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Jonczyk, A.; Kowalkowska, A., Science of Synthesis, (2006) 8, 1142.
Aliphatic nitriles, including acetonitrile, can be deprotonated or alkylated by using sodium amide.[9–11] Nitriles possessing more than one acidic hydrogen are susceptible to polyalkylation,[9–12] particularly when the introduced group increases the acidity of the product.[13] Acetonitrile and other aliphatic nitriles can be exhaustively alkylated by treatment with an excess of sodium amide and an alkylating reagent.[9–11] Sodium amide can also be used in the alkylation of aliphatic N,N-dimethylcarboxamides or N-methylpyrrolidin-2-one.[14]
Mee eeeeeeee ee ee α-eeee eeeee ee e eeeeeee[8–88,88,88,88] ee ee eeeee[88] eeeeeeeeeee eeeeeeeeeee eeeeeeeee. Meeeee eeeee ee eee e eeeeeeee eeee eee eeeeeeeeee eeeeee eeeeee eeeeeeeeeeee,[88] eee eeeeeeeeeeee,[88–88] α-eeeeeeeeeeeeeeeee, eee eeeeeeeeeeeeee eeeeee[88] eee eeeeeeeee ee eeee eeeeee. Meee eeeeeeee ee eee eeeeeeeeee ee MM eeeee 8 ee eeee eeeeeeee 8 eee eeeee ee Meeeee 8.
Meeeee 8 Meeeeeeeee ee Meeeee, Meeeeeee, ee Meeeee[88,88,88–88]
M8 | M8 | MMM | M8M | Meeeeeeeee | Meeee (%) ee 8 | Mee |
---|---|---|---|---|---|---|
Me | Me | MM | MeMe | eeeeeee, eeeeee, 8.8 e | 88 | [88] |
Me | MMe8 | MM | MeMe | eee MM8, Me8M | 88 | [88] |
Me | M | MMMMe8 | MeMe | eee MM8, 8.8 e | 88 | [88] |
Me | M | MM8Me | Me8MMMe | eee MM8, Me8M, 8 e | 88 | [88] |
Me | M | MM8e-Me | MeM | eee MM8, Me8M, 8 e | 88 | [88] |
Me | Me | MM8Me | MeMe | eee MM8, Me8M, 8 e | 88 | [88] |
8-MeM8M8 | M | MM8Me | MeMe | eee MM8, Me8M, 8 e | 88 | [88] |
Me | M | MM8Me | Me(MM8)8Me | eee MM8, Me8M, 8 e | 88–88 | [88] |
Meeeee eeeee eee eeee ee eeee ee eeeee eee eee Meeeeee eeeeeeeeeeee ee eeeeee[88,88] ee eeeeee[88] ee α-eeeeeeeeeeeeee eeeee (eee eee eee eeeeeeeeeeeee eeeeeeee ee α-eeeeeeeeeeeeee[88]). Me eee eeee ee eeee ee Meeeeeeee[88,88] eee Meeeee–Meeeeee[88] eeeeeeeeeeeee; ee eeeeeeeee ee eeeeee eeee eeeeeeee[88,88] ee, eeeeeeeeeeee, eeeeee[88] ee eeeeeeeee ee eeeeeee; eee ee eee eeeeeeeee ee eeeeeeee,[88,88] eeee ee eee eeeeeeeee ee eeeee eeeeee 8 eeee eeeeeeee 8 (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee Meeeeeee[88]
Meeeeee eeeeeee eeee eeeeee eeeee eeeeee eeeeeee eeeeee eeee eee ee eeeeeeeee[8,88] ee eeeeeeee.[8,88–88] Meeeeeee ee eeeeeeeeeeeeee, M- eeeeee M-eeeeeeeeeeee, eee eeeeeeeeeeeeee (ee eee eeee ee eeeeeeeeeeeee eeeeeee) eeeeee eeeeee ee eeeee eeee eeeeeee.[8] α-(eeee-Meeeeeeeeeeee)eeeee eeeeee eeeeeee eeeeeee eeeeeeeeee eeee e eee eeeeeeeeeee eee eee eeeeeeee α ee eee eeeeee eeee.[88]
Mee eeeeee eeeeee ee 8- eee 8-eeeeeeeeeeeeeeeeee[88] eee 8- eee 8-eeeee eeeeee eeeeeeee[88] eee eeeeeeeeeeee eeeeeeeee ee eeeeee eeeeeeeeeeeee ee eeeeee eeeee ee, eee eeeeeee, ee eee eeeeeeeeee ee eeeeeee eeeeeeeeeee 8 eeee eee eeeeeeeee eeeeeeeeeee 8 (Meeeee 8).
Meeeee 8 Meeeeeee Meeeeeeeee ee Meeeeeeeeeeeeeeeeee eee Meeee Meeeee Meeeeeee[88,88]
Mee 8-eeeeee eeeee ee 8,8-eeeeeeeeeeeeeeee, 8,8,8-eeeeeeeeeeeeeeeee, ee 8,8-eeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeeee eeee eeeeee eeeee ee eeeeee eeeeeee,[88,88] eeeeeee ee ee eee 8-eeeeee eeeee eeee eeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee.[88] Mee eeeeeeeeee ee eeeee eeeeee eeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee ee 8,8-eeeeeeeeeeeeeee-eeeeeeeee eeeeee eeeee eeeee eeeeee 8-eeeeeeeeeeeeeee eeeeeeee ee eeee eeeeee.[88]
Meeeeeeeee eeeeee eeeeeeeeeeee, eeee ee eeeeeeeeeeeeeee,[8] eeeeeeeee eee eeeee eeeeeee,[88–88] eeeeeeeeeeee,[88] eee eeeeeeeeeeeeeee,[88] eeee eeeeee eeee eeeeee eeeee eeee eeeeeeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeee eeeeee ee eeeeee eeeeeee.[88] Meeeeeeee ee eee eeeeee eeee ee eeeeeee eeee eeeeeeee eeeeeeeee eeeee eee eeeeeeeeeeeee eeeeeeee;[88] ee eeee eeee, eee eeeeeee eeeeee eeee eee eeeeee eeeeeeeee eeeeeee eeeeeeeeeeeee eeee eee eeeeee.[88] Meeeeeee eeeeeeeee ee eeeeeeeeeeee eeee eeeeee eeeee eee eeeeeeeee ee eeeeeee eeee eee eeeeeeeeeeeee eeeeeeee ee 88–88% eeeee.[88]
Meeeeeee eeeeee eee eeee ee eeeeee ee eee eeeeeeee ee eeeeee eeeee (e.e., ee eee eeeeeeeeeee ee 8-eeeeee-8M-eeeeee eeee eeeeee eee eeeeeeeeeee[88] ee ee eeeeeeeeeeeeee eeee eeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeee).[88] Meeeee eeeee eeee eeeeeeee eee eeeeeeee ee eeee eeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeee, eeeeeeee eeeeeeeee–eeeeeeeee eee eeeeeeee–eeeeeeeeeee eeeeeeee eee eeee eeeeeeeeeee.[88]
Mee eeeeeeeee ee eeeeeeeeee eeeeeeeee ee eeeee eeeeeee eeeee eee eeeeeeeee ee Meeeeee 8.8.8.8.8.8.
Meeeeeeeeeee Meeeeeeee
Meeee 8,8-Meeeeeeeeeeeeeeee [8, M8 = Me; M8 = M; M8 = (MM8)8Me; MMM = MM8Me]:[88]
Meeeeeeee eeee (Meeeee; Meeeee; Meeeee, Meeeeee Meeeeeeee, Meeeeeeeee Meeeee M), Meeeeeeee (8888), e 888, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.
MMMMMMM: Meeeee eeeee eeeeeeeeee eeeeeee ee eeeeeeee ee eeeeeee ee eeeeeeee ee eee eee eee eeee ee e eeeeee eeeeeeee.
M eeee ee MeMM8MM8Me (8, M8 = Me; M8 = M; MMM = MM8Me; 88.8 e, 88.8 eM, 888 eeee) ee eeeee Me8M (88 eM) eee eeeee eeeeee 8 eee ee e eeeeeeeeee ee MeMM8[8] (888 eeee), eeeeeeee eeee Me (8.8 e, 888 eeee) ee eee MM8 (888 eM), eee eee eeeeeee eee eeeeeee eee 88 eee. M eeee ee Me(MM8)8Me (88.8 e, 888 eeee) ee eeeee Me8M (88 eM) eee eeeee eeeeee 8 eee, eee eeeeeee eee eeeeeee eee 8 e, eee eeee ee eee eeeeeeeeeee ee eeeeeeee ee MM8Me (8.88 e, 888 eeee). Mee Me8M (888 eM) eee eeeee, eee eee MM8 eee eeeeeeeeee ee eeeee e eeee eeeee eeee. Mee eeeeeee eee eeeeee ee 8°M eee eeeeeeeeee ee eeeeeeee eeeeeeee ee 8 M MMe (888 eM). Meeee eeeeeeee eee 88 eee, eee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeeeeeeeeeee eeee eee. ee MeMMM8 eee eeeee (8 × 88 eM), eee eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 88.8–88.8 e (88–88%); ee 888–888°M/8.8 Meee.
8-Mee-8-eeeeeeeeeeeeeeeeeeee (8, M8 = M; M8 = Me):[88]
MMMMMMM: Meeeee eeeee eeeeeeeeee eeeeeee ee eeeeeeee ee eeeeeee ee eeeeeeee ee eee eee eee eeee ee e eeeeee eeeeeeee.
M eeee ee MeMM (88.8 e, 888 eeee) ee ee eeeee eeeeee ee eeeee Me8M eee eeeee eeeeee 8 eee ee e eeeeeee eeeeeeeeee ee MeMM8 (888 eeee) ee eee MM8 (888 eM). Meeee 8 eee, e eeee ee MeMMe (88 e, 888 eeee) ee ee eeeee eeeeee ee Me8M eee eeeee ee eeeeeee ee eeeeeeee (eeeee 8 eee), eee eee eeeeeee eee eeeeeee eee 8 e. Me eee eeeeeee eeeeee eee eeeeeee, eeee Me8M eee eeeee ee eeeeeeeeee eeeeeeee. Mee MM8 eee eeeeeee eeeeeee (eeeee 88 eee) ee e eeeee eeee ee Me8M eee eeeee ee eeeeeeee eee eeeeee ee eeeeeeeeeeeee 888 eM. Mee eeeeeee eee eeee eeeeeeeeee eeeeee eeee eeeeeeee eeee eeeeeee eee (888 e), eee eeeeee eeee eeeeeeeee, eee eee eeee eeeeeee eeee eee eeeeeeee eeee eeeeeee eeeeeee Meeee Meeee Meeee-Mee ee eeeeee eeeeeee eeeeeeeee eeeeeeeee. Mee Meeee-Mee eee eeeeee eeee e eeeee eeeeee ee eee eeeee eee eee eeeeeeee eeeeeeee eeee eeeeeeeee eeee eee-eeee 8 M ee MMe. Mee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M (8 ×) eee eee eeeeeeee eeee eeeeee eeee ee MeMMM8 eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee, eee eee eeeeeee eee eeeeeeeeeeee (Me8M); eeeee: 88 e (88%); ee 88–88°M.
References
[3] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 88; eee e 888. |
[4] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
[6] | Meeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. M, (8888), 888. |
[9] | Meeee, M. M., Meeeee Meeeeeeee Meeeeeeee, Meeeeeee: Meeee Meee, MM, (8888), e 888. |
[10] | Meee, M. M.; Meeeee, M. M.; Meeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 888. |
[11] | Meeeeeeeeee, M.; Meeee, M. M.; Meee, M. M., Mee. Meeee. (M. M.), (8888) 88, 8. |
[12] | Meeee, M. M.; Meeeeeeeeee, M.; Meeeeee, M. M., Me.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[13] | Mąeeeee, M., Meeeeeeeeee, (8888) 88, 888. |
[14] | Meeeeee, M. M.; Mee, M. M., M. Mee. Meee., (8888) 88, 888. |
[15] | Meeeeee, M. M.; Meee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
[16] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[17] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[18] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[19] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. M, (8888), 888. |
[20] | Meeeee, M. M.; Meeeeeeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 888. |
[21] | Meeee, M. M. M.; MeeMeeee, M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
[22] | Mee'eeee, M. M.; Meeeeeeee, M. M., Meeeee. Meeeee Meeeee. Mee. Meeeee., (8888) 88, 8; Meee. Meeee., (8888) 88, 8888. |
[23] | Meeeeeee, M. M.; Meeeeeeeee, M. M., Mee. Meeee. (M. M.), (8888) 88, 8. |
[24] | Meeeeeee, M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[25] | Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M., Meeeeeeee, (8888), 888. |
[26] | Mee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
[27] | Meeeeeeeee, M. M.; Meeeeeeee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 88. |
[28] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 88. |
[29] | Meee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[30] | Meeeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
[31] | Meeeee, M.; Meee, M.; Meee, M.; Meeeee, M., Meeee. Meeeee., (8888) 8, 888. |
[32] | Meee, M. M.; Meeeeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[33] | Meeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[34] | Meeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 88. |
[35] | Meeeee, M.; Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[36] | Meeeeee, M.; Meee, M.; Meee, M., Meeee. Meeeee., (8888) 88, 888. |
[37] | Meeeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 8. |
[38] | Meeeee, M. Me.; Meeeeeeee, M. M., Meeeee. Meeeee Meeeee. Mee. Meeeee., (8888) 8, 8. |
[39] | Meeee, M. M.; Meeee, M., Mee. Meeee., Meee. Mee. M, (8888), 8888. |
[40] | Meeeeeee, M. M.; Meeeee, M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[41] | Meeeeeeeeee, M. M.; Meeee, M., Meee. Meee. Meee. Meee-Mee, (8888) 88, 8888. |
[42] | Meeeeee, M. M.; Meeeee, M. M.; Meeee'eee'e, Me. M.; Meeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 888; Meee. Meeee., (8888) 88, 888888. |
[43] | Meeeeee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
[44] | Meeeeeee, M. M.; Meeeeeee, M. M.; Mee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[45] | Meeee, M. M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. M, (8888), 888. |
[46] | Meeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[47] | Meeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 888.