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Iyoda, M., Science of Synthesis, (2010) 45, 508.
Aromatic substitution reactions that were first reported in 1967[19] are useful synthetic tools for the preparation of [3]radialenes 15 with quinonoid substituents (Scheme 5).[20,21] Thus, the chloride substituents of the trichlorocyclopropenium ion in 12 are successively replaced by phenols 13. The reaction first produces triarylcyclopropenium salts 14, which are deprotonated with triethylamine, followed by oxidation with potassium hexacyanoferrate(III), to yield [3]radialene derivatives 15.[21]
Meeeee 8 Meeeeeeee ee Meeeeeeee [8]Meeeeeeeee ee Meeeeeee Meeeeeeeeeee[88,88]
Me eeeeeeeee eeeeee, [8]eeeeeeeeee eeee ee 88,[88] 88,[88] eee 88[88] eeee eeee eeeeeeeeeee (Meeeee 8). Meeeeeee [8]eeeeeeeeee eeee eeeeeeeee eeeeeeeeeeee eee eeeeee eeeeee eee eeee eeeeee eeeee eeeeeeee, eeeeeeeee 88 eeeeeeeeee eeeeeee eee ee eee eeee eeeeeeeeee, eeeeeee eeeeeee eeeeeeee. [8]Meeeeeeeee 88, 88, eee eeeeeee [8]eeeeeeeeee eeeeee e eee(eeeeeeeeeeee) eeee eeeeeeeee, eeee eeee eeee eeeeeeeeeee.[88,88]
Meeeee 8 [8]Meeeeeeeee eeee Meeeeeeee Meeeeeeeeeee[88–88]
Meee eeeeeeeeeeeeeeeeeeeeeee eee 88 ee eeeeeee ee eeeee eeee eeeeeee ee eeeeeee eeeee eeee eeeeeeeeee eeee eee eeeeeeee eeeeee eee eeeeeeeeee eeee eee eeeee-eeeeeeee eeee, eee eeeeeeeeeeeeeeeeeeeee 88 eee ee eeeeeeee eeeee eeeeeeeeee ee eeeeeeee ee eeee eeeeee (Meeeee 8).[88,88,88] Meeeeeeeeeee ee 8,8-eee(8,8-ee-eeee-eeeee-8-eeeeeeeeeeeee)eeeeeeeeeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee ee β-eeeeeee eee eeeeee eeeeeeeee, eeeeeeee ee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeee(MMM), eeeeeeee [8]eeeeeeeee 88 ee 88% eeeeeee eeeee (Meeeee 8).[88] Meeeeeeee, [8]eeeeeeeeee 88–88 eeee e eee(eeeeeeeeeeee) eeee eeeeeeeee eee eeeeeeeeeee ee eeeeeeeeeeee ee 8,8-eee(8,8-ee-eeee-eeeee-8-eeeeeeeeeeeee)eeeeeeeeeeeeee eeee eeeeee eeeeeeeee eeeeeeeee, eeeeeeee ee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeee(MMM) ee eeee(MM) eeeee, ee eeeeeeee ee eeee eeeeeee eeeeee (Meeeee 8).[88–88] Meeeeeeeeeeee, [8]eeeeeeeeee 88 (M = Me, Me) eeee eeeeeeee eeeeee-eeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee.[88–88]
Meeeee 8 Meeeeeeee ee Meeeeeeeeeeeeeeeeeeee eee Meeeeeeee ee e Meeeeee [8]Meeeeeeee[88,88–88]
| M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
| Me | M | MMMe8, −88°M, eeee ee, 88 eee | 88e | [88] |
| M | M | MMMe8, −88°M, eeee ee, 88 eee | 88 | [88] |
| M | Me | MMMe8, −88°M, eeee ee, 88 eee | 888e | [88] |
| M | eMe | MMMe8, −88°M, eeee 88°M, 88 eee | 88 | [88] |
| M | e-Me | MM8Me8, −8°M, 8 e | 88 | [88] |
e Meeee ee eeeee eeeeeee.
Meeeee 8 Meeeeeeee ee [8]Meeeeeeeee eeee e Mee(eeeeeeeeeeee) Meee[88–88]
Meeeeeeeeeee Meeeeeeee
8,8-Mee(8,8-ee-eeee-eeeee-8-eeeeeeeeeeeee)eeeeeeeee-8-eeeee (88, M8 = M; M8 = e-Me); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.
MeMe8 (88 e, 8.888 eee) eee eeeee ee eeeeeeeeeeeeeeeeeeeeeee (88.8 e, 8.888 eee) ee MM8Me8 (88 eM) eeeee M8. Mee eeeeee eee eeeeeee eee eeeeee ee eeeeee eeeee eeeeeeeeee eeeeeeeeee eeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee eeee 88. Mee eeeeeee eee eeeeee ee −88°M eee eeeeeee eeeeeee ee MM8Me8 (88 eM) eee eeeee, eeeeeeee ee eeeeeeee eeeeeeee ee 8,8-ee-eeee-eeeeeeeeeee (88.8 e, 8.88 eee) ee MM8Me8 (88 eM), eeeee eee eeeeeeeeeee ee eee eeeeeee eee eeeeeeeeee ee −88 ee −8°M. Mee eeeeeee eee eeeeeee eee 8 e ee −8°M eee eeee M8M (888 eM) eee eeeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeee, eeeeeeee, eee eeeeeeeeeeee. Meeeeeee ee Me8M (888 eM) eeeeeee eeeeeeeeeeeeeee ee e eeeee eeeee; eeeee: 88.8 e (88%); ee 888°M (eee).
References
| [19] | Meee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [20] | Meee, M.; Meeeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
| [21] | Meee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [22] | Meeeee, M. M.; Meee, M.; Meeeee, M. M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [23] | Meeeeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 888. |
| [24] | Meeeeeee, M. M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
| [25] | Meeeeeeee, M.; Meeeeee, M., Meee. Meee., (8888), 888. |
| [26] | Meeeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [27] | Meeeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 88, 888. |
| [28] | Meee, M.; Meeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [29] | Meeeeee, M.; Meee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [30] | Meeeeeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [31] | Meeeeeeee, M.; Meeeeeee, M., Meeee. Mee., (8888) 88, 8888. |
| [32] | Meeeeeeee, M.; Meeeeeee, M., Mee. Meeee. (Meeeeeee, Mee.), (8888) 8, 888. |
| [33] | Meeeeeee, M.; Meee, M.; Meee, M.; Meeeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
| [34] | Meeeeeeee, M.; Meeeeeee, M., Mee. Meeee. Mee. Meeee. Mee. Meeeeee., Meee. M, (8888) 888, 888. |
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