidine-2,4-diones, synthesis and structure”, Journal of Molecular Structure, 1264 (2022), 133259
Stephen A. Glover, Adam A. Rosser, Amide Bond Activation, 2022, 29
Stephen A. Glover, Rhiannon R. Schumacher, “Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation: The role of fluorene and fluorenone substituents as DNA intercalators”, Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 863-864 (2021), 503299
Stephen A. Glover, Adam A. Rosser, “Heteroatom Substitution at Amide Nitrogen—Resonance Reduction and HERON Reactions of Anomeric Amides”, Molecules, 23:11 (2018), 2834
Stephen A. Glover, Adam A. Rosser, “The role of substituents in the HERON reaction of anomeric amides”, Can. J. Chem., 94:12 (2016), 1169
Stereoelectronic Effects, 2016, 97
Stephen A. Glover, Adam A. Rosser, “HERON reactions of anomeric amides: understanding the driving force”, J of Physical Organic Chem, 28:3 (2015), 215
V. G. Shtamburg, R. G. Kostyanovsky, A. V. Tsygankov, V. V. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, A. V. Mazepa, S. V. Kravchenko, “Geminal systems”, Russ Chem Bull, 64:1 (2015), 62
Stephen A. Glover, Adam A. Rosser, Avat (Arman) Taherpour, Ben W. Greatrex, “Formation and HERON Reactivity of Cyclic N,N-Dialkoxyamides”, Aust. J. Chem., 67:3 (2014), 507
Korry L. Barnes, Anna K. Koster, Christopher S. Jeffrey, “Trapping the elusive aza-oxyallylic cation: new opportunities in heterocycloaddition chemistry”, Tetrahedron Letters, 55:34 (2014), 4690
Stephen A. Glover, Adam A. Rosser, Robert M. Spence, “Studies of the Structure, Amidicity, and Reactivity of N-Chlorohydroxamic Esters and N-Chloro-β,β-dialkylhydrazides: Anomeric Amides with Low Resonance Energies”, Aust. J. Chem., 67:9 (2014), 1344
V. G. Shtamburg, O. V. Shishkin, V. V. Shtamburg, R. I. Zubatyuk, A. V. Mazepa, R. G. Kostyanovsky, “N-Alkoxy-N-chloroureas in the synthesis of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide and 1-alkoxy-1,3-dihydrobenzimidazol-2-ones”, Chem Heterocycl Comp, 49:8 (2013), 1195
S. Kubik, Knowledge Updates 2013/3, 2013
Christopher S. Jeffrey, Devendar Anumandla, Christopher R. Carson, “1,4-Diamination of Cyclic Dienes via a (4 + 3) Cycloaddition of Diaza-allyl Cationic Intermediates”, Org. Lett., 14:22 (2012), 5764
V. G. Shtamburg, A. V. Tsygankov, O. V. Shishkin, R. I. Zubatyuk, B. V. Uspensky, V. V. Shtamburg, A. V. Mazepa, R. G. Kostyanovsky, “The properties and structure of N-chloro-N-methoxy-4-nitrobenzamide”, Mendeleev Commun., 22:3 (2012), 164–166
V. G. Shtamburg, A. V. Tsygankov, O. V. Shishkin, R. I. Zubatyuk, V. V. Shtamburg, M. V. Gerasimenko, A. V. Mazepa, R. G. Kostyanovsky, “1-Alkoxyamino-4-dimethylaminopyridinium derivatives as new representatives of O–N–N+ geminal systems and their structure†”, Mendeleev Commun., 22:2 (2012), 92–94
V. G. Shtamburg, A. V. Tsygankov, M. V. Gerasimenko, O. V. Shishkin, R. I. Zubatyuk, A. V. Mazepa, R. G. Kostyanovsky, “New approach to N,N-dialkoxy-N′-arylureas and N,N-dialkoxycarbamates”, Mendeleev Commun., 21:1 (2011), 50–52
Stephen A. Glover, Patai's Chemistry of Functional Groups, 2010