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N-Tosylaza[2.2]metacyclophan — Darstellung, Struktur, Helicität, Chiroptik, Racemisierung

Vögtle, Fritz ; Przybilla, Klaus-Jürgen ; Mannschreck, Albrecht ; Pustet, Nikola ; Büllesbach, P. ; Reuter, Hans ; Puff, Heinrich


Synthesis, structure, helicity, and chiroptical properties of the ten-membered helical N-tosylaza[2.2]metacyclophane 7a are described for the first time. 7a exist in a strained anti conformation, the inner (Hi-) protons of which absorb at high field (4.13, 4.34 ppm). The enantiomers of 7a were enriched by low-pressure chromatography on triacetylcellulose (TAC). Specific rotations, barrier of racemization, and circular dichrograms are discussed with respect to comparison compounds.

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