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., 2006, Volume 16, Issue 6,Pages 323

This article is cited in 23 papers

N-Chloro-N-alkoxyureas: synthesis, structure and properties

V. G. Shtamburg^a, O. V. Shishkin^b, R. I. Zubatyuk^b, S. V. Kravchenko^a, A. V. Tsygankov^a, A. V. Mazepa^c, E. A. Klots^d, R. G. Kostyanovsky^e

^a Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, Ukraine
^b STC 'Institute for Single Crystals', National Academy of Sciences of Ukraine, Kharkov, Ukraine
^c A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine
^d Kirovograd State Pedagogical University, Kirovograd, Ukraine
^e N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: 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 n_O–^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.

Language: English

DOI: 10.1070/MC2006v016n06ABEH002382