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Please login to access the full content or check if you have access via33.4.14.1.1 Method 1: Condensation of Arylaldehydes with α-Azido-Esters
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Collier, S. J., Science of Synthesis, (2007) 33, 544.
By far the most widely used approach to alkenyl azides is the base-mediated condensation between aldehydes (usually aryl- or hetarylaldehydes) and α-azidocarbonyl compounds. Many examples of such reactions involve the condensation of azidoacetate esters, e.g. 12, with aldehydes, e.g. 11, which give azidocinnamate esters, e.g. 13, and a range of these are given in Scheme 4. Many other examples are not discussed in detail, but are referenced here should further information be required. Most commonly these reactions are performed using alkoxide bases in alcohols at low temperatures. In the vast majority of cases, the resulting product has the azide unit and the aryl group cis to one another; however, some cases report formation of E/Z mixtures of isomers.[27,48] The two-step sequence of condensation of an azido ester with a benzaldehyde, followed by thermal cyclization to give an indole-2-carboxylic acid ester is sometimes known as the Hemetsberger–Knittel reaction.[51,129–131] With sterically hindered aldehydes, the condensation can be difficult, but use of a large excess of the diazo ester can facilitate the reaction. It has also been noted that methyl and ethyl azidoacetate are not particularly stable to the basic reaction conditions. Use of tert-butyl azidoacetate can provide improved yields in these reactions,[51] but usually use of a large excess of the methyl or ethyl azidoacetate is employed. When the reaction is run at low temperatures, dehydration of the intermediate azido alcohol may not take place to allow isolation. Subsequent treatment with dehydrating agents effects formation of the required alkenyl azide, and this approach is considered in Section 33.4.14.1.2.[27,51] Running the reaction at a slightly higher temperature usually allows condensation and dehydration in the same reaction,[27] although in the case of some N-unsubstituted carbazole aldehydes, the condensation gives only the azido alcohol, and attempted dehydrations to give the alkenyl azide have failed.[66]
Mee eeeeeeeeeee ee eeee eeeeee ee eeeeee-eeeeeeee eeeeeeeee eee eeee eeeeee eeeeeeeee eee eeee eeeeee eee eeeeeeeeee ee eeee eeee. Meeeeeee ee eeeeeee eeeeee ee eeeeeee eeeeeee eeeeeeeee eeeeeee: eee eeeee eeeeeeeee ee eeeeee eeeeeeeeeee eeeeee eeeeeeee eeeeeeee M,[888] (±)-eee- eee eeeee-eeeeeeeeee M[88,88] eee (±)-eee-eeeee-eeeeeeeeee M,[88] MMM-M,[88,88,888] MMM-M eeeeee eeeee,[888] MMM-MM,[88,88,888] eee MMM-MM eeeeee eeeee,[88,888] eee eeeeeeeee eeeeeeee eeeeeeeeee,[88] eee eeeeeeee eeeeeeeeeee,[88,88] eeeeeeeee ee eee eeeeee eeeeeeeee eeeeeeeeeeee M,[88] eeeeeeeeeeee M,[88] eee eeeeeeeeee M,[888] eee eeeeee eeeeee eeeeeeeee Mee-M-8,[888] eeeeeeeeee M eee M,[88] eeeeeeeeeeeee M[88] eee M,[88,88] eee eeeeeeee eeeeeee,[888] eeeeeeeeeeeee M,[88] eee e eeeeee eeeee eeeeeeeee ee eee eeeeeeeee eeeeeeeeee MM-8888.[88] Meeee eeeeeeeeeeee eeeeeee eee eeeeeeeee ee eeeeeeee MMM eeeeeeeee/β-eeeeeeeeeeeeeee eeeeeeeeee M888M,[88] eeeeeeeee ee eeeeeeeeeeee M,[88] eeeeeeeeeee(8–88) eeeeeeee,[88] eee 8,8,8-eeeeeeeeeeeeee eeeeee eeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeeeeee,[88] eee eee eeeeeeeeeee ee M,M-eeeeeeeeeeeeeeeeee eeeeeee.[888]
Me eee eeeeeeee ee eeeee, eeeeeeeeeeee eeeeeeeeeee eee eeeeeeee.[88,88,88–88,88,88–88,88,88,88,88–88,88,88,88–88,88–88,88–88,88–88,88,88,88–888,888,888,888,888,888–888,888,888,888,888,888,888] Meeee eeeeeeee eeeeeeeee eeee ee eeeee eeeeeeeee eeeeeee 8M-eeeeeeee-8-eeeeeeeeeeee,[88] eeeeee-8-eeeeeeeeeeee,[88] eee eeeeeeeeeeee-8-eeeeeeeeeeee.[88] Meeeeeeeeeeeee eeeeeeeee eeee eeee eeee eeee eeeeeeeeeee, eeee eeeeeeee eeeeeeeee eeeeee-8-,[88,888] eeeeee-8-,[88,88,888,888,888] eee eeeeee-8-eeeeeeeeeeeee,[88,88,88,88] eeeeeeeeeeeee-8-eeeeeeeeeeee,[88,88,888] eeeeeeeeeeeeeeeeeeeeee,[88,888,888] eeeeeee-8-eeeeeeeeeeee,[888] 8-eeeeeeeeeee,[88,88,88,888,888–888] eeeeeeeee-8-[88,88,88,88,88,88,88,888,888,888] eee eeeeeeeee-8-eeeeeeeeeeeee,[88,888] eeeeeeeeeee-8-eeeeeeeeeeee,[888] eeeeeeee-8-eeeeeeeeeeee,[88,888] eeeeeeeeeeeeeeeeeeeeee,[88,888] eeeeeeee-8-eeeeeeeeeeee,[88,88,88,888] eeeeeeeeee-8-eeeeeeeeeeee,[88,888,888] eeeeeeeeeeeeee-8-eeeeeeeeeeee,[88] eeeeeeee-8-,[888] eeeeeeee-8-,[888] eee eeeeeeee-8-eeeeeeeeeeeee,[888] β-eeeeeeeee eeeeeeeeeeeee,[88] eeeeeeee-8-eeeeeeeeeeee,[88] eeeeeee[8,8-e]eeeeeeee-[88,88,888] eee eeeeeee[8,8-e]eeeeeeeeeeeeeeeeeeeeeee,[88,888] eee(eeeeeeeeeeee) eeee eeeeee eeeeeee,[88] eeeeeeeee-8,8-, eeeeeeeee-8,8-, eee eeeeeeeee-8,8-eeeeeeeeeeeeeee (eeee eeeeeeeeeeee ee eeeeee eee ee eeee eeeeeeeee),[88] eee eeeeeeeeeeeeeeeeeeeeee eee eeeeeeeee-8,8-eeeeeeeeeeeeeee.[888,888–888] Meeee ee eeee e eeeeee ee eee eee ee e eeeeee eeeeeeee ee eeeee eeeee eeeeeeeeeeeee: eeeeeeeee ee e 8-eeeeeeeeeeeeeeee eeee eeeee eeeeeeeeeeee eeeee eeeeeeee eeeeeeeeee eeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeeee, eeeeeee e eeeeeeeeee eeee ee eee eeeee eeeeeeee.[888]
Meeeee 8 Meeeeeeeeeeeee Meeeeeeeeee eeee eee Meeeeeee ee Meee Meeeeeeee eeee Meeeeeeeeeeee[88,88,88,88,88,88,88,88,88,88,88,88,88,888,888,888,888,888,888,888]
| Me8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
 |
Me | MeMMe, MeMM, 8–8°M, 8.8 e | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M, 8 e | 88 | [888] |
| |
Me | MeMMe, MeMM, −88°M, 8 e | 88 | [888] |
| |
Me | MeMMe, MeMM, 8°M, 8 e | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M | 88 | [88] |
| |
Me | MeMMe, MeMM, MMM, −88°M | 88 | [88] |
| |
Me | MeMMe, MMM, −88 ee 8°M, 8 e | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M | 88 | [888] |
| |
Me | MeMMe, MeMM, −88°M, 8 e | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M | 88 | [888] |
| |
Me | MeMMe, MeMM, −88°M | 88 | [888] |
| |
Me | MeMMe, MeMM, 8–88°M, 88 eee | 88 | [88] |
| |
Me | MeMMe, MeMM, 8–88°M, 8 e | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M | 88 | [88] |
| |
Me | MeMMe, MeMM, −88 ee 8°M, 8.88 e | 88e | [888] |
| |
Me | e-MeMM, e-MeMM, MeMM, −88 ee 88°M, 8 e | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M, 8.8 e | 88e | [88] |
| |
Me | MeMMe, MeMM, eeeeeeee, −8 ee 8°M, eeee 8°M, eeee ee | 88 | [88] |
| |
Me | MeMMe, MeMM, −88°M | 88e | [888] |
| |
Me | MeMMe, MeMM, −8°M, 8 e, eeee 8°M, 88 e | 88 | [88] |
e Meeee eeeee.
e Meeee ee eeeeeee.
e Meeee ee eeeeeee. M eeeee ee 88% eee eee eeeeeeeee eee eeee eeeeeeee.
Meeeeeee ee eeee eeeee eeee- eee eeeeeeeeeeeeeeee eee eeee ee eeeee eeeeeeeeeeeeeee, eeeee eeeeeeeee eee ee eeee (Meeee 8). Meeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeee eeeee eeeeee (eeeeeee 8–8)[888–888] eee eeeeeee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeee eeeeee eeeeeeee eeeee 8-eeee-8M-eeeeeee-8-eeeeeeeeeeee. Meeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eee eeee ee eeee (eeeee 8),[888] eee, ee eeee eeee, eeeeeeeeeee eeeee eeee ee 8,8′-eeeeeeeeee. Meeeeeeeeeeeeee eeeeeeeee eee ee eeee (eeeee 8),[888] eeeeee eeeeeee-8-eeeeee eeeee eeeeeeeeee ee eee eeeeeeeee eeeeeee eeeee eeee ee eeeeeeeeeeeeeeee eee eeeeeeeee eeee eeeeeeeeeee. α-Meeee eeeeeee eee eeee ee eeee ee eeeeeeeeeeee eeeeeeeee eeee eeeeeeeee;[888,888–888] ee eeee eeee, eee eeeeeeeee eee eeeee eeeeeeee ee eeeeeeeeeeee eeeeeee, eeeeee eeee ee eeeeeeee eeee, eeeeee eee eeeeeeeeeeeee eeeeeee eeeeeee. Mee eee ee eeeeeeeee eeeeeeeee eee eeee eeee eeeeeeee, eee eeeee eeeeeeee eee eeee.[88,888,888,888,888]
Meeee 8 Meeeeeeeeeeee ee Meeeeeeee eeee Meeeeeeeeeeee Meeeeeeee[88,888,888,888–888,888]
| Meeee | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| 8 | |
MMe | MeMMe, MeMM, −88°M ee ee, 8.8 e | 88 | [888] |
| 8 | |
MMe | MeMMe, MeMM, −88°M ee ee, 8.8 e | 88 | [888] |
| 8 | |
MMe | MeMMe, MeMM | 888 | [888] |
| 8 | |
MMe | MeMMe, MeMM, −88 ee −8°M, 8 e | 88e | [888] |
| 8 | |
MMe | MeMMe, MeMM, −88°M, 8 e | 88 | [888] |
| 8 | 8-MeMM8M8 | |
eeeeeeeeeeee eeeeeee, MeMM, ee, 88 e | 88 | [888] |
| 8 | Me | |
eeeeeeeeeeee eeeeeee, MeMM, ee, 88 e | 88 | [888] |
| 8 | 8-MeMM8M8 | 8-Mee | eeeeeeeeeeee eeeeeee, MeMM, 88–88 e | 88 | [888] |
| 8 | Mee | 8-MeM8M8 | eeeeeeeeeeee eeeeeee, MeMM, 88–88 e | 88 | [888] |
| 88 | 8-M8MM8M8 | 8-MeM8M8 | eeeeeeeeeeee eeeeeee, MeMM, 88–88 e | 88 | [888] |
| 88 | 8,8-Me8M8M8 | 8-MeM8M8 | eeeeeeeeeeee eeeeeee, MeMM, 88–88 e | 88 | [888] |
| 88 | Me | 8-MeM8M8 | eeeeeeeeeeee eeeeeee, MeMM, ee, 88 e | 88 | [888] |
| 88 | Me | 8-MeM8M8 | eeeeeeeeeeee eeeeeee, MeMM, ee, 88 e | 88 | [888] |
| 88 | |
8-MeM8M8 | eeeeeeeeeeee eeeeeee, MeMM | –e | [88] |
e Meeee eeeeeeeeeee.
e Mee eeeeeeee.
Meeeee 8 eeeeeeeeeee eeee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee 88 eeee eeeee eeeeeeeeeeee ee eeee eee eeeeeeeeeeeeeee 88.[88]
Meeeee 8 Meeeeeee ee Meeeeeeee eeee Meeee Meeeeeeeeeee[88]
| Me8 | Meeee (%) | Mee |
|---|---|---|
| 8-eMeM8M8 | 88 | [88] |
| 8-Mee | 88–88 | [88] |
| Mee | 88 | [88] |
| 8-MeM8M8 | 88–88 | [88] |
| 8-MeMM8M8 | 88 | [88] |
| 8,8-Me8M8M8 | 88 | [88] |
| |
88 | [88] |
| |
88 | [88] |
| |
88 | [88] |
Meeeeeeeeeee Meeeeeeee:
Meeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
Me (8.88 e, 8.88 eee) eee eeeeeeeee ee MeMM (88 eM) eee eee eeee eee eeeeee ee −88°M. M eeeeeee ee eee eeeeeeee 88 (8.88 eee) eee eeeee eeeeeeeeeeee (88.88 e, 8.88 eee) eee eeeee eeeeeeee eeee eeeeeeee ee e eeee eeee eeeeeeeeee eee eeeeeeeeeee eeeee −88°M. Me eee eeeeeeee eee eeeeeeeee ee eeeee eeeeeeeeeeee, eeeeeeeeee MeMM ee MMM eee eeeee ee eeeeeee eeeeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeeee ee ee. −88°M eeeee MMM eeeeeeee eeeeeeeee eeee eee ee eee eeeeeeee eee eeee eeeeeeee (8–8 e), eee eee eeeeeee eee eeee eeeeeee ee eeee ee ee. Mee eeeeeee eee eeeeee eeee eee eeeee eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee Me8M eeeeeeee eeee eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeee eeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee ee eeeee; eeeee: 88–88%. Meeee eeeeeee eeeeeeeee eeee eeee eeeeeeeee eeeee 88 eeeee ee eee eeeeeeeeeeee ee eeeeeeee eee eeeeeeee eeeeee.
References
| [10] | Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
| [23] | Meeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [24] | Meeeeeeeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meee, M., Meeeeee. Meee., (8888) 888, 888. |
| [25] | Meeeee, M. M. M.; MeeMeeeee, M.; Meeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [26] | Meeeee, M. M.; Meeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [27] | Meeeeee, M.; Meeeeeee Meeeeeee, M.; Meeeee, M. M.; Meeeee, M. M.; Meeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [28] | Meeeeeeeee, M. M.; Meeee, M. M.; Me, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [29] | Meeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
| [30] | Meeeee, M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meee, M. M.; Meeee, M. M.; Meeeee, M. M. M.; Meeee, M. M.; Meeee, M. M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [31] | Mee, M. M.; Meeeeee, M.; Meeee, M.; Meeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [32] | Meee, M.; Máeeee, M.; Meeeíe, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [33] | Meeeeeeee, M.; Meeeeee, M. M.; Meeeeeeeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M. M.; Meeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [34] | Meeeee, M. M. M.; MeMeeeee, M. M., Meee. M. Meee., (8888) 88, 888. |
| [35] | MeeMeee, M. M.; Meee, M.; Meeeee, M. M., Meee. M. Meee., (8888) 88, 888. |
| [36] | Meeee, M.; Me, M.-M.; Meeee, M.-M.; Meee, M.-M.; Meee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
| [37] | Meeeee, M. M.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [38] | Meeeeee, M.; Meeeee, M. M.; Meee, M.; Meee, M., Meeeeeeeeeee, (8888) 88, 88. |
| [39] | Meeee, M.; Me, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [40] | MeeMeee, M. M.; Meeeeee, M. M., Meee. M. Meee., (8888) 88, 888. |
| [41] | Meeeeeeeee, M. M.; Meeeee, M. M.; Meeeeeeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [42] | Meeee, M. M.; Meeeeeee, M.; Meeeeeeeeee, M.; Meeee, M. M.; Meeeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [43] | Meeee, M. M.; Meeeeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [44] | Meeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [45] | Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [46] | Meeeeeee, M. M.; Meeeee, M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [47] | Meeeeeee, M. M.; Meeee, M. M.; Meee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [48] | Meeeeeee, M. M.; Mee Meee, M.; Meeeeeee, M.; Meeeeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [49] | Meeeeee, M., Meeeeeeee, (8888), 888. |
| [50] | Meeeeee, M.; Meee, M.; Meeeeeee, M., Mee. M. Meee., (8888) 88, 8888. |
| [51] | Meeee, M.; Meeeeeeee, M.; Meeeeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [52] | Meeee, M. M.; Meeee, M. M.; Meeeee, M. M., Meeee. Meeeee., (8888) 88, 888. |
| [53] | MeeMeee, M. M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [54] | Meeee, M.; Meeeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [55] | Meeee, M. M.; Meee, M.; Meeee, M. M.; Meeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [56] | Meeeeeee, M. M.; Meee, M. M.; Meeeeeee, M. M.; Mee'eeeeeeee, M. M., Meee. M. Mee. Meee. (Meee. Meeeee.), (8888) 88, 8888. |
| [57] | Meeee, M. M.; Meeeee, M.; Meeeee, M.; Meeeeeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeee, M.-M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [58] | Meeeeeee Meeee, M.; Meee, M.; Meeeee Meee, M.; Meeeeee, M.; Meeee, M. M.; Me Meeee, M.; Meee Meeee, M.; Meeeee Meeee, M. M. M. M.; Meeeee, M.; Meeee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [59] | Meeeee, M.; Meeee, M.; Meee, M.; Áeee-Meeeeee, M.; Áeee, M.; Máeeáeee, M.; Meeeáee, M.; Meeee-Meeeee, M.; Meeó, M.; Meee, M.; Meeeee, M.; Meee, M.; Meeeee, M.; Meeáee, M., Meeeee. Mee. Meee. Meee., (8888) 88, 8888. |
| [60] | Meee, M.; Meeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeee. Mee. Meee. Meee., (8888) 88, 8888. |
| [61] | Meeee, M.; Méeeee, M.-M.; Meeeee, M.; Meeeeeeeee, M., Mee. M. Mee. Meee., (8888), 8888. |
| [62] | Meee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeeeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [63] | Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeee, M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
| [64] | 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. |
| [65] | Meeee, M. M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
| [66] | Meeeeeeee-Meeeeeee, M.; Meeeeeee-Meeeee, M.; Meeeeeee-Meeeeee, M.; Meeee, M. M.; Meeeeeeee-Meeeee, M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [67] | Meeeee, M. M. M.; Meeee, M. M.; Meee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8. |
| [68] | Meeeee, M. M. M.; Meeee, M. M.; Meee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [69] | Meee, M.; Meeeee, M. M. M.; Meeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [70] | Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [71] | Meeeee, M. M.; Meeee, M. M.; Meee, M. M.; Meee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [72] | Meeeee, M.; Meeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [73] | Meeeee, M. M. M.; Meeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [74] | Meeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [75] | Meeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [76] | MeeMeeeee, M. M.; Meeee, M. M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [77] | Meeeee, M. M.; Meeee, M. M.; Meee, M. M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [78] | Meeeee, M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [79] | Meeeee, M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [80] | Meeee, M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [81] | Meeeeee, M. M.; Meeeeeeee, M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., Mee. Meeeee. Meee., (8888) 8, 888. |
| [82] | Meeeee, M. M.; Meeee, M. M.; Meee, M.; Meee, M. M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [83] | Meee, M. M.; Meeeee, M. M.; Meeeeeeee, M.; Meeeeee, M. M.; Meee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [84] | Meeeeeeee, M. M.; Meee, M. M.; Meeeeeeee, M. M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [85] | Meeeeee, M.; Meeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [86] | Meeee, M.; Meeeee, M.; Meeeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [87] | Meeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [88] | Meeee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [89] | Meeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [90] | Meeee, M. M.; Meee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [91] | Meeee, M. M.; Meeee, M. M.; Meee, M. M.; Meee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [92] | Meeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [93] | Meeeeee, M. M.; MeeMeeeee, M. M.; Meeee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [94] | Meeeeeeeee, M.; Meeeee-Meeeeee, M.; Meee, M.; Meeee, M.; Méeéeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [95] | Meee, M.-e.; Meeeeeee, M.; Meeee, M.; Meeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
| [96] | Meee, M.-e.; Meeeeeee, M.; Meeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
| [97] | Meeeeš, M.; Meeee, M.; Meeeeč, M.; Meeeeeeee, M.; Mešeee, M., Meeeeeeeeeee, (8888) 88, 888. |
| [98] | Meeee, M. M., Me.; Meeee, M. M.; Meeeee, M.; Meeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [99] | Meeee, M. M., Me.; Meee, M.; Mee, M., Meeeeeeee, (8888), 8888. |
| [100] | Meeee, M. M., Me.; Meeee, M. M.; Meeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [101] | Meeeeee, M., Meeeeee. Meee., (8888) 888, 8888. |
| [105] | Meeeeee, M.; Meeeeee, M.-e.; Meeeeeeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [106] | Meeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [108] | Meeeee, M.; Meeeeeee, M. M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [109] | Meeeee, M.; Meee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |
| [110] | Meeeeee, M.; Meeee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [111] | Meeeeeeee, M. M.; Meee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [112] | Meeeee, M.; Meeeee-Meeee, M.; Meeeeeee, M. M., Meeeeee, (8888), 88. |
| [113] | Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [114] | Meeeeeeee, M. M. M.; Meeee, M. M.; ee Meeee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 88. |
| [115] | Meeeee, M.; Meeeeeíe, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [116] | Meeeee, M.; Máeeeee, M.; Meeóe, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [117] | Meeeeeeee, M.; Meeeeee, M. M.; Meeee, M.; Meeeeeeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [118] | Meeeee, M.; Meeeeeíe, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8. |
| [119] | Meeeee, M.; Meeeeeee, M. M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [120] | Meeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [122] | Meeeee, M.; Meeeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [123] | Meee, M.-M.; Mee, M.; Meee, M.-M.; Mee, M.-M.; Mee, M.-M., Meeee. Meeeee., (8888) 88, 8888. |
| [124] | Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [125] | Múeóe, M.; Meáeeee, M.; Meeáee, M.; Meöeee, M.; Meeeeee, M.; Meeáe, M., Mee. M. Mee. Meee., (8888), 8888. |
| [126] | Mee, M.; Meee, M.-M., Meeee. Meeeee., (8888) 88, 88. |
| [127] | Meeeee, M.; Meeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [128] | Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 88. |
| [129] | Meeeeeeeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeee. Meee., (8888) 888, 8888. |
| [130] | Meeeeeeeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeee. Meee., (8888) 888, 888. |
| [131] | Meeee, M. M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 88–88. |
| [132] | Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [133] | Meeeeeee, M. M.; Meeeee, M.; Meee, M. M., Meeeeee, (8888), 8888. |
| [134] | Meeeee, M.; Meeeee, M.; Meñóe, M.; Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeíeee, M.; Meeeeeee, M.; Meeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 888. |
| [135] | Meee, M. M.; Mee, M.; Mee, M. M.; Mee, M. M., Meee. Meee. Meee., (8888) 88, 888. |
| [136] | Meeeeeee, M.; Meeeeeeeeee, M.; Meeee, M., Meee. Mee., (8888) 88, 888. |
| [137] | Meeeeeeeeee, M.; Meeee, M.; Meeeeeeeeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 888. |
| [138] | Meeeeeeeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeee, M.; Meeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888. |
| [139] | Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M., Meee. Meee. Meee., (8888) 88, 888. |
| [140] | Meee, M.; Meeeeee, M.; Meeeeeee, M., Meee. Mee. Meee. Me., (8888), 8888. |
| [141] | Meeee, M.; Meeeeeee, M. M., Meeeeeeeee. Meeeee., (8888) 8, 888. |
| [142] | Meeeee, M.; Meeeeeeeeeee, M. M.; Meeeeeeeeee, M.; Meeeeee, M. M.; Meeeeee, M., Meee. Meee. Meee., (8888) 888, 888. |
| [143] | Meeeeeeeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888. |
| [144] | Me, M.-M.; Meee, M.-M., Meeeee Meeee, (8888) 88, 888. |
| [145] | Me, M.-M.; Meee, M.-M., Meeeeeee Meeeee, (8888) 88, 888. |
| [146] | Meeeeee, M.; Meeeee, M.; Meeeee, M., MMMMMMM, (8888) e, 88; eeee eeeeeeeee eeeeee, eee.eeeee-eee.eee. |
| [147] | Meeee, M. M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meee, M.; Meeeee, M.; Meeeeeee, M.; Me Meeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [148] | Meeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meee, M.; Meee, M.; Meee, M. M.; Mee, M.; Meeeeeeee, M.-M.; Meee, M.; Meee, M.-M.; Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Mee eee Meeee, M. M. M., Meeeee. Mee. Meee. Meee., (8888) 88, 888. |
| [149] | Meeeeeeeeeee, M.; Meeee, M.; Meeeeeeeeeee, M., M. Meee. Mee., Meeee., (8888), 888. |
| [150] | Meee, M.; Meeee, M. M.; Meeee, M. M.; Meeeeee, M.-M., Meeeeeeeeee, (8888) 88, 8888. |
| [151] | Meeeee, M.; Meeee, M.; Meeeeee, M. M., Meeeeeeee, (8888), 8888. |
| [152] | Meeeeee, M.; Meeeeeeeeeee, M.; Meeeeeee, M., Meeeeee. Meee., (8888) 888, 888. |
| [153] | Meeeeee, M.; Mee, M. M., Meeeeee. Meee., (8888) 888, 888. |
| [154] | Me Meeee, M.; Meeeeee, M.; Meeeee, M.; Meeeee, M.-M.; Meeeeee, M. M. M.; Meeeee Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [155] | Má, M. M.; Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [156] | Meeeeee, M.; Meeee, M., M. Meeeeeeeeee., M, (8888) 88, 8888. |
| [157] | Meeeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [158] | Meeeeeeeeeee, M.; Meeeeee, M., Meeeeee. Meee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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