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Avendaño, C.; Menéndez, J. C., Science of Synthesis, (2006) 28, 780.
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 potassium–graphite (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.
Meeeee 88 Meeeeeeee ee Meeeeeeeeeee-8,88-eeeeeeee eeee Meeeee Meeeeeee[88,888]
M8 | M8 | M8 | M8 | Meeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|
Me | Me | M | M | Me | 88 | [88] |
MM=MM | M | M | Me | 88 | [88] | |
M | M | Me | 88 | [88] | ||
M | M | M8M | 88 | [888] |
Me eee eeee ee eee eeeeeeee eeeeeeee 888 e eeeeeeeeeee ee eeeeeeee(M) eeeeeeeeeeeeee eee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eeee ee eeeee eeeee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeeee 888 (Meeeee 88). Meee eee eeeeeee ee eee eeeeeeeeeee eeee ee eeeeeeee ee ee eeeeeee eeeee ee 88% eeee eeeeeeee eee eeeeeeeee ee eee eeeeeee eeeeeeee 888.[8]
Meeeeeeeeeee Meeeeeeee
M,M′-Meeeeeeeeeeeeeeeeeee-8,88-eeeeeee (888, M8 = M8 = Me; M8 = M8 = M):[88]
Me (8 e, 888 eeee) eee eeeee ee eee eeeeee 888 (M8 = M8 = Me; M8 = M8 = M; 8.8 e, 88 eeee) ee MMM (888 eM). Meeee eeeeeeeee eee eeee eee 8 e eeeee M8, ee eee eeeeee ee 88°M eee eeeeeeeee Me eee eeeeeeee eee. Mee M8 eee eeeeeee eeeeeee eee eeee eee 88 eee, eee M8M eee eeee eeeee eeeeee. Mee eeeeeee eee eeeeeeeee eeee Me8M eee eee eeeeeee eee eeeeee eeee M8M (8 × 888 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeeee ee MeMM (888 eM) eee eee eeee eee eeeeee ee −88°M eee 88 e. Mee eeeeeeee eeeeeeee eeee eeeeeeeee; eeeee: 8.8 e (88%).
References
[7] | Meee, M.; Meeeee, M.; Meee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
[10] | Meeeee, M.; Meeee, M. M.; Meeeee, M. M. M.; Meee, M. M.; Meeeeee, M.; Meeeeeee, M. M., Meee. Meee. Meee. Meee-Mee, (8888) 888, 888. |
[120] | Meeeeeee, M.; Meeee, M.; Meeeeeeeee, M., Meeeeeeee, (8888), 888. |