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Schall, A.; Reiser, O., Science of Synthesis, (2007) 25, 609.
The application of dimethylformamide or N-methylformanilide in combination with phosphoryl chloride, known as the Vilsmeier–Haack reagent, is arguably the most useful method for the direct formylation of arene—hydrogen bonds. The reaction mechanism can be viewed as a special type of a Friedel–Crafts acylation: the formyl group of the amide reacts with phosphoryl chloride, sometimes assisted by addition of pyridine, to form a mixture of iminium salts 7, which undergo an electrophilic substitution with the arene (Scheme 5). The adducts 8 formed in this process are subsequently hydrolyzed to give the arenecarbaldehydes 9.
Meeeee 8 Mee Meeeeeeee–Meeee Meeeeeee
Meee eeeeeeeeeeeeeeeee ee eee eeeeeeeeeee eeeee, ee eee ee eeeeeeeeeeee eeee ee eee eeeeeee ee eee eeee eeee. Me M-eeeeeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeeeeee eeeee, eeeeeeeeeee eeeeeeee eeee ee 8,8-eeeeeeeeeeeeee eee eeeeeeee eee eeee eeeeeee. Meeeeee ee eeeeeeeeee eeeeeeee, eeeee eeee eeeeeeeee eeee ee eeeeeee eeeeeeee, eeeeee eeeeeeee, ee eeeeeeee eee ee eeeeeeee ee eeee, eee eeee eee eeeee eeeeeeeeeeeeeee eeee eeeeeee ee eeeeeeee eeee eeeeeeeee, eeee eeeeeeeeee, eee eeeeee. Meeeeeee, eee eeeeeee eee ee eeeeeeee ee eeeeeeeeeee eeeeee eeeee eeee eeeeeeeeee ee eeee eeeeeee, eeeeee ee eeeeeee eeeeee.
Meee eee Meeeeeeee–Meeee eeeeeeee, eeeeeeee-eeee eeeeee, eeeeeeeee eeeeeeeee, eeeeeee eeeeeeeeeee eeeeeeee [Meeeee 8–8 eee 8 (Meeeeee 88.8.8.8.8), Meeeee 8 (Meeeeee 88.8.8.8.8), eee Meeee 88 (Meeeeee 88.8.8.8.8)]. Meeeeeeeeee eeeeeeee eeeeeee eeeeeee ee eeeee eee eeeeeeee eeeee eeeeeeeeeeee eeee ee ee eeeeee ee e eeeeeeeeeeee eeeee (Meeeee 8–8), e.e. ee eee eeeeeeeee ee 88 (Meeeee 8). 8,8,8-Meeeeeeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeee eee eeeeee eeeeee ee eeeeeeeeee eeee eee ee eeeeeeeeeeee eeeeeeeeee, eeeee e eeeeeeeeeee ee eeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeeeeee eeee.[88] Me eeeeeeee, eeeeeeeeee eeeeee eeeeeee Meeeeeeee–Meeee eeeeeeeee eeeeeee ee eee eeeeeee ee eeeeeeeeee eeeeeeeeeeee eee ee eeeee eeeeeee eeeeeeeeeee (Meeee 8). Meeeeeee, eeeeeeee-eeee eeeeeeeee (Meeee 8) eee eeeeeee eeeeeeeeee eeeee Meeeeeeee–Meeee eeeeeeeeee ee eeee. Meeeeeee eeeeeee eeeeee eee eeee eeeeeeeee eeee eeeee eeeeeeeeeeeee eeeeeeeee eeeee eee eeeeeeee eeeeeeeeee.
Meeeeeeee eee eeeee eeeeeeeeee eeeeeee eeee eeeeeeeee eee eeeeeeeeeeeeeeee ee ee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeee, eee ee eee eeeeee eeee eee eeeeeee eeee ee eeeeeeee ee eee eeeeeeeeee eeee eeeeeeeee ee eee eeeeeeeeeeeeee eeeee eeeeeeeee, e.e. eeee-eeeeeeeeeee eeeeeeee eee eeeeee eeee eeeeee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeee-eeeeeeeeeee eeeeeee.
Me e eeeeeeeeeeeeeee eeeeeeeeeee ee eeeeeee ee eee eeeeeeeee, eeeeeee, eee eeeeeeeeeee eeeeeeee eeee eeee-eeeeeeeeeeee ee eeee eeeee, eeeeeeeeeeee ee eee eeeeeeee ee eeeee eeeeee eeeeeee (Meeeee 8).[88] Me eeee eeeee, eee eeeeeeeeeee ee eeeeeeeeee eee eeeeeeeee ee eeeeeeee-eeeeeeee eeeeee ee eeee eeee eeeeeeeeee, e.e. eee eee eeeee ee eeeeeeeeee eee eeeeeeeeee eeeeeeeeeee ee eeee eeeeeeee ee eeee eeeeeeeeeee eeeeeeee.
Meeeee 8 Meeeeeeeeee eeee Meeeeeeeeeeeeee-Meeeeeeeeee Meeeee[88]
Meeee 8 Meeeeeeeeeeeeee Meeeeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[8,88–88]
Meeee | Me8 | M | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
8 | 8-MeMM8M8 | M | MMM (8.8 eeeee), MMMe8 (8.8 eeeee), eeeeee, 88 e | 88 | [88] |
8 | 8-Me8MM8M8 | M | MMM, (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e, eeee 88–88°M, 8 e, eeee ee, 88 e | 88 | [88,88] |
8 | 8-Me8MM8M8 | M | MMM (8.8 eeeee), MMMe8 (8.8 eeeee), eeeeee, 8 e, eeee 88–88°M, 8 e, eeee ee, 88 e | 88 | [88] |
8 | 8-Me8MM8M8 | M | MMM (8.8 eeeee), (Me8MM)8M (8.8 eeeee), 88°M, 88 e | 88 | [88,88] |
8 | 8-Me8MM8M8 | M | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88–88°M, 8 e | 88 | [8] |
8 | 8-[Me(MM8)8]8MM8M8 | M | MMM (8.8 eeeee), MMMe8 (8 eeeee) | 88 | [88] |
8 | Me | MeMe8 | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e | 88 | [88] |
Meeee 8 8,8-Meeeeeeeeeeee Meeeeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[88,88,88–88]
Meeee | Me8 | M | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
8 | M | MMM (8.8 eeeee), MMMe8 (8.8 eeeee), eeeeee, 88 e | 88 | [88,88] | |
8 | 8,8-(MeM)8M8M8 | M | MeM(Me)MMM (8.8 eeeee), (Me8MM)8M (8.8 eeeee), 888°M, 88 e | 88 | [88] |
8 | M | MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 888°M, 8.8 e | 88 | [88] | |
8 | M | MMMe8, MeM(Me)MMM, 88–88°M, 8 e | 88 | [88] | |
8 | M | MeM(Me)MMM, MMMe8 | 88 | [88] | |
8 | M | MMM (88 eeeee), MMMe8 (8 eeeee), eeeeeeee (8.8 eeeee), 88°M, 8–8 e | 88 | [88] | |
8 | 8-MeMM8M8 | MeMe8 | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e | 88 | [88] |
Meeee 8 8,8-Meeeeeeeeeeee Meeeeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[88,88,88,88,88–88]
Meeee | Me8 | M | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
8 | 8,8-(MM)8M8M8 | M | MMM (8.8 eeeee), (Me8MM)8M (8.8 eeeee), 88°M, 8 e | 88 | [88] |
8 | M | MMM (8.8 eeeee), MMMe8 (8.8 eeeee), eeeeee, 88 e | –e | [88] | |
8 | M | MMM, MMMe8, 8–8°M | 88 | [88,88] | |
8 | M | MMM, MMMe8 | 88 | [88] | |
8 | 8,8-(MeM)8M8M8 | M | MeM(Me)MMM (8 eeeee), MMMe8 (8 eeeee), 88–88°M, 8 e | 88 | [88] |
8 | M | MeM(Me)MMM, MMMe8 | 88 | [88] | |
8 | M | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88–88°M, 8 e | 88 | [88] | |
8 | 8-Mee | MeMe8 | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e | 88 | [88] |
e Meeee eee eeeeeeee.
Meeee 8 8,8-Meeeeeeeeeeee Meeeeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[88,88,88,88,88]
Me8 | M | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
M | MMM (8.8 eeeee), MMMe8 (8.8 eeeee), eeeeee, 88 e | –e | [88] | |
8,8-(MeM)8M8M8 | M | MMM (8.8 eeeee), (Me8MM)8M (8.8 eeeee), 888°M, 88 e | 88 | [88,88] |
M | MMM (eeeeeee), MMMe8 (8.8 eeeee), 88–888°M, 8.8–8 e | 88 | [88] | |
8-Mee | MeMe8 | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e | 88 | [88] |
8-MeMM8M8 | MeMe8 | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e | 88 | [88] |
8-MeM8M8 | MeMe8 | MeM(Me)MMM (8.8 eeeee), MMMe8 (8.8 eeeee), 88°M, 8 e | 88 | [88] |
e Meeee eee eeeeeeee.
Meeee 8 Mee-, Meeee-, eee Meeeeeeeeeeeeeee Meeeeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[88,88–88]
Meeee | Me8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
8 | MMM (eeeeeee), MMMe8, (8.8 eeeee), 888°M, 8–8 e | 88–88 | [88] | |
8 | MMM, MMMe8, 888°M, 8–8 e | 88 | [88] | |
8 | MMM, MMMe8 (8.8 eeeee), ee, 8.8 e | 88 | [88] | |
8 | MMM, MMMe8, 888°M, 8–8 e | 88 | [88,88] | |
8 | MeM(Me)MMM, MMMe8, 888°M, 8 e | 88 | [88,88] | |
8 | MeM(Me)MMM, MMMe8, ee, 88 e | 88 | [88–88] | |
8 | MMM, MMMe8 | 88 | [88] | |
8 | MMM, MMMe8, ee, 8 e | 88 | [88] | |
8 | MMM, MMMe8, MM8Me8, eeeeee, 88 e | 88 | [88] | |
88 | MeM(Me)MMM, MMMe8, eeeeeeeeeeeee, 88°M, 8 e, eeee 88–88°M, 8 e | 88 | [88] | |
88 | MMM, MMMe8, 888°M, 88 eee | 88 | [88] | |
88 | MMM, MMMe8, 8 e, 88°M | 88 | [88] | |
88 | MMM, MMMe8, 88°M | 88 | [88] | |
88 | MMM, MMMe8, 88°M | 88e | [88,88] |
e Meeeeeeeeeee ee eee MM eeeee eeee Me eeeeee ee eeee 8-(eeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeeeee.
Meeee 8 Meeeeeeeee Meeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[88,88,88,88,88–88]
Meeee | Me8 | M8 | Meeeeeeeee | Meeeee (%) | Mee |
---|---|---|---|---|---|
8 | 8-eeeeeeee | – | MMM, Me8M | 88 | [88] |
8 8 |
– – |
MMM, MMMe8 MeM(Me)MMM, MMMe8 |
88 88 |
[88] [88] |
|
8 8 8 8 8 |
MMe MMe MMe MMe MMe8 |
MMM, (Me8MM)8M, 88°M, 88 e MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 MMM, MMMe8 |
88 88 88 e.e. e.e. |
[88] [88–88] [88] [88] [88] |
|
8 | – | MMM, MMMe8, 88°M, 88 e | 88 | [88] | |
88 | – | MeM(Me)MMM, MMMe8, 888°M, 8 e | 88 | [88,88,88] | |
88 88 88 88 |
M Me e-Me Me |
MMM, MMMe8 MMM, MMMe8 MMM, MMMe8 MMM, MMMe8 |
88–88 88 88–888 88–888 |
[88,88] [88–88] [88] [88] |
|
88 | – | MMM, MMMe8 | 88 | [88] |
e e.e. = eee eeeeeeee.
Meeee 8 Meeeeeeeeeee ee Meeeeeeeee ee eee Meeeeeeee–Meeee Meeeeeee[88,88–88]
Meeeeeeee | M8 | Meeeeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
M M Me Me eMe |
MMM, MMMe8 MMM, (Me8MM)8M MMM, MMMe8 MMM, MMMe8 MMM, MMMe8 |
88 88 88 88 88 |
[88] [88] [88] [88] [88] |
||
M Me Me Me MMe |
MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 MMM, (Me8MM)8M |
88 88 88 88–88 88 |
[88–88] [88–88] [88,88] [88,88,88] [88] |
||
– | MMM, MMMe8 | 88 | [88] | ||
– | MMM, MMMe8 | 88 | [88,88] | ||
– | MMM, MMMe8 | 888 | [88–88] | ||
– – |
MMM, MMMe8 (8.8 eeeee), 8°M MMM, MMMe8 (8.8 eeeee), 88°M |
88e 88e 88e |
[88] [88] [88] |
||
M Me Me |
MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 MeM(Me)MMM, MMMe8 |
88 88 88 |
[88] [88] [88] |
e M8 = MMM; M8 = M.
e M8 = M; M8 = MMM.
e M8 = M8 = MMM.
Meeeee 8 Meeeeeeee ee 8-[Mee(eeeeeeeeeeeeeeeeeeee)eeeee]-8-(eeeeeeeeeeeeeeeeeeeee)eeeeeeeeeeee Meeee Meeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-(Meeeeeeeeeeee)eeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[88]
MMM (8 eeeee) eee M,M-eeeeeeeeeeeeeee (8 eeeee) eeee eeeeeee eeeee eeeeeee eeee MMMe8 (8 eeeee). Meeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eee 8 e ee 88°M eee eeee eeeeee ee 88–88°M. Meeee eeeeeeee eee 88 e, eee eeeeeee eee eeeeeeeee eeeee eee MMe, eeeeeeee ee 88–88°M, eee eeee eeee eeeee eeeee MeMM. Meeeeeeeee eeee MMMe8 eee eeeeeeeeee eeeeeeeeeeee (88 Meee) eeeeeeee eee eeeeeee; eeeee: 88%.
8,8-Meeeeeeeeeee-8-eeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeeeeee eeeeee eeeeeeeee eeee eeeee eeeeeeeee eeeee eeeeeee ee eeeeeeeee eeeee. Me ee eeeeeeeee eeeeeeeeeee ee eee eeeeeee.
Me MeM(Me)MMM (888 e, 8.88 eee) eeeeee ee ee eee–eeeee eeee, MMMe8 (88.8 e 8.88 eee) eee eeeee eeeeeeee eeee eeeeeeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeee ee eeeee ee ee eee 8 e eee eeee eeeeee ee 88–88°M eee 8 e eeeee eeeeeee eeeeeeee (88–88 Meee). Me eee eeeeeeeee eeeeee eeeeeee, 8,8-eeeeeeeeeeee (88.8 e, 8.88 eee) eee eeeee eee eeee ee 88°M. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeee ee 88°M eee 88 eee, eeeeee eeee eee eeeee, eee eeeeeee ee eeeee eee 8 e. Mee eeeeeeeee eeeeeee eee eeee eeeeeeeee eeee eeeeeee. Meeeee eeeeeeeeeeee eeeeeee eeeeeeee eeeeeee, eee eeeeeeeeee eeeeeeeee ee 88–88°M/88 Meee eeeeeeeee eeeeeeeee 8,8-eeeeeeeeeeee, eee eee eeeeeeeeee eeeeeeeee ee 888–888°M/88 Meee eeeeeeeee 8,8-eeeeeeeeeeee-8-eeeeeeeeeeee (eeeeeeeee); eeeee: 88% (eeeee ee eee eeeeee ee MeM(Me)MMM eeee) (88% eeeeeeeeeee eeeee ee eee eeeeee ee 8,8-eeeeeeeeeeee eeeeee eeeeeee).
8,8-Meeeeeeeeeeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[88]
MMMe8 (888 e, 8 eee) eee MeM(Me)MMM (888 e, 8 eee) eeee eeeeee ee e 8-M eeeee-eeeeee eeeee eee eeeeeee ee eeeee eee 88 eee. Me eeee eeeeeee eee eeeee, eeee eeeeeeee, 8,8-eeeeeeeeeeeeeeee (888 e, 8 eee) eeee 88 eee, eeeee eee eeeeeeee eeeeeeeeeee eee eeee ee 88°M ee e eeee eeeee eeee. Meee eeeeeeee eee eeeeeeee, eee eeee eee eeeeeee eee eee eeeeeee eee eeeeeee eee 8 e eeeeee eeeee eeee eee eeeeeeeeeee eeee ee 88°M. Mee eeeeee, eee eeeeeee eee eeeeeee ee eeeee eeeeeeeee eee eeee eeeeee eeeeee eeee eeeeeeee eeee eeee M8M (8.8 M). Mee eeeeeeeee eeeee eee eeeeeeeee eee eeeeee eeee eeee M8M. Mee eee eeee eee eeeeeeeee ee eeee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee), eee eee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeee eeeeeee (88 eM). Mee eeeeeeee eeeeeeee eeee eeeeeeeeeeee eee eeeeeeeee eeee e Meeeeee eeeee, eeeeee eee eeee eeeeeeee; eeeee: 888 e (88%); ee 888°M/8.8 Meee; ee 88–88°M.
Meeeee 8-Meeeee-8,8-eeeeeeeee-8-eeeeeeeeeeeeee (Meeee 8, Meeee 8):[88]
Me e eeee ee MMM (8.88 M, 8.88 eee) ee MM8Me8 (8 M) eee eeeeee eeeee MMMe8 (8.888 M, 8.88 eee). Mee eeeeeee eee eeeeeee ee 88°M eee 8.8 e. M eeee ee eeeeee 8,8-eeeeeeeee-8-eeeeeeeeeeeeee (888 e, 8.88 eee) ee MM8Me8 (8.8 M) eee eeeee eeee 88 eee. Meeee eeeee eeeeeeee eee 88 e, eee eeeeeee eee eeeeee eee eeeeee eeee eee eeeee (8 M). Mee eeeeeee eee eeeeeeeee eeee MM8Me8 (8.8 M), eee eee eeeeeee eeeee eee eeeeee eeee ee Me8MM8 (8 M) eee M8M (8 × 8 M), eeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeeeeee (MeMMe/eeeeee) ee eeee eee eeeeeeee ee e eeeee eeeee; eeeee: 888 e (88%); ee 888- 888°M.
8-[Mee(eeeeeeeeeeeeeeeeeeee)eeeee]-8-(eeeeeeeeeeeeeeeeeeeee)eeeeeeeeeeee (88):[88]
Me e eeee ee eee eeeee (8.88 e, 8.88 eeee) eee eeeeeeee (888 ee, 8.88 eeee) ee MMM (8.88 e, 88.8 eeee) eee eeeee MMMe8 (8.88 e, 88.8 eeee) eeeeeeee ee 8°M eeee 8–88 eee. Mee eeeeeee eee eeeeee eee 8–8 e ee 88°M eeeee eeeeeeeeee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeee ee MMM. Meeee eeeeeeeeee, eee eeeeeee eee eeeeee eeee eee eeeee. Meeee eeeeeeeeee eeee MeMMe, eee eeeeeee eeeee eee eeeeee eeee eeeee eee eeeee (MeMM8). Meeee eeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMMe 8:8). Meee eeee eee eeeeeeee 88 ee eeeee eeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.
References
[5] | Meeeeeeee, M.; Meeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 888. |
[14] | Meeeíe Meeeíeee, M.; Meeeíeee Meeeeee, M.; Meíe Meeeeee, M.; Me ee Meee Meeeee, M.; Meee Meeee, M.; Meeeíe Meeeee, M.; Meeeee, M.; Meeeeeeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
[15] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M.; Meeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[16] | Meee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M., MM 88 888 888, (8888); Meee. Meeee., (8888) 88, 88888. |
[17] | Mee-Meï, Me. Me.; Meeee, M. M.; Me, M.; Meeeeee, M.; Meee, M. M., Meee. Mee. Meee. Me., (8888), 8888. |
[18] | Meeeeeeee, M.; Meeeeeee, M. M., Meee. Meee. Meee, (8888) 88, 8888. |
[19] | Meeeeeeee, M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[20] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeee, M.; Meeeeee, M. M. M.; Meeeeeeee, M. M.; Meeeee, M., Meeeeee, (8888), 88. |
[21] | Meeeeeeee, M.; Müee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
[22] | Mee, M. M.; Meee, M. M.; Mee, M.; Meeeeeeeeeee, M.; Meeeeeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
[23] | Meeeeeeee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[24] | Mee-Meï, Me. Me.; Meeeeee, M.; Me, M. M. M., M. M. Meee. Meeeeee Meee. Mee., (8888) 888, 8888. |
[25] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[26] | Meeeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[27] | Meeeeee, M. M.; Meeeeäeeeee, M.; Meeeee, M. M.; Meeee, M.; Meeeeeee, M.; Meee, M.; Meeeeeeeee, M., Meeeeeeeeee, (8888) 88, 888. |
[28] | Meeeee, M.; Meee, M.; Meeee, M.; Meeeee, M., Meeeeeeee, (8888), 8888. |
[29] | Meeeeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeee, M., MM 88 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
[30] | Meeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[31] | Meeeeee, M., Mee. Meee. (Meee), (8888) 88, 888; Meee. Meeee., (8888) 88, 8888. |
[32] | Meeeeee, M. M.; Meeeeeee, M. M., Me.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[33] | Meeee, M.-e.; Meeeeeee, M.; Meeeeeee, M.; Meee, M., Meeeee. Mee. Meee. Meee., (8888) 88, 888. |
[34] | Meeee, M.; Meeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[35] | Meeeeee, M. M.; Meeeeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[36] | Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[37] | Meeeeeeee, Mee.; Meeeeeeee, Me. M.; Meeeeeeeeeeee, M. M.; Meeeeeeee, M. M., Meee. Meeeeeeeeee. Meeeee., (8888), 8888; Meee. Meeeeeeeee. Meeee. (Meee. Meeeee.), (8888) 88, 8888. |
[38] | Meeeeeeeeeeee, M.; Meeeeee, M.; Meeee, M., Meeeeee. Meee., (8888) 888, 888. |
[39] | Meeeeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[40] | Meeeeeeee, M.; Meeee, M. M.; Meeee, M. M., Me., M. Mee. Meee., (8888) 88, 888. |
[41] | Meeee, M.; Meee, M.; Młeeeeeeee, M., M. Meeee. Meee., (8888) 888, 888. |
[42] | Meeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[43] | Meeeeeee, M. M.; Meeee, M.M.; Meeeeee, M. M., Meee. M. Meee., (8888) 88, 888. |
[44] | Meeeeeeee, M.; Meeeeeee, M. M., Meeeee M. Meee., Meee. M, (8888) 88, 8888. |
[45] | Meee, M.; Meeeeeee, M.; Meeeeeeeeee, M.; Meeee, M.; Meeeeeeeeee, M.; Meeeeeeeee, M.; Me Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[46] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M. M.; Meeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[47] | Meeeeeeee, M.; Me-Meee, M.-M.; Meeee, M.-M.; Meeeeee, M.; Me Meeeeeeé, M.; Meeeee, M.-M., Meeeee. Mee. Meee. Meee., (8888) 88, 888. |
[48] | Meeeee, M. M.; Meeeee, M.; Meeeeeee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
[49] | Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[50] | Mee-Meï, Me. Me.; Meáe, Me.; Meeee, M., M. Meee. Mee., (8888), 888. |
[51] | Meeeeee, M.; Meeeeeee, M.; Meee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee-Meeeeeee, M.; Meeee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
[52] | Mee-Meï, Me. Me.; Meeee, M., M. Meee. Mee., (8888), 8888. |
[53] | Meeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meee, M. M.; Meee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 88. |
[54] | Meee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[55] | Meeee, M., Me. Meeeee. Meeeee., (8888) 88 (Me. 8), 88; Meee. Meeee., (8888) 88, 8888. |
[56] | Meeeeeee, M.; Meeeeeeeeeee, M., Meee. Meeee., (8888) 88, 888; Meee. Meeee., (8888) 88, 88888. |
[57] | Meee, M.; Meeeeeeeeee, M. M.; Meeeee, M. M., M. Meee. Meee., (8888) 8, 888. |
[58] | Meeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[59] | Meeeee, M.; Meeeeeee, M., Meeee. Meee., (8888) 88, 888. |
[60] | Meeeee, M.; Meeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
[61] | Meeeee, M.; Meeeeee, M.-M.; Meeeeee, M., Meee. Mee., (8888) 88, 888. |
[62] | Meeeee, M.; Meeeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 8888. |
[63] | Meeeee, M. M.; Müeeeeäee, M., M. Meeee. Meee., (8888) 88, 888. |
[64] | Meeeeeeee, M. M.; Meeeee, M. M., Me.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[65] | Meeeeeee, M. M.; Meeeeeee, M.; Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[66] | Meee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
[67] | Meeeee, M. M.; Meeeeeee, M. M., Me., M. Me. Meee. Mee., (8888) 88, 8888. |
[68] | Meeeee, M. M.; Meeeeeee, M. M., Me., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[69] | Mee-Meï, Me. Me.; Meáe, Me.; Meeee, M., M. Meee. Mee., (8888), 8888. |
[70] | Mee-Meï, Me. Me.; Meáe, Me.; Meeee, M., M. Meee. Mee., (8888), 8888. |
[71] | Meeeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[72] | Mee, M. M.; Mee-Meï, Me. Me.; Meeee, M. M., Meee. Mee. Meee. Me., (8888) 88, 8888. |
[73] | Meeeeee, M.; Mee-Meï, Me. Me.; Meeee, M., M. Meee. Mee., (8888), 8888. |
[74] | Meeee, M. M.; Meeeeee, M. M., Meeee. Meeeee., (8888) 88, 888. |
[75] | Meeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[76] | Meeee, M. M., M. Meee. Mee., (8888), 8888. |
[77] | Meeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeee, M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[78] | Meeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 8888. |
[79] | Meeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 88.
- 8.Meeeee-Meee, (8888) M 8, 88.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 8e, 88.