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Tobe, Y.; Takeda, T., Science of Synthesis, (2010) 45, 1318.
[3.2]Paracyclophanenes 41 and [3.2.3.2]paracyclophanedienes 42 are prepared by intramolecular and intermolecular McMurry coupling, respectively, of the diketone precursors 40.[20] By changing the conditions, the intra- and intermolecular coupling products are produced selectively (Scheme 7).
Meeeee 8 Meeeeeeee ee Meeeeeeeee-Meeeeee Meeeeeeeeeeeeee ee MeMeeee Meeeeeee[88]
| M8 | Meeeeeeeee | Meeee (%) | Mee | 88 | 88 |
|---|---|---|---|---|
| Me | eeeeeeeee eeeeeeee eeee 88 e, eeee eeeeee, 88 e | 88 | – | [88] |
| eeeeeeeee eeeeeeee eeee 88 e | – | 88 | [88] | |
| Me | eeeeeeeee eeeeeeee eeee 88 e, eeee eeeeee, 88 e | 88 | – | [88] |
| eeeeeeeee eeeeeeee eeee 88 e | – | 88 | [88] |
MeMeeee eeeeeeee ee eeeeeeeeee 88, eeeeeeee eeeeee ee eeeeee Meeeee eeeeeeee ee eeeeeeeeeeeeeeeeee eeee eee(eeeeeeeeeee) eeee 88 (ee. Meeeee 8, Meeeeee 88.88.8.8.8.8), eeeee [8.8.8]eeeeeeeeeeeeeeeeeeee 88 ee 88% eeeee.[88] Me eeeeeeeee eee eeeeeeeeee, e.e. eeeeeeee, eee eeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee eeeeeee 88 eee eeeeeee eeeeeee 88 eeeeee ee eeeeeeeeeeeeee eeeeeeee eee ee eeeeeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee Meeee Meeeeeeeee Meeeee-8,8-eeee-Meeeeee Meeeeeeeeeeeeee ee MeMeeee Meeeeeee[88,88]
| Meeeeee | Meeee (%) | Mee | 88 | 88 |
|---|---|---|---|
| MMM | 88 | – | [88] |
| MMM | 88 | 88 | [88] |
| MMM/eeeeeee (8:8) | 88 | 88 | [88] |
| MMM/eeeeeee (8:8) | 8 | 88 | [88] |
| MMM/eeeeeee (8:8) | 8 | 88 | [88] |
| MMM/eeeeeee (8:8) | eeeee | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
8,8,8(8,8)-Meeeeeeeeeeeeeeeeeeeeeee-8,8,8-eeeeee (88):[88]
MeMe8 (8.8 eM, 88 eeee) eee eeeee eeee eeeeeeee eeeee eeeee ee eeeee MMM (888 eM) ee 8°M. Me eeeeee (8.88 e, 88 eeee) eee eeee eeeee eeeeeeeee ee eeeee eeeeeeee, eeeeeeee ee eeeee eeeeeeee (ee. 8 eM). Mee eeeeeeeee eeeee eeeeeee eee eeeeeeee eee 8 e eeeeee eeeeeeee eeeeeeee ee e eeee ee eeeeeeeeee 88 (8.88 e, 8 eeee) ee MMM (88 eM) eeee eeeeeee eeeee. Mee eeeeeeeee eeeeeee eee eeee ee eeeeee eeeee MMM eeeeeeeee eeeeeeee eeeeeeeeeeeee ee eeeeeeee eeeeeeee, eeeeee ee 8°M, eee eeeeeeee ee eeee eeeeeeee ee 88% M8MM8 eeee. Mee eeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeee eeeeeeee eee eeeeee eeee eeee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eee eee eeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (MM8Me8) ee eeee eeee eeeeee eeeeeeee. Meeeeeeeeee ee eeee eeeeeeee eeeeeee eeeeeeeee eeeeeeee; eeeee: 88 e (88%); ee 888–888°M.
References
| [20] | Meüeeeeeeee, M.-M.; Meeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [21] | Meeeee, M.; Meeeeeeeeöe, M.; Meeeeeee, M., Müeeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [22] | Meeeee, M.; Meee, M.; Meeeee, M.; Meeeee, M.; Mee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
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