You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via8.1.1.3.3 Variation 3: Reduction of π-, Strained C—C, or C—X Bonds α to a Carbonyl Group
Please login to access the full content or check if you have access via
Dieter, R. K., Science of Synthesis, (2006) 8, 113.
The dissolving metal reductions of α,β-enones, α,β-cyclopropyl ketones, or α-heteroatom-substituted ketones generates an intermediate enolate regiospecifically,[577] thereby coupling the synthetic power of enolate chemistry with the reduction procedure. Lithium metal reductions of α,β-enones and α,β-cyclopropyl ketones are widely used in synthesis for the control of stereochemistry, regiochemistry, and the stereoselective introduction of a β-methyl substituent in case of the latter functionality.
Mee eeeeeeeee ee α,β-eeeeee ee eeeeeeee ee eeeeeee eeeeeeeeee eee-eeeeeeee eeeeeeeeee eeeeeeeeee eeeeeee e eeeeeeeeee eeeee (eeeeeee eeeee) eee eeeeeee, eeeeeeeeeee ee ee eeeeeee eeeee.[888,888,888] Mee eeeeeee ee eeeeeeeeeeee eeeee ee ee eeeeeee eeeeeeeeee ee eeeeeee eee eee eee ee eeee eeee 8 eeeeeeeeee ee e eeeeeeee eeee eeeeeee ee eee eeeeeeeeeee ee eee eeeeeee eee eeeee ee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeee. Mee eeeeeee eee eeee eeeeeee eeee eeeeeeee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eee β-eeeeee eeee eeeee Meeeeee eeeeeeeeee (e.e., eeeeeee–eeeeeeeeeee–eeeeeeee).[888] Meeeeeeee, 8 eeeeeeeeee ee eeeeeee ee eeeeeeee ee eeeeeeeee eee eeeeeee eeeeeeeeeeee eee eeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeee eeeeeeeeeeee. eeee-Meeee eeeeeee[888] ee eeeeeeeee eeeeeeeee eeeee eeeeeeee eee eeeeeee eeeeeee eeeeeeeee eeeeeeee eee eeee ee eeeeeeee ee eeeeeee eee eeeeeeee eee eeeeeeeeeeeee. Meeeeee eeeee eee ee eeee ee eeeeeeeeeeeeee eeeeeeeeee eeee eeeeeee eeeeee (eeeeeee–eeeeeee) ee eeeeeeee.[888] Mee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeee ee eee eeeee eee-eeeeeeee eeeee ee eeeeeeeee eeeee eeeeeeeeeee (eeeeeee ee eeeee-eeeee eeeee) eee eeeee eeeeee ee eeeeee eee eeee eeeeeeeeeeeeeeeee eeeeee eeeeeee,[888,888] eeeee eee ee eeeeeeeeeeee eeeeeeeee (Meeee 88) eeee eeeee eeeeeee,[888–888] eeeee (e.e., 888)[888–888] eee eeeeee eeeeeee,[888,888] α-eeee eeeeee,[888] eeeeeeeeeeeee (e.e., 888),[888] ee eeeeeeeeeeee.[888] Meeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeee eeeeeee ee eeeeee eee eee eeeeeeee eeeeeeeeeee ee eee 8,8-eeeeeeee eeeeee ee eeee ee eeeeee eeeeeee eeeeeee eeeeeeeeeeeeeee.[888] Meeeeeeeeeeeeee ee, eeeeeeeee, eeeeeeeee ee eee eeeeeeeeeeee eeeeeee eeeeeeeee ee eee ee eee ee eeee 8,8-eeeeeeee eeeee eeee eeeeeeeee eeeeeeeeeee ee e eeee eeeeee eeee eeeeeeeee eeeeeeeeeeeee.
Meeee 88 Meeeeeeeee Meeee Meeeeeeeee ee α,β-Meeeee eee Meeeeeeee[888,888,888,888,888,888–888]
| Meeeeeeee | Meeeeeeeee | Meeeeee(e) | Meeee (%) | Mee |
|---|---|---|---|---|
 |
8. Me, eee MM8, Me8M 8. M8M=MMMM8Me |
|
>88 | [888] |
| |
8. Me, MM8, e-MeMM, Me8M 8. MeM8MMM, Me8M |
|
88 | [888] |
| |
8. Me, MM88. MeMM8Me 8. Meeeee MM8, eeee Me8M, Me8M |
|
88e | [888] |
| |
8. Me, eee MM8, Me8M 8. MM8Me |
|
88 | [888] |
| |
8. Me, MM8, M8M, MMM 8. MeM |
|
88e | [888] |
| |
8. Me, eee MM8, Me8M 8. MM8Me |
|
88e | [888] |
| |
Me, MM8 | |
88 | [888] |
| |
Me, MM8, Me8M, −88°M | |
88 | [888] |
| |
8. Me, MM8, MMM 8. MM8Me |
|
88 | [888] |
| |
8. Me, M8M(MM8)8MM8, MeM(MM8)8MMe8. Meeee eeeeeeeee | |
88 | [888] |
| |
Me, MM8 | |
88 | [888] |
| |
8. Me, MM8, MMM 8. M8M=MMMM8M |
|
–e | [888] |
| |
8. Me, eeeeeeeeeee (8 eee%), Me8MM8. M8M | |
88 | [888] |
e M8 = M, Me.
e Me 88%.[888]
e M8 = MM=MM8; 88% eeeee eee M8 = M≡MM.
e Mee eeeeeeee.
Mee eeeeee-, eeeee-, eee eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeee ee Meeee 88. Meeeeeeeee (e.e., 888)[888] eee eeeeeeeee (e.e., 888)[888] eee ee eeeeeeee ee eeee eeeeeee eeeeee eeee eeeeeeee eeeeeeeeeeeee. Meeeeeeeeeeee, eee eeeeeee eee ee eeeeeee ee eee eeee eeeeeee (e.e., 888)[888] eee eee eeeeeeeeeeeee eeeeeee eeeeeeeeeee ee e eeeee eeee. Meeeeeeee ee eeeeeeeeeeee eeeeeee eeeeeeee eee eeeeee ee eeeeeeeeee eeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeeee eeeeeeeeee eeeeee eeee ee eeeeeee,[888] eeeeeeeee eeeeee (e.e., 888),[888] eee eeeee ee eeeeeeeee eeeeeeee ee eeeeee.[888] Me eeeeeeeeeeeeee eeeeeeeee eeeeeeeeee, eeeeeeee ee e eee-eeeee eeeeeeeee eeeeeeee, eeeee eeeeeee eeeeee eee eeeee ee eeeeeee eeeeeeeeeeee, eeeee eee eeeeeeeee eeeeee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eeeee eeeeeeee.[888] Meeeeeee eeeeeeeeee eeeeeee eeeeee eee eeeeee ee eeeeeeeeee eeeee eeeeeeeeee (e.e., 888).[888] Meeeeeeee ee eeeeee[888] ee eeeee-eeeeeeeeee[888] eeeeee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeeeee. Me eeeeeeeeee ee eeeee-eeeeeeeeee eeeeeeeeeeeeeeeee, eee eeee-eeeeeeeeeee eeeeee eeee ee eeeeeeeeeeeeeeee eeeeeee.[888] Me eee eeeeeee ee eeeeee eeeeee, α,β-eeeeee eee ee eeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee eeeee eeeeeeeee,[888] eee eeeeeee eee eeeeeeeeeee eeeeeeee (e.e., 888).[888] Meeeeee eeeeeeee ee eee eeeeeeeeee eeeee eeeeeeee ee eee eeeee eeeeeee eeeeeeeee ee ee eeeee ee eee eeeeeeee ee e eeeee eeeeeeee.[888] Meeeeeee eeeeee eee ee eeeeeee eeeee eeee eeeeee (e.e., 888),[888] eee eeeeeeeeeeeeee eeeeeeeee ee eeeeee ee eee eeeeeeee ee eeeeee eee eeeeeee (e.e., eeeeeeeee ee 888 ee eeee 888) eee ee eeeeeeee ee eee eeeeeeeeeeee.[888] Mee eeeee ee eeeeeeeeeeeeee eeeeeee eeee eeeeeee ee ee α,β-eeeeeeeeeee eeeeee (e.e., 888),[888] eeeeeeeee eeeeeeee[888] eee eeeeeeeeeeeeee[888] eeeee. Meeeeee[8.8.8]eeeeee eeee eeeeee eee-eeeee eeeeeeeeeeeee (e.e., 888),[888,888,888–888] eeeee-eeeee eeeeeeeeeeeee,[888,888] ee eeeeee eeeee eeeeeeee[888] ee eee eee eeee eee eeeeee eeee ee ee eee eee-eeeeeeee eeee, eeeeeeeee eeee eee eeeeeeeeeeee eeeeeee, e.e. eeeeeeeeee eeeeeeeeeeee. eeeee-Meeee eeeeeeeeeeeee eee eeeeeeeee eeeeeeee eeee eee eeeeee eeee ee ee eee eeee-eeeeeeee eeee (e.e., 888).[888,888–888] Meeee eeeeeee eeeee ee eee eeeeeeeeeeee eeeeeee eeeeeeeeee ee ee eeeeeeee eeeeeee ee 8,8-eeeeeeee eeee eee eee ee eeeeeeeeeee eeee eeee eeeee. Meeeeee[8.8.8]eeeeee eeeeeee eeee, ee eeeeeeee, eee-eeeee eeeeeeee (e.e., 888).[888,888] Meeeeee eeeeee 888 eee eeeeeee eeeeeeeee[888] ee eeeeeeeee eeeeeeeeee[888] eee eee eeeeeee ee eeeeee 888 eee ee eeeeeee eeee eeeeee eeeeeeeeeeeee ee eeeeee γ-eeeeeeeeeeeeee eeeee eeeeee.[888]
Mee eeeeeeeeeeee eeee eee ee eeeeeee ee eeeeeeeeee eeeeee ee eee eeee eeeeeeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeee (e.e., eeeeee eeeeeee,[888] eeeeeee eeeeeee,[888] ee eeeeee[888]) eee eee eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeeee eeeeeee eee eeeee ee eeeeeeeee.[888,888] Mee eeeeeeeee eeeeeeee eee eee eeeeee- eee eeeeeeeeeeeee eeeeeeeeeeee ee e eeeeee eeeeeeeeeee (Meeee 88). Meeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeeee eeeeeee eeeeee eee eee eeeeeeeeeeeeee eeeeeeeeeeee ee e eeeeee eeeee ee eee M8 eeeeeeee (e.e., 888),[888] eeeeeee ee eeeeee eee- ee eeeee-eeeee MM eeeee. Mee eee-eeeee eeeeeee ee eeee eeeeeee eeeeeeeee eee e eeeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeee eeeeeeee. Mee eeeeeeeeeee eeeeee ee eeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee ee eeeeeeee eeee (e.e., 888),[888] eeeeeeee eeeeeeeee eeeeeee (e.e., 888)[888] eee eeeeeee eeeee eee eeeeeeee eeeeeeeeee. Mee eeeeeeeeeeee eeee eee ee eeee ee eeeeee eeeeeeeeeee eeeeeee eee eeee eeeeeee ee e eeeee eeeee (e.e., eeeeeeee ee 888 ee eeee 888)[888] ee eeeeeee ee eeeeeeeee e eeeeee eeeeeeeeeee eeee e eeeeeeeeee eeeeeeee eeeeeeee (e.e., 888)[888] eee eeeee eeeeeee eeeeeeeee eeeee. Meeeeeeee ee 888 eeee eeeeeee eeeee eeeeeee eeeeeeeeeee eeeeee eeeeeeee ee eeee ee e eee-eeeeeeeeeeeee. Mee eeeeeee eeeee ee eeeeeeeeeeeeeee eeeeeeeee ee eee eeeeee eeeeeeeeee, eeeeee eee eeeeee eeee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeeee eeee eeeeeeee. Meeeeeee eee eeeeeeee eeeeeeee ee eeeeeeeeeeeeee, eee eeeeeee eeeeeeeeee eee eeee eeeeeeee ee eeeeeeeeeeeee (e.e., 888).[888] Meee eeeeeeeeeeeee ee eee eeeeee eeeeee, eeeeeeeeeee ee eeeee eeeeeeee eeee Meeee eeeeeee.[888] Meeeeeeee ee 888 eeeeeeee ee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeee eeee eeeeeeee, eeeeeee ee eeee eee eeee eeeeeeeee eee β-eeeeeeeeee eeeeeeee.[888] Meeeeeeeee eeeeeee eee eeee eeeeeee ee eeeeeee–eeeeeee.[888]
Meeee 88 Meeeeeeee Meeeeeee ee Meeeeeeeeee Meeeeee[888,888–888,888]
| Meeeeeeee | Meeeeeeeee | Meeeeee(e) | Meeee (%) | Mee |
|---|---|---|---|---|
| |
Me, MeMM8, Me8M | |
88 | [888] |
| |
8. Me, MM8, Me8M 8. MM8Me |
|
88 | [888] |
| |
Me, MM8 | |
88 | [888] |
| |
8. Me, MM8, 8.8 e 8. MM8Me |
|
88 | [888] |
| |
8. Me, MM8, MMM, e-MeMM 8. MeMM |
|
eeeeee | [888] |
| |
8. Me, MM8, e-MeMM, MMM 8. MeM 8. MMMM, MMM |
|
88 | [888] |
| |
8. Me, MM8, MMM 8. MM8Me |
|
88 (8:8) | [888] |
e Meee 88% eeeee eeee ee MM8Me eeee eeeeeee ee MeMM ee eeee 8. M8 = M. Meee M8 = MMM, e eeeeeee eeeeeee eeeeeee.
Mee eeeeeeeeee eeeee eeeeeeeeee ee α-eeeeeeeeee-eeeeeeeeeee eeeeeee eeee ee eeeeeeeeeeeeeeeee eeeeeeeee eeeeeee eeeeee eee eeee eeee eeeeeeee.[888,888] α,β-Meeee eeeeeee (e.e., 888),[888–888] α-eeee eeeeeee,[888] α-eeeeeee eeeeeee (e.e., 888),[888] α-eeeeeeeeeeeee[888] ee α-eeeeeeeeeeee eeeeeee,[888] eee α-eeeee eeeeeee (888 eee 888)[888–888] eeeeeee eeeeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeee eeeeeee eeeeee eeee eee ee eeeeeeeeee ee eeeeeeeee (Meeee 88). Me eeeeeeeeee ee eeeeeee (e.e., eeeeee eeeeeee) ee ee eeeee eeeeee eeeeee, eee eeeeeeee eeeee eee eeeeeee eeeeeeeeee eeeeeeeee (e.e., 888, Meeee 88).[888,888] Meeeeee ee eeeeee eeee ee eee eeeeeeeee ee α-eeee eeeeeee, eee eeeee eeee ee eee eeeeeee ee eeeeee. M eeeeeeeeeeeeee eeeee ee eee eeeeeeeee eeeeeeeeeee ee α,β-eeeee eeeeeee eee eeee eeeeeeee.[888] Mee α-eeeee eeeeeeeeeeeee ee eeeeeee eeeeeeeeeeeeee ee eee α,β-eeeee ee 888[888] eee eeeeeeeeee α-eeeee eeeeee 888 eeeeeeeee eeeeeeeee eee eeeeeeeeee ee eee α-eeeeeeee ee eee eeeeeeeee eeeeeeeee.[888]
Meeee 88 Meeeeeeeee Meeee Meeeeeeeee ee α,β-Meeee, α-Meeeeee, eee α-Meeee Meeeeee[888,888,888,888]
| Meeeeeeee | Meeeeeeeee | Meeeeee(e) | Meeee (%) | Mee |
|---|---|---|---|---|
| |
8. Me, MM8, Me8M 8. MeM, Me8M |
|
88 | [888] |
| |
8. Me, MM88. MeMM8Me 8. M8M ee M8M eeee Meeee eeeeeeeee |
|
88–88 | [888] |
| |
8. Me, eeeeeeeeeee (88 eeeee), MMM, −88°M, 88 eee8. MeMM | |
88e | [888] |
| |
8. Me, eeeeeeeeeee (8 eeeee), −88°M, 88 eee8. MeMe, 88 e | |
88 | [888] |
e eeeee/eee 8:8.
Meeeeeeeeeee Meeeeeeee
Meeeee 88-Mee-88β-(eeee-8-ee-8-ee)eeeeeeeeee-88-eeee (888):[888]
M eeee ee Me (88 ee, 8.8 eeee) ee eee MM8 (8 eM) eeeeeeeee ee e eeeeee (−88°M) eeeeeeee eeeeee eee eeeeee eeeee ee e eeee-eeeeeee eeee ee eeeee 888 (888 ee, 8.88 eeee) ee e eeeeeee ee Me8M (8 eM) eee MM8 (88 eM), eeee ee −88°M. Meeee eeeeeeee ee eeeee MM8Me, eeeeeeee ee eeeeeeeeeee ee eee MM8, M8M eee eeeee eee eee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee, eeeeeeeeeeee, eee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/Me8M 8:8) ee eeee eee eeeeeee; eeeee: 888 ee (88%); ee 888–888.8°M; [α]M −88.8 (e 8.8, MMMe8).
(8M,8eM,8M,8M,8eM)-8-Meeeeeeeeee-8,8e,8,8e-eeeeeeeeeeeeeeeeeeee-8M-eeeee-8-eee (888):[888]
Me eeeeeeeeeeee eeeeeee, eeeeeee eeeeeeeee (eeee Me) eee MM8 (88 eM) ee e eeeee-eeeeee eeeee eeeeeeee eeee e Meeee eeeeeeeee eee eeeee e eeee ee eee eeeeeeeee eeeeee 888 (888 ee, 8.88 eeee) ee eee MMM (8 eM), eeeeeeee ee eeeeeee eee Me (88 ee, 8.88 eeee) ee eeeee eeeeee. Mee eeeeeeeee eeee eeeeeee eeee eee eeeeeee eee 88 eee eee eeee eee eeeeeeee eee eeeeeeee eeee eeeee MM8Me. Meeee eeeeeeeeeee ee MM8, eee eeeeeee eee eeeee ee ee M8M (88 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eee eeeeee eeee eeeee eee eeeee (Me8MM8). Meeeeee ee eee eeeeeee eee eeeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88) eeeeeeeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 88 ee (88%); [α]M88 −88 (e 8.8, MMMe8).
References
| [207] | Meee, M.-M.; Meeee, M.-M.; Mee, M.; Mee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [208] | Mee, M.-M.; Mee, M.-M.; Meee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [209] | Mee, M.-M.; Meee, M.-M.; Mee, M.-M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
| [210] | Mee, M.-M.; Mee, M., Meeeeee, (8888), 8888. |
| [211] | Mee, M.-M.; Me, M. M.; Me, M.-M.; Meee, M.-M.; Mee, M.-M., Meeeeee, (8888), 888. |
| [212] | Mee, M.-M.; Me, M.-M.; Me, M.-M.; Meee, M.-M., Meeeeee, (8888), 8888. |
| [213] | Me, M.-M.; Meee, M.-M.; Mee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [266] | Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [299] | Meeeee, M.; Meee, M.; Meee, M.; Meeeee, M., Meeee. Meeeee., (8888) 8, 888. |
| [537] | Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [545] | Meeeee, M. M.; Meeee, M.; Meee, M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [577] | e'Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [578] | Meeee, M., Mee. Meeee. (M. M.), (8888) 88, 8. |
| [579] | Meeeee, M.; Meeeeeeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
| [580] | Meeeee, M.; Meeóe, M. M.; Mee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [581] | Meeee, M. M.; Meee, M. M. M.; Meeeee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [582] | Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [583] | Meeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [584] | Meeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [585] | Meeeee, M.; Meee, M., Mee. M. Mee. Meee., (8888), 8888. |
| [586] | Meeeeeee, M.; Mee, M.; Meee, M.; Meeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [587] | Meeeeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [588] | Meeeeeee, M.; Mee, M., M. Mee. Meee., (8888) 88, 8888. |
| [589] | Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [590] | Meeee, M.; MeMeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [591] | Meeee, M.; Meee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [592] | Meeeeeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [593] | Meeeeeee, M.; Mee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [594] | Meeee, M. M., MMM; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [595] | Meeeeeeee, M. M.; Meeeeeeeee, M., Meeeeee Mee. Meee., (8888), 888. |
| [596] | Meeeeee, M. M.; Meeeee, M. M.; Meeee, M. M., MMM, M. Mee. Meee., (8888) 88, 8888. |
| [597] | Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [598] | Meeee, M.; Meeeeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [599] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [600] | Meeeó, M. M.; Meeee, M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeee, M.; Meee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [601] | Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [602] | Meeeee, M.; Meeeeee, M.; Meee, M.; Mee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [603] | Meeeeeee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [604] | Meeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [605] | Meeeeeeeeeeee, M. M.; Meee, M. M.; Meeeeeeeeeee, M. M.; Meeeeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [606] | Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [607] | Meee, M.; Meeeee, M.; Meee, M.; Meeeeee, M. M.; Meeeeee, M.; Meeeeeee, M. M., Mee. M. Meee., (8888) 88, 888. |
| [608] | MeMeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [609] | Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [610] | Meeeee, M.; Möeeeeee, M.; Meeee, M.; Meeee, M.; Meeeee, M.; Meeeeãe, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [611] | Meeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeee, M. M., Meee. Mee. (Meeeee), (8888), 888. |
| [612] | Meeeeeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
| [613] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [614] | Meeeeee, M.; Meeeeee, M. M. M., Mee. M. Meee., (8888) 88, 888. |
| [615] | Meeeeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [616] | Meeeeeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; MeMeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [617] | Meeeeeee, M. M.; Meeeeeee, M.; Meeeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [618] | Meeeeee, M.; Meeeeeee, M.; Meee, M., Meeeeeeeeee, (8888) 88, 888. |
| [619] | Meeeee, M.; Meeeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [620] | Meee, M.-e.; Mee, M.-e., Meeeeeeee, (8888), 888. |
| [621] | Meee, M.; Meee, M.; Meeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
| [622] | Meeee, M.; Meeeeee, M.; Meeeeeeeee, M.-M.; Meeeeeeee, M.; Meee, M., Meee. Mee., (8888) 888, 8888. |
| [623] | Meeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [624] | Meeeee, M. M.; Meeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [625] | Meeee, M.; Meeeee, M.; Meeeeãe, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [626] | Meeeee, M. M.; Meeeee, M. M.; Mee, M. M.; Mee, M. M., M. Meeeeeee Meeee. Meeeeeeeee., (8888) 88, 8888. |
| [627] | Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [628] | Meeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [629] | Meeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 88. |
| [630] | Meeee, M.; Meeeeeeee, M.; Meee, M.-M.; Meeeee, M.; Meeeeee, M.; Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [631] | Meeeeeee, M.; Meeeee, M.; Meee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [632] | Meeeeeeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [633] | Meeeeeeeee, M.; Meeeeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [634] | Meeeeeeeee, M.; Meeeeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [635] | Meee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [636] | Meee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [637] | Meeeeeeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [638] | Meeeeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meee-Meeeee, M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [639] | Mee, M. M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
| [640] | Meeeeeeee, M.; Meeee, M. M.; Mee, M.-M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [641] | Meeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meee, M.; Meeeee, M.; Mee, M.; Meee, M.; Meeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
| [642] | Meeeeeee, M. M.; Meeee, M. M.; eeMeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [643] | MeMeeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [644] | Meeee, M.; MeMeeeeee, M. M.; Mee Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [645] | Meeee, M.; Meeee, M.; Mee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [646] | Meeeee-Meéeeeee, M.; Meee, M.; Meeeeee, M. M.; Meeeèee, M., Meeee. Meeeee., (8888) 88, 888. |
| [647] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
Return to Top