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R. Reinhard, M. Glaser, and Neumann, G. Maas (1997)
Tri- and Tetracyclic Azepine Derivatives by Thermally Induced Cyclization of Aminoallenes and Semicyclic 2-DienaminesJournal of Organic Chemistry, 62
D. Enders, K. Breuer, Ulrike Kallfass, Tim Balensiefer (2003)
Preparation and Application of 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene, A Stable CarbeneSynthesis, 2003
Zixian Chen, Jiangtao Zhu, Haibo Xie, Shan Li, Yong-ming Wu, Y. Gong (2011)
A cascade process for the synthesis of gem-difluoromethylene compounds.Organic & biomolecular chemistry, 9 10
N. Nedolya, B. Trofimov (2013)
[1,7]-Electrocyclization reactions in the synthesis of azepine derivativesChemistry of Heterocyclic Compounds, 49
Sigrid Espenlaub, H. Gerster, G. Maas (2007)
Synthesis and reactivity of 3-(dialkylamino)allenyl phosphonium salts. PPh3-mediated synthesis of pyrroles from propyne iminium triflatesArkivoc, 2007
M. Reisser, G. Maas (2004)
Synthesis of pyrroles from 1-dialkylamino-3-phosphoryl(or phosphanyl)allenes through 1,5-cyclization of conjugated azomethine ylide intermediates.The Journal of organic chemistry, 69 15
Supplementary Material: The online version of this article offers supplementary material
S. Hitzel, Christian Färber, C. Bruhn, U. Siemeling (2014)
Reactions of [RuCl2(PPh3)3] with Nitron and with the “Enders Carbene”: Access to Ruthenium(III) NHC ComplexesOrganometallics, 33
Jian Cao, Xiongfa Yang, X. Hua, Yuan Deng, G. Lai (2011)
Synthesis of 2-azaanthracenes via a sequential Sonogashira coupling/alkynyl imine-allenyl imine isomerization/aza-Diels-Alder/elimination-aromatization reaction.Organic letters, 13 3
Prepared from propyne imine 4b (229 mg, 1.00 mmol) and Nitron (630 mg, 2.02 mmol)
T. Schneider, Bianca Seitz, Maximilian Schiwek, G. Maas (2020)
1-Fluoroalkyl-prop-2-yne 1-imines and 1-iminium salts as building blocks: A new synthesis of α-(trifluoromethyl)pyrrolesJournal of Fluorine Chemistry, 235
A. Simas, Joseph Miller, P. Filho (1998)
Are mesoionic compounds aromaticCanadian Journal of Chemistry, 76
G. Olah (1961)
Deuterofluoboric acid and nitron deuterotetrafluoroborate: The structure of nitron saltsJournal of Inorganic and Nuclear Chemistry, 16
101 MHz): δ = 64.81 (NCH 2 ), 89.96 (C spiro ), 114.29, 117.40, 119.06 (q, 1 J C,F = 276.2 Hz, CF 3 )
M. Busch
Ueber Endimino-triazoleEuropean Journal of Inorganic Chemistry, 38
Peter Johnson, J. Renga, C. Galliford, G. Whiteker, Natalie Giampietro (2015)
Synthesis of Novel Fluoropicolinate Herbicides by Cascade Cyclization of Fluoroalkyl Alkynylimines.Organic letters, 17 12
Jia‐Rong Chen, Xiao-Qiang Hu, Liang‐Qiu Lu, W. Xiao (2015)
Formal [4+1] annulation reactions in the synthesis of carbocyclic and heterocyclic systems.Chemical reviews, 115 11
An HPLC separation of the mother liquor (eluent: cyclohexane-EtOAc (5:1)) afforded pyrrole 8, which was further purified by recrystallization from cold n-pentane (30 mg, 0.053 mmol, 3%)
T. Schneider, Michael Keim, Bianca Seitz, G. Maas (2020)
Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenesBeilstein Journal of Organic Chemistry, 16
W. Baker, W. Ollis (2022)
Meso-ionic compoundsAdvances in Heterocyclic Chemistry
752 (m), 691 (m). − 1 H NMR (CDCl 3 , 400 MHz): δ = 6.33 (s, 1H), 6.50 (s, 1H)
42 (s, 1H, CH olefin )
90 (q, 1 J C,F = 279.2 Hz
Purification by recrystallization from CH 2 Cl 2 -n-pentane. Red-brown solid (223 mg, 0.39 mmol, 20%), m.p. 116
J. Grant, Zhou Lu, D. Tucker, Bryony Hockin, D. Yufit, M. Fox, R. Kataky, V. Chechik, A. O’Donoghue (2017)
New Blatter-type radicals from a bench-stable carbeneNature Communications, 8
(2001)
The Merck Index: An Encyclopaedia of Chemicals, Drugs and Biologicals, 13th ed.; Merck & Co., Inc.: Whitehouse Station
Ar -F and C(CF 3 )=N signals appear to conincide). -19 F NMR (CDCl 3 ): δ = −69.03 (CF 3 ), −110.28 (C Ar F). − HRMS (MALDI): m/z = 541.18875
62 (d, 1 J C,F = 253.1 Hz, C Ar F). -19 F NMR (CDCl 3 ): δ = −59
400 MHz): δ = 6.28 (s, 1H), 6.52 (s, 1H)
Charlotte Thie, S. Hitzel, L. Wallbaum, C. Bruhn, U. Siemeling (2016)
Coinage metal complexes of the carbenic tautomer of NitronJournal of Organometallic Chemistry, 821
C. Ramsden, W. Oziminski (2015)
The relative stability of mesoionic and N-heterocyclic carbene tautomers: a computational study of substituent effectsTetrahedron, 71
D. Enders, K. Breuer, G. Raabe, J. Runsink, J. Teles, Johann‐Peter Melder, K. Ebel, S. Brode (1995)
Preparation, Structure, and Reactivity of 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene, a New Stable Carbene†Angewandte Chemie, 34
M. Busch
Gravimetrische Bestimmung der SalpetersäureEuropean Journal of Inorganic Chemistry, 38
20 (d, 3 J H,H = 8.8 Hz, 2H, CH NO2Ph ). − 13 C{ 1 H} NMR (CDCl 3 , 101 MHz): δ = 31
D. Enders, K. Breuer, J. Runsink, J. Teles (1996)
Chemical Reactions of the Stable Carbene 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylideneLiebigs Annalen, 1996
AbstractThe heterocyclic mesoionic compound (1,4-diphenyl-1H-1,2,4-triazol-4-ium-3-yl)(phenyl)amide („Nitron“) has recently been found to exist in a prototropic equilibrium with minor amounts of a nucleophilic heterocyclic carbene of the 1,2,4-triazolyl-5-ylidene type. Here we report that Nitron reacts with 1-trifluoromethyl-substituted prop-2-yne iminium salts by conjugate nucleophilic addition of the anionic PhN‒ substituent in the mesoionic tautomer, whereas the nucleophilic triazolylidene form is involved in the reaction with 1-CF3-prop-2-yne imines. 3-(2,3-Dihydro-1H-benzo[c]azepin-5-yl)-1H-1,2,4-triazol-4-ium triflate salts were obtained in the former case and (Z)-9-arylidene-1,2,4,7-tetraazaspiro[4.4]nona-2,7-dienes in the latter.
Zeitschrift für Naturforschung B – de Gruyter
Published: Dec 16, 2020
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