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Please login to access the full content or check if you have access via8.2.11.1.1 Variation 1: Monometalation of Alkylarenes
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Mordini, A.; Valacchi, M., Science of Synthesis, (2006) 8, 1227.
Toluene is instantaneously metalated by pentylsodium[3] or other organosodium reagents[3–7] at the benzylic position, although some contamination by the ring-metalated product has been observed.[8] Phenylsodium also undergoes reaction with toluene to give benzylsodium (1) (Scheme 1),[9] but under reflux and with longer reaction times, whereas the reactions with diphenyl- and triphenylmethane occur even at room temperature.[10] Predominant α-metalation is observed when ethylbenzene is treated with pentylsodium, but only in low yields and with poor selectivity.[11,12] The addition of N,N,N′,N′-tetramethylethylenediamine greatly enhances the metalating power of pentylsodium just as it does with organolithium compounds. This reagent combination performs efficient monometalation of ethylbenzene (95% yield)[13] and cumene (up to 98% yield).[14]
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References
| [3] | Meeeee, M. M.; Meeeeeeeeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [4] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [5] | Meeee, M. M.; Meeeeeeee, M. M., Mee. Mee. Meee., (8888) 88, 888. |
| [6] | Meeeeeee, M.; Meeeeeee, M. M.; Meee, M.; Meeee, M., M. Meeeeeeee. Meee., (8888) 888, 888. |
| [7] | Meeee-Meeee, M.; Meeeeee, M. M., M. Meee. Mee., (8888), 8888. |
| [8] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [9] | Meeeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [10] | M'Meeee, M. M.; Meeeeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
| [11] | Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [12] | Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [13] | Meeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [14] | Meeeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [15] | Meeeeeeee, M. M.; Meeeee, M.; Meeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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