4,5‐Bis(dimethylamino)phenanthrene and 
4,5‐Bis(dimethylamino)‐9,10‐dihydrophenanthrene: Syntheses and “Proton Sponge” 
Properties

Saupe, Thomas; Krieger, Claus; Staab, Heinz A.

doi:10.1002/anie.198604511

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4,5‐Bis(dimethylamino)phenanthrene and 4,5‐Bis(dimethylamino)‐9,10‐dihydrophenanthrene: Syntheses and “Proton Sponge” Properties

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Saupe, Thomas
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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Staab, Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.198604511
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Citation

Saupe, T., Krieger, C., & Staab, H. A. (1986). 4,5‐Bis(dimethylamino)phenanthrene and 4,5‐Bis(dimethylamino)‐9,10‐dihydrophenanthrene: Syntheses and “Proton Sponge” Properties. Angewandte Chemie International Edition, 25(5), 451-453. doi:10.1002/anie.198604511.

Cite as: https://hdl.handle.net/21.11116/0000-0006-9178-F

Abstract

Strong, almost linear N ċ H ċ N hydrogen bonds are present in 1 ‐perchlorate and its 9,10‐dihydro derivative. The N ċ N distance is even shorter and the H/CH3 bridge coupling stronger than in the analogue with a fluorene skeleton. Unprotonated 1 could be generated via a dichlorinated seven‐membered dibenzosulfone.