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Synthesis 1995; 1995(7): 759-760
DOI: 10.1055/s-1995-3990
short paper
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1-Aza[2.2]metacyclophane: A Ring Strained Secondary Amine

Dirk Müller, Fritz Vögtle*
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany, Fax +49(228)735662
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Publication Date:
31 December 2000 (online)

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1-Aza[2.2]metacyclophane (1), the hitherto most strained cyclophane with a free NH group in the bridge, is synthesised for the first time with a remarkable yield in the last step by a combination of an intramolecular C-C-coupling reaction and removal of the N-TFA protecting group. The new amine 1 is obtained pure without chromatographic workup, simply by extraction with hydrochloric acid.

Synthesis of the strained title compound 1 by an intramolecular coupling reaction is reported

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