Synthesen und chemisches Reaktionsverhalten neuer überbrückter Chinonderivate. Kupplungsreaktionen von Diazoniumsalzen mit 2‐Methoxy‐1,6‐methano [10]annulen

Syntheses and Chemical Properties of New Bridged Quinone Derivatives. Coupling Reactions of Aryldiazonium Salts with 2‐Methoxy‐1,6‐methano[10]annulene Coupling of 2‐methoxy‐1,6‐methano[10]annulene (3) with the aryldiazonium salts 4a‐4i yields the quinone hydrazones 5a‐5i. The spectroscopic properties of these products are described. The reaction of 3 with 4‐nitrophenyldiazonium tetrafluoroborate buffered with sodium acetate in dry methanol yielded after chromatographic separation the azo derivative 7 on the one hand and a mixture of the valence tautomers 8a and 8b on the other.