Benzo[c ]benzo[3,4]cinnolino[1,2‐a ]cinnoline, a Chiral Hydrazine Derivative

Fischer, Hans; Krieger, Claus; Neugebauer, Franz A.

doi:10.1002/anie.198603741

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Benzo[c ]benzo[3,4]cinnolino[1,2‐a ]cinnoline, a Chiral Hydrazine Derivative

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Fischer, Hans
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger, Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Neugebauer, Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Fischer, H., Krieger, C., & Neugebauer, F. A. (1986). Benzo[c ]benzo[3,4]cinnolino[1,2‐a ]cinnoline, a Chiral Hydrazine Derivative. Angewandte Chemie International Edition, 25(4), 374-375. doi:10.1002/anie.198603741.

Cite as: https://hdl.handle.net/21.11116/0000-0006-90B7-8

Abstract

The spontaneous crystallization of the enantiomers of the title compound 1 (space group P 21) has been observed. The X‐ray structure analysis reveals a pyramidal arrangement of the substituents on the nitrogen atoms. The large barrier to racemization (27.1 kcal mol−1) is largely due to the gauche effect of the vicinal lone pairs of electrons.