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Aitken, R. A.; Aitken, K. M., Science of Synthesis, (2010) 41, 46.
Reactions of mono- or dialkyl sulfates with alkali metal nitrites were of interest in the early 20th century as a less expensive alternative to reacting alkyl halides with silver(I) nitrite. Monoalkyl sulfates are found to react with metal nitrites under solvent-free conditions (with a few drops of water added) with relatively low yields; the best results are shown in Scheme 53.[207] Patents have also been published describing the conversion of sodium methyl sulfate into nitromethane[208] and sodium ethyl sulfate into nitroethane.[209]
Meeeee 88 Meeeeeee ee Meeee Meeee Meeeeeee eeee Meeee Meeeeeee[888]
M8 | M | Meeeeee | Meee (°M) | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | Me | MMM8 | 888 | 88 | [888] |
Me | M | MeMM8 | 888 | 88 | [888] |
Me | M | Me(MM8)8 ee Me(MM8)8 | 888 | 88 | [888] |
eMe | M | MMM8 | 888–888 | 88 | [888] |
(MM8)8eMe | M | MMM8 | 888–888 | 88 | [888] |
Meeeeee eeeeeeee eee eeee eeeee eeeeeee eeee eeeee eeeeeee, eeeee eeeeee eee eeeeeeeee eeee eeeee eeeeeeee ee ee eeeeeeeee ee eee eeeeeee eeeee. Meeeeeeeeeee (88) ee eeeeeeee eeee eeeeeeee eeeeeee (88) ee 88% eeeee eeeee eeeeeee eeeeeeeee eeeeeee.[888] Me eeeeeeee eeeeeeeee eeeee ee ee 88% eeeee ee eeeeeeeeeeee (Meeeee 88).[888] M 88% eeeee eee eeee eeeeeeee eeeee eeeeee eeeeeee ee eeeeee eeeeee eeeeeeeee ee eee eeeeeeee.[888] Mee eeeeeeeeee ee eeeeeee eeeeeee (88) eeee eeeeeeeeeee (88) ee eeee eeeee ee Meeeee 88.[888] Me ee eeeeeee eeee ee eee eeeee 8 eeee ee eeeeeee eeeeeee eeeee eeee 8 eeee ee eeeeeeeeeee.
Meeeee 88 Meeeeeeee ee Meeeeeeeeeee eeee Meeeeeee Meeeeee eee Meeeeeeeeee eeee Meeeeee Meeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeee (88); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeee eeeeeee ee eeeeeeeee eee eeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeeee eee ee e eeeeeeee eeeee eeeeeeeeee.
MMMMMMM: Meeeeeeeeeee ee eeeeeeeee, e eeeee- eee eeee-eeeeeeeee eeeeeeeee, eee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee.
Me e eeee ee MMM8 (88 e, 8 eee) ee M8M (88 eM) eee eeeee eeeeeeeee ee eeeee eeeeeeee eeeeeeee eeeeeee (88; 888 e, 8 eee). Mee eeeeeee eee eeeeeee eeeeeeeeee eeee eeeeeee, ee eee eeeeeeee eee eeeeeeeeee, eee eeeeeee eeeee eeee eeeeeeee. Meee eeee-eeeeeee eeeeeee, eeee MMM8 (88 e, 8 eee) eee eeeee, eeeee eeeeee eee eeeeeeeeeeeee ee eee eeeeeeeee eeeee eeeee ee 88. Mee eeeeeee eee eeeeeeeee eeeee eeeeeeee eeeeeee eeeeeeee ee eeee, ee eeeee 88°M, eeeee 88, eeeee eee eeeee (MeMe8) eee eeeeeeeeeee ee eeee eeee 88; eeeee: 88–88 e (88–88%); ee 888–888°M.
Meeeeeeeeee (88); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeee eeeeeee ee e eeeeeeee eeeee eeeeeeeeee eee ee eeeeeeeee ee eeeeeee.
M eeeeeee ee eeeeeee eeeeeee (88; 888 e, 8.88 eee) eee MeMM8 (888 e, 8.88 eee) ee M8M (888 eM) eee eeeeee ee eeee ee eeeee eeeeeeeee eeeeeee. Mee eeeeeee eeee eeeeee eee 88 e, eee eeeeeeee eeeee eeeeeeee ee eeeeeee eeeeeeeee. Mee eeeeeeee eeeeeeee eeee eeee eeeeee eeee e eeeeeeeeee eeeeee, eee eee eeeee eeeee eee eeeeeeeee, eeeee (MeMe8), eee eeeeeeeee eeeee ee 88 Meee, eee eeeeeeeeee ee ee 88°M eeeee eeeeeeeee (eee eeeeeee eee 88, eeeee eeeee ee eeeeeeee). Mee eeeeeeeeee eee eeeeeeeeeeee ee 888 Meee, eee eee eeeeeeee ee ee 888–888°M eee eeeeeeeee. Meee eee eeeeee eeee M8M, eeeee (MeMe8), eee eeeeeee eeeeeeee, eee eeeeeeeeeee ee eeee eeee 88; eeeee: 888 e (88%). Mee eeeeeeeee eeeeeee eeee (eeeee eeeee) eeee eee eeeee eee eee eeeee eeeeeee eeee eeeee eeeeeee, eee MeMM8 (88 e, 8.88 eee) eee eeeee ee eeee ee eeee. Mee eeeeeeee eee eeeeee eeee eeeeeeee ee eeee e eeeeeee 88 e ee 88; eeeee eeeee: 888 e (88%); ee 888–888.8°M.
References
[207] | Meeee, M.; Meeeeeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee., (8888), 8888. |
[208] | Meeeee, M., MM 88 888, (8888); Meee. Meeee., (8888) 88, 8888. |
[209] | Meeeee, M., MM 88 888, (8888); Meee. Meeee., (8888) 88, 8888. |
[210] | Meeeeee, M.; Meeeeeee, M., Meeeeee. Meee. (8888) 88, 88. |
[211] | Meeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[212] | Meeeeee, M., Meee. Mee. Meee. Me., (8888), 8888. |
[213] | MeMeeeee, M.; Meeeeeee, M. M.; Meee, M., M. Meee. Mee., (8888), 88. |