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Journal Article

Synthesis, structure and basicity of 1,16-diaza[6]helicene

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Staab,  Heinz A.
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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Citation

Staab, H. A., Diehm, M., & Krieger, C. (1994). Synthesis, structure and basicity of 1,16-diaza[6]helicene. Tetrahedron Letters, 35(45), 8357-8360. doi:10.1016/S0040-4039(00)74406-6.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0019-A8B0-F
Abstract
The extension of 'proton sponges' 1 and 2 by further anellation to 1,16-diaza[6]helicene (3) was of interest to define scope and limitation of 'proton sponge' properties. 3 was prepared by photocyclisation of 2,7-bis(3-pyridylvinyl)naphthalene 4 and by Pd-catalyzed aryl-aryl coupling of the corresponding tetrabromo derivative 7. As consequence of the helical structure, 3 does not show 'proton sponge' basicity. X-ray structure analyses of 3 and 3·2HBr are in accordance with these findings.