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

✍ Scribed by Richard Neidlein; Christoph Martin Radke

• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: German
• Weight: 439 KB
• Volume: 66
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19830660749

✦ Synopsis

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.