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Stable 1,3‐Oxathiolylium‐4‐olates—Synthesis and Cycloadditions of a Novel Class of Mesoionic Heteroarenes

1982; Wiley; Volume: 21; Issue: 10 Linguagem: Inglês

10.1002/anie.198207791

ISSN

1521-3773

Autores

Hans Gotthardt, Sabine Schoy‐Tribbensee, Ulrich Feist,

Tópico(s)

Fluorine in Organic Chemistry

Resumo

Angewandte Chemie International Edition in EnglishVolume 21, Issue 10 p. 779-779 Communication Stable 1,3-Oxathiolylium-4-olates—Synthesis and Cycloadditions of a Novel Class of Mesoionic Heteroarenes† Prof. Dr. Hans Gotthardt, Corresponding Author Prof. Dr. Hans Gotthardt Lehrstuhl für Organische Chemie der Universität — Gesamthochschule Wuppertal, Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Lehrstuhl für Organische Chemie der Universität, Gesamthochschule Wuppertal Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Search for more papers by this authorSabine Schoy-Tribbensee, Sabine Schoy-Tribbensee Lehrstuhl für Organische Chemie der Universität — Gesamthochschule Wuppertal, Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Search for more papers by this authorUlrich Feist, Ulrich Feist Lehrstuhl für Organische Chemie der Universität — Gesamthochschule Wuppertal, Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Search for more papers by this author Prof. Dr. Hans Gotthardt, Corresponding Author Prof. Dr. Hans Gotthardt Lehrstuhl für Organische Chemie der Universität — Gesamthochschule Wuppertal, Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Lehrstuhl für Organische Chemie der Universität, Gesamthochschule Wuppertal Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Search for more papers by this authorSabine Schoy-Tribbensee, Sabine Schoy-Tribbensee Lehrstuhl für Organische Chemie der Universität — Gesamthochschule Wuppertal, Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Search for more papers by this authorUlrich Feist, Ulrich Feist Lehrstuhl für Organische Chemie der Universität — Gesamthochschule Wuppertal, Gaussstrasse 20, D-5600 Wuppertal 1 (Germany)Search for more papers by this author First published: October 1982 https://doi.org/10.1002/anie.198207791Citations: 5 † This work was supported by the Fonds der Chemischen Industrie. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL No abstract is available for this article. References 1 Mesoionic arenes: W. Baker, W. D. Ollis, Q. Rev. Chem. Soc. 11 (1957)15; M. Ohta, H. Kato in J. P. Snyder: Nonbenzenoid Aromatics, Vol. 1, Academic Press, New York 1969, p. 117; W. D. Ollis, C. A. Ramsden, Adv. Heterocycl. Chem. 19 (1976) 1. 2 2a: M.p. = 103.5–104.5°C (decomp.); IR (CHCl3): 1740, 1633 cm−1 (CO); UV (cyclohexane): λmax (lgϵ)=410 (3.85), 280 nm (4.27); 1H-NMR (90 MHz, CDCl3,TMS): δ = 2.97 (s, SCH3); 19F-NMR (CDCl3, CCl3F): δ = −74.8 (s, CF3). 2b: M.p. = 56–57°C (decomp., petroleum ether); IR (CCl4): 1752, 1640 cm−1 (C = 0); UV (cyclohexane): λmax(lgϵ) = 411 (3.60), 284 (sh, 4.02), 266.5 nm (4.28); 1H-NMR (CCl4): δ=1.78 (s, SC(CH3)3); 19F-NMR (CDCl3): δ = −73.2 (s, CF3). 3(a) H. Gotthardt, C. M. Weisshuhn, Chem. Ber. 111 (1978) 2021; (b) H. Gotthardt, C. M. Weisshuhn, K. Döhöfer, Chem. Ber. 111 (1978) 3336. 4 4: M.p. = 112–112.5°C (cyclohexane); IR (KBr): 1740, 1711, 1702, 1690 cm−1 (CO); 1H-NMR (CCl4): δ = 2.67 (s, SCH3), 3.83 (s, OCH3), 3.91 (s, OCH3). 5 5b: M.p. = 74–76°C(petroleum ether); IR (KBr): 1780, 1728 sh, 1709 cm−1 (C0); 1H-NMR (CCl4): δ = 1.17 (t, J = 7.2 Hz, CH3), 1.56 (s, 3CH3), 2.45, 2.63 (AB of ABX, JAB = 12.8 Hz, CH2), 3.59, 3.69 (2q, J = 7.2 Hz, CH2), 4.33 (X of ABX, JAX = −9.0 Hz, JBx = 3.0 Hz, CH); 13C-NMR (CDCl3): δ = 194.69 (d, J = 5.5 Hz, C0), 182.81 (dq, J = 38.3 Hz, J = 2.5 Hz, CF3–C = O), 114.55 (q, J = 292 Hz, CF3) and additional signals; 19F-NMR (CDCl3): δ = −74.0 (s, CF3). Citing Literature Volume21, Issue10October 1982Pages 779-779 ReferencesRelatedInformation

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