caa a22 4500 475762258 CHVBK 20180406123554.0 cr unu---uuuuu 170329e20001101xx s 000 0 eng 10.1007/BF02494938 doi (NATIONALLICENCE)springer-10.1007/BF02494938 Different reactivities of regioisomeric azimines, adducts of phthalimidonitrene with 5-bromospiro[1-pyrazoline-3,1′-cyclopropane] [Elektronische Daten] [Yu. Tomilov, I. Kostyuchenko, E. Shulishov, B. Averkiev, M. Antipin] The addition of the phthalimidonitrene fragment, resulting from oxidation ofN-aminophthalimide by lead tetraacetate at −20 to −30°C, to the N=N-bond of 5-bromospirol[l-pyrazolinio-3,1′-cyclopropane] (1) affords, apart from the stable 5-bromo-N {spiro[l-pyrazolinio-3,1′-cyclopropane]}-N-phthalimidoamide (azimine2), regioisomeric azimine3, which is completely transformed into 3-acetoxy-N-{spiro[l-pyrazolinio-5,1′-cyclopropane]}-N-phthalimidoamide (4) under the reaction conditions. The acetoxy group in this product easily undergoes nuclcophilic substitution on treatment with McOH, NaN3, or the starting bromopyrazoline1. The structures of azimines obtained were established using NMR spectra, and the structure of the product of reaction of4 with1 was additionally proved by X-ray difraction data. Kluwer Academic/Plenum Publishers, 2000 5-hromospiro[l-pyrazoline-3,1′-cyclopropane] nationallicence 3-substituted N -{spiro[l-pyrazolinio-5,1′-cyclopropane]}- N -phthalimidoamides (azimines) nationallicence nuclcophilic substitution nationallicence NMR spectra nationallicence X-ray diffraction analysis nationallicence Tomilov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Kostyuchenko I. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Shulishov E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Averkiev B. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Antipin M. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/11(2000-11-01), 1919-1922 1066-5285 49:11<1919 2000 49 11172 https://doi.org/10.1007/BF02494938 text/html Onlinezugriff via DOI 1 brief-communication jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02494938 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Tomilov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Kostyuchenko I. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Shulishov E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Averkiev B. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Antipin M. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/11(2000-11-01), 1919-1922 1066-5285 49:11<1919 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer