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Schall, A.; Reiser, O., Science of Synthesis, (2007) 25, 608.
The only sufficiently stable acid halide of formic acid is the fluoride, which was prepared in 1934 from anhydrous formic acid, potassium fluoride, and benzoyl chloride, albeit in a low yield of 16%.[10] The protocol was later improved by directly reacting benzoyl fluoride with formic acid.[11] Further improvements were disclosed, allowing the preparation of formyl fluoride on a large scale either from formic acid (employing potassium hydrogen fluoride as the fluorinating agent),[12] from acetic formic anhydride,[12] or from cyanuric fluoride.[13]
Meee eeeeeee eeeeeee eee eee eeeeeeeeeee ee eeeeee eeeeeeee (8) eeeeeeeee, ee eee eeeeeeeeeeee eeee ee eeeeeeeeeee eeee eeeee Meeee eeeee, eeeeeeeeee eeeee eeeeeeeeeee, eeeeeeeeeee eeee eeee eeeeeeeeeee eeeeee eeee ee eeeeeee eeeeeee eeeeeeee, e.e. ee eeee eee eeeeeeeeeee eeeeeeee 8 (Meeeee 8).[88]
Meeeee 8 Meeeeeeeeee ee Meeeeeee Meeeeeeee Meeee Meeeee Meeeeeee (Meee Meeeeeeeeee)[88]
Me8 | Meeee (%) | Mee |
---|---|---|
Me | 88 | [88] |
8-Mee | 88 | [88] |
Me8M8M8e | 88 | [88] |
Mee | 88 | [88] |
8,8,8,8-Me8M8M | 88 | [88] |
8-eeeeeeee | 88e | [88] |
e Meeeeee ee eeeeeee.
e Meeeeeee eeeeeeee eee eeeeeeeeeee; 88% ee 8-eeeeeeeeeeeee eee eeee eeeeee.
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee eeee eeeeee eeee: Me eeeee MMM8M (88 e, 8 eee) eee eeeee eee MMM8 (88 e, 8.88 eee). Me eeeeeee ee eee eeeeeee ee eee eeeeeeeee eee eeeeeeee. MeMe (888 e, 8 eee) eee eeeee ee eee eeeeeee eeeeeee, eeeee eee eeee eeeeee eeeeee ee e eeeee eeee. Meeeee eee eeeeeee MMMM eeeeeeeee. Meee MeMe, eeeee ee-eeeeeeeee, eee eeeeeeeee ee e eeeeeeeee eeeeee eeee ee eee/eeee eeeeeee. Mee eeeeeee MMMM eeeeeeeee ee e eee eee/eeeeeee eeeeee eeee. Mee eeeee eeeeeee eee eeeeeeeeeee ee e eee-eeeeeeeeeee eeeeee ee eeee eee eeee eeeeeee; eeeee: 88 e (88%); ee −88°M; MM (eee) ν̃eee: 8888 eee 8888 (M—M); 8888, 8888, eee 8888 (M=M), 8888, 8888, eee 8888 ee−8 (M—M).
MMMMMMM: Meeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeee.
Meeeeeeeeee eeee eeeeee eeeeee eeeeeeeee: Meeeeeee eee eee eeeeeeee ee eeeeeeeeeee eeeeeeee, MeMMMM (88 e, 8.8 eee) (eeeeeeee eeee eeeee MMM8M eee eeeeee) eee eeeeee ee e eeeee eeeeee eeeee eeeeeeeee ee e eeeeeeeeee eeeeeeeee eeee e eee eee eeeeee eeee. Meeee MM (88 e, 8.8 eee) eee eeeee ee −88°M eee eee eeeeeeeeeee ee eee eeeeeee eee eeee eeeeeee ee eeee eeeeee ee 8°M. Mee eeeeeee eee eeee eeee ee eeee eeeeeeeeeee eee 8 e. MMMM eeeeeeeee eeee eeeeeeeeeeee ee ee eee eeeeee eee eee eeeeeeeee ee eee eee eee eeeeee eeee. Mee eeeee eeeeeee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee ee e eee-eeeeeeeeeee eeeeee (ee −88°M), ee eeee eee eeeeeee eeee eeee e eeeee eeeeee ee MeM eeeeeeee; eeeee: 88 e (88%).
Meeeeeee Meeeeeeee 8; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeee eeeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee.
Mee eeeeeee eeeeeeee eeeeeeeeeee (8.8 eee) eee eeeeeeeee ee MM8 (888 eM). Mee eeeeeeeeeee ee eee eeee eee eeeeeeeeee ee 8–88°M eee e eeee eeeeee ee e eeeeeee ee MMMM eee MM8 (8:8) eee eeeeee eeeeeee eee eeee eeee eeeeeeee. Meeee 8 e, e eeeeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee ee 8.8 eee ee MMMM eee eeeeeeee (ee eee eeee ee eee eeeee–eeeeeeee eeeeeee) eee eee eeeeeeeeeeee ee eee eeeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeee eee eeeeeee 8.8 e, eeeeee eeee eeee M8M ee eeeeee eee eeee, eeeee (MeMe8), eee eeeeeeeeeeee.
References
[10] | Meeeeeeeee, M. M.; Meee, M. M., Mee. Meeee. Meee. Mee. M, (8888) 88, 888. |
[11] | Meeeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 88, 888. |
[12] | Meee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[13] | Meee, M. M.; Meeeee, M.; Meeeeee, M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 88.