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Volumn 53, Issue 12, 2014, Pages 3158-3162

Transition from π radicals to σ radicals: Substituent-tuned cyclization of hydrazonyl radicals

Author keywords

alkenes; cyclization; heterocycles; radicals; synthetic methods

Indexed keywords

ATOMS; ELECTRONIC STRUCTURE; OLEFINS;

EID: 84896383491     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309918     Document Type: Article
Times cited : (92)

References (36)
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    • Such 5-exo-trig cyclizations of hydrazonyl π radicals have also been reported recently by another research group.
    • Such 5-exo-trig cyclizations of hydrazonyl π radicals have also been reported recently by another research group:, M.-K. Zhu, Y.-C. Chen, T.-P. Loh, Chem. Eur. J. 2013, 19, 5250.
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    • Radical cations of hydrazones with a σ-electronic structure have been reported
    • Radical cations of hydrazones with a σ-electronic structure have been reported:, A. Berndt, R. Bolze, R. Schnaut, H. Woynar, Angew. Chem. 1981, 93, 400
    • (1981) Angew. Chem. , vol.93 , pp. 400
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    • however, no neutral hydrazonyl radicals with a σ-electronic structure have yet been reported.
    • Angew. Chem. Int. Ed. Engl. 1981, 20, 390; however, no neutral hydrazonyl radicals with a σ-electronic structure have yet been reported.
    • (1981) Angew. Chem. Int. Ed. Engl. , vol.20 , pp. 390
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    • radicals have also been described as radicals in which the spin-bearing orbital is orthogonal to an adjacent π system; see
    • W. C. Danen, C. T. West, J. Am. Chem. Soc. 1973, 95, 6872; σ radicals have also been described as radicals in which the spin-bearing orbital is orthogonal to an adjacent π system; see
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6872
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    • for the transition-metal-catalyzed vicinal aminooxygenation of olefins, see
    • Angew. Chem. Int. Ed. 2012, 51, 3462; for the transition-metal-catalyzed vicinal aminooxygenation of olefins, see
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    • CCDC 968882 (2 j), 968883 (2 k), 968884 (2 t), and 968885 (3 u) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 968882 (2 j), 968883 (2 k), 968884 (2 t), and 968885 (3 u) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • For a 1,5-H shift involving a hydrazonyl radical, see.
    • For a 1,5-H shift involving a hydrazonyl radical, see:, X. Zhu, Y.-F. Wang, W. Ren, F.-L. Zhang, S. Chiba, Org. Lett. 2013, 15, 3214.
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    • Azomethine Imines": in (Eds.: A. Padwa, D. Bellus), Thieme, Stuttgart
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    • A similar dichotomy has been reported for the nucleophilic addition of hydrazides to alkynes; in these reactions, both nitrogen atoms could be activated in a controllable manner.
    • A similar dichotomy has been reported for the nucleophilic addition of hydrazides to alkynes; in these reactions, both nitrogen atoms could be activated in a controllable manner:, S. F. Vasilevsky, T. F. Mikhailovskaya, V. I. Mamatyuk, G. E. Salnikov, G. A. Bogdanchikov, M. Manoharan, I. V. Alabugin, J. Org. Chem. 2009, 74, 8106.
    • (2009) J. Org. Chem. , vol.74 , pp. 8106
    • Vasilevsky, S.F.1    Mikhailovskaya, T.F.2    Mamatyuk, V.I.3    Salnikov, G.E.4    Bogdanchikov, G.A.5    Manoharan, M.6    Alabugin, I.V.7


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