Synthesis 1990; 1990(9): 834-840
DOI: 10.1055/s-1990-27029
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Antiaromatische Verbindungen; 28.1 Eine Synthese von Pyrrol-Derivaten aus Tri-tert-butylazet und Isonitrilen oder Kohlenmonoxid

Udo Hees* , Jürgen Schneider, Oliver Wagner, Manfred Regitz
  • *Fachbereich Chemie der Universität, Erwin-Schrödinger-Straße D-6750 Kaiserslautern, Federal Republic of Germany
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Publication History

Publication Date:
17 September 2002 (online)

Antiaromatic Compounds; 28.1. A Synthesis of Pyrrole Derivatives from Tri-tert-butylazete and Isonitriles or Carbon Monoxide The kinetically stabilized azete 4 reacts with isonitriles 5 in a sequence of [4 + 1] cycloaddition and ring-opening steps to yield 2- and 3-imino substituted 2H- and 3H-pyrrole derivatives 8,9. The α-methylene isonitriles 10 react analogously, but the formation of 2- and 3-iminopyrroles is still followed by an [1,5]-shift which leads to 2- and 3-aminopyrroles 13,14. With carbon monoxide the azete 4 is transformed into the 2H-pyrrole-2-one and 3H-pyrrole-3-one 18 and 19.

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