caa a22 4500 475759745 CHVBK 20180406123547.0 cr unu---uuuuu 170329e20000701xx s 000 0 eng 10.1007/BF02495762 doi (NATIONALLICENCE)springer-10.1007/BF02495762 Generation of diazo-2-methylenecyclopropane and its 1,3-dipolar cycloaddition to acrylates [Elektronische Daten] [Yu. Tomilov, I. Klimenko, E. Shulishov, O. Nefedov] N-(2-Methylenecyclopropyl)-N-nitrosourea (2) was synthesized for the first time (yield 70%) and its decomposition induced by bases was studied. In particular, treatment with MeONa/MeOH at-30°C in the presence of methyl methacrylate gives the corresponding I-pyrazoline stereoisomers, the products of [3+2]-cycloaddition of diazo-2-methylene-cyclopropane (1) generatedin situ. Decomposition of2 on treatment with K2CO3 at 0-5°C in the presence of acrylonitrile also proceeds as [3+2]-cycloaddition: however, the expected 2-pyrazoline easily isomerizes into 5(3)-isopropenyl-3(5)-cyanopyrazole. Buta1,2,3-triene is the main product of base-induced decomosition of2 in the absence of unsaturated substrates. Kluwer Academic/Plenum Publishers, 2000 diazo-2-methylenecyclopropane nationallicence spiro(1- and 2-pyrazoline-5,1′-cyclopropanes) nationallicence cyanopyrazoles nationallicence buta-1,2,3-triene nationallicence cyclopropylidenes nationallicence 1,3-dipolar cycloaddition nationallicence NMR nationallicence Tomilov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Klimenko 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 Nefedov O. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/7(2000-07-01), 1207-1211 1066-5285 49:7<1207 2000 49 11172 https://doi.org/10.1007/BF02495762 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495762 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- Klimenko 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- Nefedov O. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/7(2000-07-01), 1207-1211 1066-5285 49:7<1207 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer