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Please login to access the full content or check if you have access via41.1.1.5.66 Method 66: Addition to a Nitroalkene Using a Carbanion Prepared from a Nitroalkane
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Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 206.
Addition of nitroalkyl anions to nitroalkenes gives 1,3-dinitroalkanes as products. Examples are shown in Scheme 285.[745–750] This reaction has also been performed efficiently using thiourea organocatalysis.[751]
Meeeee 888 Meeeeeee ee Meeeeeeeee Meeeee ee Meeeeeeeeeee[888–888]
| M8 | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | Me | M | Me8M (eee.), eeee, ee, 88 e | 88 | [888,888] |
| Me | Me | M | Me8M (eee.), eeee, ee, 8 e | 88e,e | [888,888] |
| Me | Me | Me | Me8M (eee.), eeee, ee, 88 e | 88e | [888,888] |
| M | eeeee-8-ee | M | MeMM8 (eeeeee), Meeeee M, MMM/MeMM, ee, 88–88 eee | 88 | [888] |
| M | 8-Me8MM8M8 | M | MeMMM8, MeMM8, eeeeee, 8.8 e | 88 | [888] |
| M | 8-Me8MM8M8 | M | MM, MeMM8, eeeeee, 8.8 e | 88 | [888] |
| M | Me | M | MeMM8 (eeeeee), Meeeee M, MMM/MeMM, 8°M, 8 e, eeee ee, 8 e | 88 | [888] |
e Meeeeee ee eeee eeeeeeeeeeeee.
e Meeeeee eee eeeeeeeee eeee eee eeeee ee eeeeeeeeeee ee 88 eee 88% eeeeee.
Meeeeeeeeeee Meeeeeeee
8-(8,8-Meeeeeeeeeeee-8-ee)-8-eeeee-8-eeeeeee-8-(8-eeeeeeeeeeeee)-8M-eeeeee (888); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeee ee eeeeeeeee, e eeeee- eee eeee-eeeeeeeee eeeeeeeee, eee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee.
Me e eeee ee eeeeeeeeeee 888 (8.88 e, 88 eeee) ee MMM (88 eM) eeeee M8 eee eeeee MeMM8 (88 eM), eeeeeeee ee e 88% eeee ee Meeeee M ee MeMM (88 eM, 88 eeee) eee eee eeeeeee eee eeeeeee eeeeeeeeee ee ee eee 8 e. Meeeeeeee eeeeeeeeee ee eee eeee eee eeeeeeee. Mee eeeeeee eee eeee eeeeee eeee 8 M MMe (8×88 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (88 eM) eee eee eeeeeee eee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee); eeeee: 8.88 e (88%); ee 888–888°M; 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M), 8.88 eee 8.88 (MM′MM′ eeeeee, 8M, M = 8 Me), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M), 8.88 (e, 8M), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me).
References
| [745] | Meeeeee Meeeeeeee, M.; Meeee Meeáeeeee, M. M.; Móeee-Máeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [746] | Meeee Meeáeeeee, M.-M.; Meeeeee Meeeeeeee, M.; Móeee-Máeeeee, M.; Meáeee, M. M.; Meeeeee, M. M.; Móeee-Meeeee, M.; Méeee-Meeeeee, M., Meeeeeeee, (8888), 88. |
| [747] | Meeeeeee, M.; Meeeeee, M.; Meeeee, M., Meee. Meeee. (Meeeeeee, Mee.), (8888) 888, 888. |
| [748] | Meeeee, M.; Meeeeee, M. M.; Meeúeeeee-Meee, M.; Meeee-Meeeee, M.; Meeeeee, M. M., M. Meee. Mee., Meeee., (8888), 888. |
| [749] | Meeeeeee, M.; Meeeeee, M., Meee. Meeee. (Meeeeeee, Mee.), (8888) 888, 888. |
| [750] | Meeeeeee, M.; Meeeeee, M.; eee Meeeeee, M., Meee. Meeee. (Meeeeeee, Mee.), (8888) 888, 888. |
| [751] | Meeeeeeee, M.; Meeee, M. M., Meeeeee, (8888), 8888. |
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