Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle"

Funke U, Grützmacher H-F (1989)
Chemische Berichte 122(8): 1503-1508.

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4,4-Dimethyl-1,2-bis(4-methylphenyl)-3,5-pyrazolidinedione (4), 1,2-bis(4-methylphenyl)perhydro-3,6-pyridazinedione (5), and 1,2-bis(4-methylphenyl)perhydro-3,7-diazepinedione (6) have been prepared by condensation of p-hydrazotoluene with the appropriate dicarbonyl dichlorides and then converted into the corresponding bis(bromomethyl) derivatives 7-9 by photobromination. 7-9 have been tested as starting compounds for the synthesis of 2-thia-10,11-diaza[3.2]paracyclophan-10-ene (2) and 2,5-dithia-13,14-diaza[6.2]paracyclophan-13-ene (3). In no case 2 has been obtained, independent of the ring size and conformation of 7-9. However, 3 was readily formed from all precursors; the dimethylmalonyl moiety proved to be convenient as a protecting group because of its ease of preparation, its stability, and its facile cleavage by alkali.
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Funke U, Grützmacher H-F. Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle". Chemische Berichte. 1989;122(8):1503-1508.
Funke, U., & Grützmacher, H. - F. (1989). Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle". Chemische Berichte, 122(8), 1503-1508.
Funke, U., and Grützmacher, H. - F. (1989). Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle". Chemische Berichte 122, 1503-1508.
Funke, U., & Grützmacher, H.-F., 1989. Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle". Chemische Berichte, 122(8), p 1503-1508.
U. Funke and H.-F. Grützmacher, “Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle"”, Chemische Berichte, vol. 122, 1989, pp. 1503-1508.
Funke, U., Grützmacher, H.-F.: Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle". Chemische Berichte. 122, 1503-1508 (1989).
Funke, Ulrike, and Grützmacher, Hans-Friedrich. “Schutzgruppen zur Synthese von Diaza-cyclophanen nach dem "Rigid-Group-Principle"”. Chemische Berichte 122.8 (1989): 1503-1508.
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