Angewandte Chemie International Edition in English

Volume 19, Issue 3 pp. 199-201

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Synthesis of Carbocyclic and Heterocyclic π-Electron Systems with Pentafulvenoid Chloroformamidinium Chlorides^†

Prof. Dr. Klaus Hafner,

Prof. Dr. Klaus Hafner

Institut für Organische Chemie der Technischen Hochschule, Petersenstrasse 22, D-6100 Darmstadt (Germany)

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Dipl.-Ing. Hans-Peter Krimmer,

Corresponding Author

Dipl.-Ing. Hans-Peter Krimmer

Institut für Organische Chemie der Technischen Hochschule, Petersenstrasse 22, D-6100 Darmstadt (Germany)

Institut für Organische Chemie der Technischen Hochschule, Petersenstrasse 22, D-6100 Darmstadt (Germany)Search for more papers by this author

Prof. Dr. Klaus Hafner,

Prof. Dr. Klaus Hafner

Institut für Organische Chemie der Technischen Hochschule, Petersenstrasse 22, D-6100 Darmstadt (Germany)

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Dipl.-Ing. Hans-Peter Krimmer,

Corresponding Author

Dipl.-Ing. Hans-Peter Krimmer

Institut für Organische Chemie der Technischen Hochschule, Petersenstrasse 22, D-6100 Darmstadt (Germany)

Institut für Organische Chemie der Technischen Hochschule, Petersenstrasse 22, D-6100 Darmstadt (Germany)Search for more papers by this author

First published: March 1980

https://doi.org/10.1002/anie.198001992

Citations: 9

^†

Dedicated to Professor Matthias Seefelder on the occasion of his 60th birthday

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New key compounds for facile syntheses of unsaturated carbo- and heterocycles are the chloroformamidinium chlorides (2). For example, (2) R = X = H, n = 1, reacts with NH₃ to give (3).

References

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4 K. Hafner, H.-G. Kläs, M. C. Böhm, Tetrahedron Lett. 1980, 41;
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(5) can also be prepared in 75% yield from lithium tert-butylcyclopentadienide and 1,3-dichloro-N,N,N′,N′-tetramethyl-2-azatrimethinecyanine chloride;
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H.-G. Kläs, Diplomarbeit, Technische Hochschule Darmstadt 1979;
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cf. also H.-J. Gais, K. Hafner, Tetrahedron Lett. 1974, 771.
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6(8) is obtained in 28% yield by reaction of the 5-azaazulen-4-one/phosphoryl chloride complex with dimethylamine;
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M. Gold, Dissertation, Technische Hochschule Darmstadt 1979.
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7(1d) is obtained from lithium tert-butylcyclopentadienide by analogy with 6,6-bis(dimethylamino)fulvene ( K. Hafner, G. Schulz, K. Wagner, Justus Liebigs Ann. Chem. 678, 39 (1964)).
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Volume19, Issue3

March 1980

Pages 199-201

Synthesis of Carbocyclic and Heterocyclic π-Electron Systems with Pentafulvenoid Chloroformamidinium Chlorides^†

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Synthesis of Carbocyclic and Heterocyclic π-Electron Systems with Pentafulvenoid Chloroformamidinium Chlorides†

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Synthesis of Carbocyclic and Heterocyclic π-Electron Systems with Pentafulvenoid Chloroformamidinium Chlorides^†