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Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 119.
When nitroalkyl anions are treated with bromoalkanes, the O-alkylation side reaction occurs more easily than with chloroalkanes (see Scheme 154, Section 41.1.1.5.1.2). Despite this, many successful alkylations using salts of nitroalkanes have been achieved by modifying the base and solvent used, as well as by using different additives. Examples of simple nitroalkane alkylations with bromoalkanes are shown in Scheme 158.
Meeeee 888 Meeeeeeee ee Meeeeeeeee Meeeee eeee Meeeeeeeeeee[888,888–888]
| M8 | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| MM | Me | MMMe8 | Me eeee ee eeeeeeeeeee, eeeeeee, ee, 8 e | 88–88 | [888] |
| M | MM8Me | MM8MM8Me | MeMMe, MMM/MeMM, ee, eeeeeeeee | 88 | [888,888] |
| M | MM8Me | (MM8)8MM8Me | Me eeee ee eeeeeeeeeee, 88°M, 8 e | 88.8 | [888] |
| Me | Me | (MM8)8MM8Me | MeMMe, MMM, ee, eeeeeeeee | 88 | [888] |
| M | MM8Me | Me | MeMMe, MMMM, ee, 88 e | 88 | [888] |
| M | MM8Me | Me | MMMM8, MMM, 88°M, 88 e | 88 | [888] |
| Me | MM8Me | Me | MMMM8, MMM, 88°M, 88 e | 88 | [888] |
| Me | Me | MM(MM8Me)MMMe | MeMe, MMM, −88°M, 8 e | 88 | [888] |
| Me | Me | MM(MM8Me)MMMe | MeMe, MMM, −88°M, 8 e | 88 | [888] |
| (MM8)8 | MMe8MM | e-MeMM, MMMM, ee, 8 e | 88 | [888] | |
| M | MM8Me | MM8MM=MM8 | MMMM8, MMMM, eeee, ee, 88 e | 88 | [888] |
| M | MM8Me | 8-MMM8M8MM8 | eMe8MMe, MMMM, MMM, 8–88°M, 8 e | 88 | [888] |
| M | Me | (MM8)8Me | MeMe, MMM/MMMM, −88°M, 88 e | 88 | [888] |
Mee ee eeee eeeeeeee ee eee eeeeeeeee ee eeee eeeeeee eeeeeeeeee ee eeeee ee Meeeee 888. Mee eeeeeeeee eeeeeee e eeeeeeeeeee[888] eee eee eeeeeeee ee e eeeeeeeeeee eeee eeeeeee eeeeeee 888[888] (eee eeeeeeeeee eeeeeeeeeee eee Meeeeee 88.8.8.8.88).
Meeeee 888 Meeeeeeeee ee Meeeeeeeeeee eeee Meeeeeeeeeee[888–888]
Meeeeee eeeeeeeeee eee eeeee ee Meeeee 888. Meeee eeeeeee ee eeeeeeeeeeeeeee eeeeeeee,[888] e eeeeeee-eeeeeeeee eeeeeeeee,[888] eee eee ee e eeeeee eeeeeeee ee eeeeeeee M-eeeeeeeeee ee eeeeeee ee M-eeeeeeeeee.[888]
Meeeee 888 Meeeeee Meeeeeeeee ee eee Meeeeeeeee ee Meeeeeeeeeee eeee Meeeeeeeeeee[888–888]
Meeeeeeeeeee Meeeeeeee
Meeeee (M)-8-(eeee-Meeeeeeeeeeeeeeeeee)-8-[8-(eeeeeeeeeeeeeee)-8-eeeeeeeee-8-eeee]-8-eeeeeeeeeeeeeeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
Me e eeeeeeeeee ee MeM (88 ee, 8.88 eeee) ee MMM/MMM (8:8; 88 eM) ee 8°M eee eeeeee eeeee eeeeee eeeeeeeeeeee (8.888 e, 8.88 eeee). Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeee ee 8°M. Meeeeeee 888 (8.88 e, 8.88 eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee eee 88 e. Me eee eeee eeeeeee eeee eee. ee MM8Me eee eeeeeeeee eeee MeMMe (8×88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee 8:8) ee eeee 888 ee e eeeee eeeeee eee; eeeee: 8.888 e (88%).
References
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| [471] | Meee-Meeee, M.; ee ee Mee, M.; Meeeee, M., Meeee. Meeeee., (8888) 88, 8888. |
| [472] | Me, M.; Meeeeeeeeöe, M. M. M.; Meeeee, M. M.; Meeeeeee, M. M.; MeMeeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
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| [475] | Meeeeee, M.; Meeeeeeeee, M.; Meeeeee, M.-M., Meeeeeeee, (8888), 8888. |
| [476] | Meeeeeeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
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