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4- und 5-Nitro-benzo[c]thiophen: Reaktionen mit CC-Dienophilen. Synthese von funktionalisierten und anellierten 7-Thia-bicyclo[2.2.1]heptenen — Struktur und Reaktivität voniso-anellierten Systemen mit 4nπ- und (4n+2)π-Elektronen, 19. Mitt.

4- and 5-nitro-benzo[c]thiophene: Reactions with CC dienophiles. Synthesis of functionalized and annelated 7-thia-bicyclo[2.2.1]heptenes — Structure and reactivity ofiso-annelated systems with 4nπ and (4n+2)π electrons XIX

  • Organische Cheme Und Biochemie
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Summary

4- and 5-nitro-benzo[c]thiophenes react as heterocyclic dienes with N-substituted maleic imides. [4+2] cycloaddition gives rise to the formation ofendo, exo configuratedDiels-Alder adducts. This efficient transformation can be utilized for the synthesis of benzo-annelated 7-thiabicyclo[2.2.1]heptenes. Their spectroscopic data are reported and compared with those of the [4 + 2] adducts of isoelectronic 4-(5)-nitro-2-tert-butyl-2H-isoindoles.

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Authors and Affiliations

  1. Lehrstuhl für Organische Chemie II, Fachbereich Chemie der Universität Dortmund, D-44221, Dortmund, Germany

    R. P. Kreher, A. Harpers & F. Wendlandt

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  1. R. P. Kreher
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  2. A. Harpers
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  3. F. Wendlandt
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Kreher, R.P., Harpers, A. & Wendlandt, F. 4- und 5-Nitro-benzo[c]thiophen: Reaktionen mit CC-Dienophilen. Synthese von funktionalisierten und anellierten 7-Thia-bicyclo[2.2.1]heptenen — Struktur und Reaktivität voniso-anellierten Systemen mit 4nπ- und (4n+2)π-Elektronen, 19. Mitt.. Monatsh Chem 128, 271–280 (1997). https://doi.org/10.1007/BF00807893

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