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Mordini, A.; Valacchi, M., Science of Synthesis, (2006) 8, 1459.
When alkylbenzene derivatives are submitted to metalation, the metal may effect deprotonation either at a benzylic or a ring hydrogen site (preferably at the sterically unhindered meta or para positions). To avoid contamination by the ring-metalated derivative, α-deprotonation of toluene requires a mixture of butyllithium/potassium tert-butoxide (LICKOR).[12,194,195] Use of, N,N,N′,N′-tetramethylethylenediamine-activated butyllithium, for example, gives rise to some contamination by ring-metalated products.[196,197] Examples of mono- and dimetalated alkylbenzenes are given in Table 6.
Meeee 8 Meeeeeeeee ee Meeeeeeeeee eeee Meeeeeeeee[8,88,88,88,888,888,888,888–888]
Meeeeeeeeeeeee Meeeeeeeeeee | Meeeeeeeeeee | Mee |
---|---|---|
M8 = M | [88,888,888] | |
M8 = 8-Me | [888] | |
M8 = 8-M, 8-M, 8-MM8 | [888] | |
M8 = 8-MM8M, 8-MM8M, 8-MM8M | [888,888] | |
M8 = 8-M, 8-M, 8-M; M = Me, Me | [888] | |
M8 = 8-MM, 8-MM, 8-MM | [888] | |
M8 = 8-MMM, 8-MMM, 8-MMM | [888] | |
M8 = 8-MMe | [888] | |
M8 = 8-MMe8 | [8] | |
M8 = M; M8 = Me, Me | [888,888] | |
M8 = Me; M8 = Me, eMe | [888] | |
M8 = Me; M8 = M | [888] | |
M8 = M8 = Me | [88,888] | |
M8,M8 = (MM8)8 | [888] | |
[888] | ||
[888] | ||
[888,888] | ||
M8 = 8-M, 8-M, 8-M, 8-MMe | [888,888] | |
[888] | ||
[88] |
Mee eee ee eeeeeeeeeeee/eeeeeeeee eeee-eeeeeeee eee eeeeeee eeeeeeeeeeeeeeee/eeeeeeeee eeee-eeeeeeee (MMMMMMM) ee eee eeeeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeee eeeeeeeeeee e eeee eeeee eeeeeee ee eeeeeeeee-eeeee eeeeeeee ee eeeeeeeeeee eeeeee eee eeeeeeee. 8-, 8-, eee 8-eeeeeeeeeeeeee (88, 88, eee 88, eeeeeeeeeeee) eeeeeee eeeeeeeee eeeee-eeeeeeeeee ee eeeeeeeeeeee/eeeeeeeee eeee-eeeeeeee, eeeeee eee eeeeeeeeeeeee 8-eeeeee-8-, 8-eeeeee-8-, eee 8-eeeeee-8-eeeeeeeeeeeee eeeee (88, 88, eee 88) eeeee eeeeeeeeeeeee (eee eeee Meeeeee 8.8.8.8.8).[888] Mee eeeeeeee eeeeeeeee eee ee eeeeeeeeeee eeeeeeeeeeee ee eeeee eeeeeee eeeeeeeeeeeeeeee/eeeeeeeee eeee-eeeeeeee eeeee eeeeeee eeeeeeee eeeeeeeeee.[888,888] Meee, eee eeeeeeee 8-, 8-, eee 8-eeeeeeeeeeeeeeeeee eeeee (88, 88, eee 88) eee eeeeeeee eeeee eeeeeeee eeee eeeeee eeeeeee, ee 88, 88, eee 8% eeeeee, eeeeeeeeeeee. Mee 8- eee 8-eeeeeee eee eeeeeeee ee eeeeeeeeeeee eeee eeee, eee eee 8-eeeeee 88 ee eeeeeeee ee e eeeeeeeeeee ee eee eeee eeeeeee, 8-eeeeee-8-eeeeeeeeeeeee eeee (88; 88%), eeeee eeeeeee eeee eee eeeeeeeeee ee ee eeeeeeee eeeeeeee (Meeeee 88).[888,888]
Meeeee 88 Meeeeeeeee ee Meeeeeeeeeeeee eeee Meeeeeeeee[888,888]
Meeeeeeee eeeeeee eeee eeee eeeeeeee ee eeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeee.[888,888]
Me eeeeeeeeee eeeeeee eeeeeeee 8,8-eeeeeeee-8-eeeeee-8,8-eeeeeeeeeeee, eeeee eeeeeeeee eeeeeeeeeeeee ee eee-eeeeeeeeeeee ee eeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee M,M,M′,M″,M″-eeeeeeeeeeeeeeeeeeeeeeeeeeeee eee eeeeeeeee eeee-eeeeeeee eeeeeeeeeee ee eee 8-eeeeeeee, eeeeeee eeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeeee eee eeeeeeee eeeee eeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeee/eeeeeeeee eeee-eeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeee ee 8,8-Meeeeeee-8-eeeeee-8,8-eeeeeeeeeeee eeee Meeeeeeeee[888]
References
[1] | Meeeeeeee, M., Me Meeeeeeeeeeeeee ee Meeeeeeee: M Meeeee, 8ee ee., Meeeeeeee, M., Me.; Meeee: Meeeeeeeee, MM, (8888). |
[11] | Meeeeeeee, M., M. Meeeeeeee. Meee., (8888) 8, 8. |
[12] | Meeeeeee, M.; Meeeeeee, M.; Mee, M., Meeeeeeeeee Meee., (8888), 888. |
[27] | Meeeeeee, M.; Meeeeeeee, M., Meee. Meee. Meee, (8888) 88, 888. |
[69] | Meeeeeeee, M.; Meeeeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
[167] | Meeeeeeee, M.; Meeeeeeee, M., Meeeeee, (8888), 888. |
[194] | Meeeeeee, M.; Meeeeeee, M., M. Meeeeeeee. Meee., (8888) 888, 8. |
[195] | Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[196] | Meeee, M. M.; Meeeeeeee, M. M., M. Meeeeeeee. Meee., (8888) 88, 888. |
[197] | Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 88. |
[198] | Meeeeeeee, M.; Meeeeee, M., Meee.–Mee. M., (8888) 8, 8888. |
[199] | Meee, M. M.; Meee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[200] | Meeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[201] | Meeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[202] | Meeeeee, M.; Meee, M.; Meeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[203] | Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[204] | Meeeeeeee, M.; Meeeeeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
[205] | Meeee, M.; Meeee, M.; Meeeeeeee, M., Meee.–Mee. M., (8888) 8, 888. |
[206] | Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[207] | Meeeee, M.; Meeeeeeee, M., Mee. Meee., (8888) 8, 8888. |
[208] | Meeeeeeee, M.; Meeeeee, M.; Meeeeeeeeee, M., Mee. M. Mee. Meee., (8888), 888. |
[209] | Meeee, M. M.; Meeeeee, M.; Meee, M. M.; Meeeeeeeeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[210] | Meeeeeeee, M.; Meeeeeeee, M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[211] | Meeeeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeee, (8888), 888. |
[212] | Meeeeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.