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Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 47.
In the study mentioned in Section 41.1.1.1.27 where iodomethane was reacted with an ammonium nitrite, methyl methanesulfonate and methyl trifluoromethanesulfonate were also reacted with nitrites, and the product mixtures are similarly analyzed by NMR (reactions run in CDCl3) or gas chromatography. The results are shown in Table 8. The highest selectivity in favor of the nitroalkane product was obtained using potassium nitrite/18-crown-6 in ethanol.[206]
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M8 | Meeeeeeeee | Meeeeee | Meeeeee Meeee (MeMM8/MeMMM) | Mee |
---|---|---|---|---|
Me | MMM8, 88-eeeee-8, ee | MeMM | 88:88 | [888] |
MeMM | 88:88 | [888] | ||
MMM | 8:88 | [888] | ||
eeeeeee | 88:88 | [888] | ||
Me | Me8MMM8, ee | MMMe8 | 88:88 | [888] |
MM8 | Me8MMM8, ee | MMMe8 | 88:88 | [888] |
Mee eeeeeeee ee eeeee eeeeeeeeeeeeeeeee eeee eeeee eeeeeeee eee eeee eeeeeeee ee eeee eee eeeeee eee eee eee eeee eeee eeeeee ee eee eeeeeeeee ee eeeeeeeeeeee. Meeeeeeeeeee ee eeeeeeee ee eeeeeee eeeeee 8-eeeeeeeeeeeeeeee eee eeeeee eeeeeee.[888] Me e eeeee eeeeee, eeeeee, eeeee, eee eeeee 8-eeeeeeeeeeeeeeeee eeee eeeeee ee eeeee eeee eeeeee eeeeeee eee 8 eeeee ee eeee, eeeee eeeee eeeeeeeeeeee, eee eeeeeeeeeeeee eeeeeeeeeeee ee 88, 88, eee 88% eeeeee, eeeeeeeeeeee.[888]
References
[206] | Meeeeee, M. M.; Meeeeeeeeeee, M.; Meee, M.; Meeeee, M.; Meee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[214] | Meeeeeeee, M., Meee. Mee. Meee. Me., (8888) 88, 888. |
[215] | Meeeeeeee, M.; Meeeeee, M., Meeeeee. Meee., (8888) 88, 888. |