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28.10.3.1.1.2 Method 2: Metal-Induced Oxidative Intramolecular Aryl–Aryl Coupling

DOI: 10.1055/sos-SD-028-00690

Avendaño, C.; Menéndez, J. C.Science of Synthesis, (200628780.

Symmetrically or unsymmetrically substituted phenanthrene-9,10-diimines 161 are prepared by the alkaline metal mediated cyclodehydrogenations of aromatic open-chain diimines 160, which are available from 1,2-diphenylethanes (Scheme 55). Several alkaline metals can be employed, the most successful being lithium[‌10‌] or potassiumgraphite (the latter combination is preferable to potassium or sodium alone).[‌120‌] In both cases, the reaction appears to occur by a thermal electrocyclic reaction of the appropriate dianion.

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