Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
19.5.17.1.5.1 Palladium-Catalyzed Approaches: Homogeneous Catalysis

DOI: 10.1055/sos-SD-119-00053

Rudzinski, D. M.; Leadbeater, N. E.Science of Synthesis Knowledge Updates, (20121374.

In 1-methylpyrrolidin-2-one as the solvent, a range of aryl bromides can be converted into the corresponding nitriles using palladium(II) acetate as a catalyst, sodium carbonate as a base, and potassium hexacyanoferrate(II) (0.2equiv) as the source of cyanide (Scheme 23).[‌59‌] The reactions are performed under rigorously dry and oxygen-free conditions. Catalyst loadings range from 0.005 to 0.1mol% and reactions are run for 16hours at 120140°C. Good to excellent yields of the product nitriles 23 are obtained and high turnover numbers observed. However, the yields obtained drop as catalyst loadings are increased. This is not unprecedented and similar observations are made when performing other palladium-catalyzed reactions such as Heck or Suzuki couplings.[‌65‌,‌66‌] When so-called ligandless palladium sources such as palladium(II) acetate or palladium(II) chloride are used, couplings occur best at very low catalyst loadings, thus avoiding the aggregation of catalytically inactive palladium black in the reaction mixtures over time.

Meeeee 88 Meeeeeeee(MM) Meeeeee Meeeeeeee Meeeeeeee ee Meee Meeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌]

Meeee eeeeeeeeee eeeee eeeeeeeee(MM) eeeeeee ee eeeeeeee eeee eeee eeeeeeee, eeeeeeeee ee e eeee eeeeee eee eeeeeeeee ee e eeeeeeeeeeee eeeeee.[‌88‌,‌88‌] Me eeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee ee eee eeeeeee eee ee eeeeeeee eeeeeeee ee 8.88.8eee% ee ee eeeeeeee ee eeeeeee eeeeeeee 88 ee eeee eeee 8eeeee ee 888°M (Meeeee 88). Meeeee eeeeeeeee ee eeee ee eeee eee eee eeeeeeeee eee eeeeeeeee eeeee eeeeeeee eeeeee-eeee eeeeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeeeee Meeeeeee ee Meeeeeeee(MM) Meeeeee Meeeeeeee Meeeeeeee ee Meee Meeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌]

M eeeee ee eeee eeeeeee eee eeee eeee eeeeeeee eee ee eeeeeeee eeeeeeeeeee eeeee eeeeeeeee eeeeeeeeeeeeeeee(MM) (8.8eeeee) eeeeeee eeeeeeeee eeeeeeeee eeeeeeeeee. Mee eeeeeeeee eee eeeeeeee eeeeee 88 eeeeeee, eeeeeee ee 888°M, eeee eeeee eeeee ee eee eeeeeee, eeeeee eeeeeeee ee e eeee, eee eeeeeeeeeeeeeeeeee eeeeeee ee e eeeee-eeeeeeee eeeee.[‌88‌] Meeeeee, e eeeeeeeeee eeee eeeeeeee eeeeeee (8eee%) ee eeeeeeee. Mee eeeeee eee eeee eeeee ee eee eeeeeeeeeee eeeeeeeee ee eee eeeeee eeeeeeeee eeeeeee ee eee eeeeee eee eeeeee ee eee eeeeeeee. M eeeee ee eee eeeeeee ee eeeeee eeeeeeeee ee eee eeeeeeeeee ee eeeeeeeeeee eeee eeeeeeeeeeee eeeee eeeeeeeee(MM) eeeeeee ee eee eeeeeeee eee 8-eeeeeeeeeeeeeeee-8-eee ee eee eeeeeee eee eeeee eeee eee eeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeee eee eeeeeeee ee eee ee eeeee eeeeeeee ee eeeeeeeeeee, eee eeeee eeeeeeeeee eeeee eeeee.[‌88‌] Meee eeeeeee ee e eeeee eeeee ee ee eeeeee eeeeeeeeee ee ee eeee ee eeeeeee eee eeeeeeee ee eee ee eeeeeee ee eeeeeeeeee ee eeeee eeeeeeee ee eeeee eee ee eeeeeeeeee eeeeeeeeeeee eeeeeeee. Me eeeeee e eeeee eeeeeeee ee eeeeee-8-ee ee eee eeeeeee, ee ee eeeeeeee ee eeeeeee eee eeeeeee eeeeee ee eeeeee. Meee eee eee ee e eeeeeeeeeee eeee eee eeee eeeeee ee e eeeee ee eeee eeeeeeee eee eeeeeee ee eeee eeeeeeee 88. Meeee eee eeee eeeeee (8.8eeee), eeeeeeeee(MM) eeeeeee (8.8eee%), 8-eeeeeeeeeeeeeeee-8-eee (8eM) ee eee eeeeeee, eee eee­eee-8-ee (8.8 eee%) ee ee eeeeeeee, eee eeeeeeeee eee eeeeeeee eeeee 88 eeeeeee ee 8eeeee eeee eee eeeeeee ee eeeeee ee 888°M (Meeeee 88). Mee eeeeeeeeeee ee eeeeeeee, eeeee eeeeeeeeeeee ee eee 8.8-eee eeeee. Me 8-eeeeeeeeeeeeeeee-8-eee ee eeee ee eeeeee, eee eeee eeeee e eeeeeeeeee eeeeeee ee eeeeee eeeeee, eeeeeeeeeeeeeeeee eee eeeee ee ee eeeeeeeeeee eeeeeee eeee ee eeeeeeeeeee eeeeee ee eee eeeeeee ee eee eeeeeeee.

Meeeee 88 Meeeeeeee(MM) Meeeeee Meeeeeeee Meeeeeeee ee Meee Meeeeee ee Mee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌]

Meeeeeee eeeee eeeeee eeeeeeeee eeeee eee eeeeeeeeee ee eeeee ee eeee ee eee, eeee, eee eeeee eeeeeee eeeeeee eeeeeeeeeeee, eeeeeeeee eeeee eee ee eeeeeee. Me eeeee ee eee eeee eeeeeeeee ee ee eeeeeeeee ee eee eeeeeeeeee eeeeeee. Meee eeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee 88 eee ee eeeeeeee eeee eeeee e eeeeeeee eeeeee eeeeeeeeee eeeeeeeee(MM) eeeeeee eee ee(8-eeeeeeeee)-8-eeeeeeeeeeeeee (MeeeMMeee M) ee e eeeeee (Meeeee 88).[‌88‌] Meeeeeeee eeeeeeee ee 8.888.8eee% eee eeeeeeeeee eeee e eeeeeeeee-ee-eeeeee eeeeeeeeeeeeee eeeee ee 8:8 ee eeee. Meeeee eeeeeeeee (8.8eeeee) ee eee eeeeeee eeee eee eee eeeeeeee, eee eeeeeeee eeeee eeeeee eee 88eeeee ee 888888°M. Me eeee ee eeee, eeee eeee e eeeeee ee eeeeeeeeee, eeeee eeeeeeeee eeeeeeeeeeeeeeee(MM) ee eeeeeee ee eee eee-ee-eee-eeeeee eeeeeeeeee ee eeeeeeee ee eeeee ee eeeeee eeee eeeeee ee eee eeeeeee eeeeeee.

Meeeee 88 Meeeeeeee(MM) Meeeeee/MeeeMMeee M Meeeeeeee Meeeeeeee ee Meee Meeeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌]

Me eeeeeee eeeeeeee, eeee eeeeeeeee eee ee eeeeeeee ee e eeeee/eeeeeee eee eeeee eeeeeeeee(MM) eeeeeee eee eee eeeee eeeeeeeee eeeeee MMeee.[‌88‌] Me eee eeeeeeee ee e eeee eee ee eeeeeee eee 88eeeee ee 888888°M, ee eeeeeeeee eeeee ee eeee eeeeeeeee eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee 88 eeee eeee ee eeeeeeeee eeeeeeeeeee (Meeeee 88). Meeeeeee eee eeeeee ee MM-eeee, ee eeeeeeeeeeeeeeee eeeeeeee, eeeeee eeeeeee eeeeeeee.[‌88‌] Meee eeeee eee eeeeeeeee eeee (8eee%) eee eee eeeeeeeee (8eee%) eeeee eeeeeeeee eee ee eeeeeeeee ee eeeee ee e eeeee/eeee-eeeee eeeeeee eee ee eee eeeeeee, eeee eeeeeeeee eeeeeeeee ee e eeee eee eeeeeee eee eeeeeee ee 88°M eee 88eeeee.

Meeeee 88 Meeeeeeee(MM) Meeeeee/MMeee Meeeeeeee Meeeeeeee ee Meee Meeeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌]

Me eeeeee ee eeeeeeeee(MM) eeeeeeeeeeeeeeee ee ee eeeeeeee ee eeeeeee eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeee eeeeeeeeee ee eeeeeee.[‌88‌] Meeee eeeeeeeeee eee eeeeeeeeeee eeeeeeeee ee eeeeee, eee eee eeee eeee eee eeeeee eee eeeeeee eeeeeeeeeeeeeee ee eee eeee ee ee eeeeeeeee ee ee eeeeeeeeee eeeeeeeeee eeeee. Meeeeee, ee eee eeeeeeee eeeeee eee ee eeee eee eee eeeee eeeee ee eeeeeeeeee. Meeeeee, eeeeeeeee eeee ee ee eeeeeeeee eeeeeeeeeee ee e eeee-ee-eeee eeeee.

Meeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeee ee eeeeeeeee ee eeeeeeeee eeeeeeeee eeeee eeeeeeeee eeeeeeeeeeeeeeee(MM). Me eeeeeeeeeeeeeeeee ee eee eeeeeee eee eeeee eeeeeeeee eeeeeee, e eeeee ee eeee eeeeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee ee 888 eeeeeee eeeee eeeeeeee eeeeeeee eeeeeeeeeeeee eeeeeeeee.[‌88‌,‌88‌] Meeee eeeeeee eee eeee eeeeeeeeee ee eeee eeeeeeee eee eeeeeee eee eee eeeeeeee eeeeee ee ee eeeeeee eeee eeeee eee eeeeeeeeeee eeeeeeeee eeee eee ee eeeeee eeeeeeeee eeeee ee eeee eeeee. Meeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeee eeee eeee eeee eee eeeeeeeee ee eeee eeeeeeeee (Meeeee 88).[‌88‌] Meeeeeeee eee eeeeeeee eeeeee 8888eeeee ee eeeeeee ee 888°M ee 8-eeeeeeeeeeeeeeee-8-eee ee eee eeeeeee. Mee eeeeeee eeeeeeee eeeeeee ee 8eee%.

Meeeee 88 Meeeeeeee ee Meee Meeeeeeee Meeee e Meeeeeeeeeeeeee Meeeeeeeeeeeeee Meeeeee eee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌]

Meee eeeeeeeeeeeeeeeeeeeeeeeeee, eeeeeeeeeeeeeeeee, 8-eeeeeeeeeeeeeeeee, eee eeeeeeeeeeeeeeeee eee eeee ee eeee ee eeeeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeee(MM) ee eeee eeeeeeee 8888 (Meeeee 88). Mee eeee eeeee ee eeeeeee eeee ee eeeeeeeeeeee eeeeeeeee eeeee eeeee eeeeeeeeeee eeeeee eeeeeeeeeeeee ee eeeeeeeeeeee ee eeee eeeeeee. Meeeeeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeee eeeee e eeeeeee­ee(MM) eeeeeee/8,8-eee(eeeeeeeeeeeeeeeee)eeeeeeeee eeeeeeee eeeeee [eeeeeeeee (8eee%), 8:8 eeeeeeeee/8,8-eee(eeeeeeeeeeeeeeeee)eeeeeeeee eeeee].[‌88‌] Meeeee eeeeeeeee ee eeee ee eeee eee eee eeeeeeeee eee eeeeeeeee ee 888°M eee 88eeeee ee eeeeeeeeeeeeeeeee eeeee eeeeeeeee eee eeeee-eeee eeeeeeeeee. Me eee eeee ee 8-eeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee, eee eeeeeeeeee eee ee eeeeeeeee ee eeeee/eeeeeee ee e eeeeeee eeeee e eeeeeeee eeeeee eeeeeeee ee eeeeeeeee(MM) eeeeeee (88eee%) eee eeeeeeeeee MMeee, e eeeee-eeeeeee eeeeeeee ee MMeee, ee eee eeeeee (8eee%).[‌88‌] Meeeeeeee eeeeeeeee eeeeee ee eee eeee eee eee eeeeeeeee eee eeeeeeee eeeee eeeeeee ee 888888°M eee 88eeeee. Meee eeeeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeeeeee eee ee eeeeeeee eeeee eeeeeeeee(MM) eeeeeee ee eeeeeeeeeee eeee MM-eeee.[‌88‌] Meeee eee eeeeeeeee eeee (8eee%) eee eee eeeeeeeee (8eee%), eee eeeeeeeee eee eeeeeeeee ee eeeee ee e eeeee/eeee-eeeee eeeeeee eee ee eee eeeeeee ee 88°M eee 88eeeee eeeee eeeeeeeee eeeeeeeee ee e eeee.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meee Meeeeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MM)[‌88‌,‌88‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
8-Mee 88 [‌88‌]
8-Mee 88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]

M Me8 Meeeee Meeee (%) Mee
MMe 8-MeMM8M8 MMeee-MM8Me 88 [‌88‌]
MMe 8-MeMM8M8 MMeee-MM8Me 88 [‌88‌]
MMe Me MMeee-MM8Me 88 [‌88‌]
MMe 8-Mee MMeee-MM8Me 88 [‌88‌]
MMe 8-Mee MMeee-MM8Me 88 [‌88‌]
MMe 8-Mee MMeee-MM8Me 88 [‌88‌]
MMe 8-eeeeeeee MMeee 88 [‌88‌]
MMe 8-eeeeeeee MMeee 88 [‌88‌]
MMM8Me 8-MeMM8M8 MMeee-MM8Me 88 [‌88‌]
MMM8Me 8-MeMM8M8 MMeee-MM8Me 88 [‌88‌]
MMM8Me Me MMeee-MM8Me 88 [‌88‌]
MMM8Me 8-Mee MMeee-MM8Me 88 [‌88‌]
MMM8Me 8-Mee MMeee-MM8Me 88 [‌88‌]
MMM8Me 8-eeeeeeee MMeee 88 [‌88‌]
MMM8Me 8-eeeeeeee MMeee 88 [‌88‌]

M Me8 Meeee (%) Mee
MMe 8-e-MeM8M8 88 [‌88‌]
MMe 8-MeM8M8 88 [‌88‌]
MMe 8-MeMM8M8 88 [‌88‌]
MMe 8-MMM8M8 88 [‌88‌]
MMe 8-MeM8M8 88 [‌88‌]
MMe 8-e-MeM8M8 88 [‌88‌]
MMe 8-MeM8MM8M8 88 [‌88‌]
MMe 8-MeM8M8 88 [‌88‌]
MMe 8-M8MM8M8 88 [‌88‌]
MMe 8-MeM-8-MeM8M8 88 [‌88‌]
MMe 8,8-Me8M8M8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee ee 8-Meeeeeeeeeeeeeee-8-eee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

M8Me(MM)88M8M (888ee, 8.8eeee) eee eeeee Me8MM8 (888ee, 8.8eeee) eeee eeeeee ee e eeee eeeeee, eeeeee ee e eeeeeeee eeee eee eeeee ee eeeee (ee. 8 eeee, ee 88°M eeeeeeeee). Mee eeeeee eeee eeeeeee eeee eeeee eee ee eeeee 8eee, eee eeee eee eeee eeeeeee (8eeee) eee e eeeee eeee ee Me(MMe)8 (8.8888.8eee%) ee MMM (8eM) eeee eeeee. Mee eeee eee eeeeee eee eee eeeeeee eee eeeeeee eee 88e ee 888°M. Meeee eeeeeee ee ee, eee eeeeeeeeee eee eeeeeee eeee MM8Me8 (8eM). Mee eeeeeeee ee eee eeee eeee eeeeee eeee M8M, eee eee eeeeeeee eeee eeeeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee); eeeee: 8888%.

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee ee Meeeeeeeeeeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

M8Me(MM)88M8M (888ee, 8.88eeee), eeeee Me8MM8 (888ee, 8eeee), eee eeee eeeeeee (8eeee), Me(MMe)8 (8.88.8eee%), eee MMM (88eM) eeee eeeee ee e 88-eM eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee. Mee eeeee eee eeeeeeeee eee eeeeee eeee M8 (8 ×) eee eee eeeeeee eee eeeeeee eee 88e ee 888°M. Meeee eeeeeee ee ee, eee eeeeeeeee eeeeeee eee eeeeeee eeee MeMMe (88eM). Mee eeeeeeeee eeeeee eee eeeeeeee eee eee eeeeeeee eee eeeeee eeee M8M (8 × 88eM), eee 8% MM8MM (88eM). Mee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee ee eeeee ee eeeeee eee eeeeeee eeeeeee; eeeee: 8888%.

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee ee e Meeee Meeee Meeee Meeeeeeee(MM) Meeeeee eeee Meeeee-8-ee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

Me8MM8 (888e, 8.8eee), Me(MMe)8 (8.8e, 8.88eee), eee eee eeee eeeeeee (8.8eee) eeee eeeee eeee MMM (8.8M), eMeMM (8.8 eee%), eee M8M (8.8 eee%) ee e eeeeeeee eeeeeeee eeeeee. Meeee eeeeeee ee 888°M, M8Me(MM)88M8M (888e, 8.88eee) eee eeeee. Mee eeeeee eee eeee eeeeee eee eee eeeeeeee eeeeeeee eee 88eee ee 8e ee 888°M eeeee ee eeeeeeee eeeeeee. Meeee eeeeeee ee ee, eee eeeeeeeee eeeeeee eee eeeeeeee eee eee eeeeee eeee eee eeeeee eeee MMM (888eM). Meeeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeee; eeeee: 8888%.

8-Meeeeeeeeeeeeeeeee (88, Me8=8-Mee); Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee/MeeeMMeee M:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

Mee M8Me(MM)8 (888ee, 8.8eeee), 8-eeeeeeeeeeeee (888ee, 8.8eeee), eee Me8MM8 (88.8ee, 8.8eeee) eeee eeeeee ee e eeeeeeee eeee eeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee. M eeee ee Me(MMe)8 (8.88ee, 8.88eeee) eee MeeeMMeee M (88.88ee, 8.88eeee) ee MMM (8eM) eee eeee eeeee. Mee eeee eee eeeeee eee eee eeeeeee eee eeeeeee eee 88e ee 888°M. Meeee eeeeeee ee ee, eee eeeeeeeeee eee eeeeeee eeee MM8Me8 (8eM). Mee eeeeeeee ee eee eeee eeee eeeeee eeee M8M, eee eee eeeeeeee eeee eeeeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee); eeeee: 88%.

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee/MMeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

Me(MMe)8 (8.8ee, 8.888eeee), MMeee (88.8ee, 8.88eeee), M8MM8 (88ee, 8.88eeee), eee M8Me(MM)88M8M (888ee, 8.88eeee) eeee eeeee ee e eeeeeeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee. Mee eeee eee eeeeeeeee eee eeeeeee eeee eeeee (8 ×), eee eeee eee eeee eeeeeeee (8eeee), ee eeeeee, eee eeeeeee/M8M (8:8; 8eM) eeee eeeeeeeeee eee eeeeeee (eeee eeeeeeeee eeee eee eeeeee ee ee eeee eeeee eeee eee eeeeeeeee eeeeeeee eee eee eeeeee). Mee eeee eee eeeeee eee eee eeeeeee eee eeeeeee eee 88e ee 888888°M. Meeee eeeeeee ee ee, eee eeeeeeeeee eeee eee eeeeeeee eee eeeeeee eeee Me8M (88eM) eee eee eeeeeeee eeee eeeeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee; eeeee: 88888% [MM, eeeeeeeeee (888μM) ee ee eeeeeeee eeeeeeee].

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee/8,8-Mee(eeeeeeeeeeeeeeeee)eeeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

Me(MMe)8 (88.8ee, 8.88eeee), eeee (88.8ee, 8.8eeee), Me8MM8 (888ee, 8.8eeee), eee eeee eeeeeeeeeeeeeeeeeeeeeeeee (8.8eeee), eee M8Me(MM)8 (88ee, 8.8eeee), eee MMM (8eM) eeee eeeee ee e eeeeeeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee. Mee eeee eee eeeeeee eeee M8 eee eeeeee, eee eee eeeeeee eee eeeeeee eee 88e ee 888°M. Meeee eeeeeee ee ee, eee eeeeeeeeee eeee eee eeeeee eee eeeeeee eeee MeMMe (88eM) eee eeeeeeee. Mee eeeeeeee eee eeeeee eeee M8M (8 × 88eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee ee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee); eeeee: 8888%.

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meee 8-Meeeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeee eee Meeeeeeee(MM) Meeeeee/MMeee-MM8Me:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

Me(MMe)8 (8.8ee, 8.888eeee), MMeee-MM8Me (88.8ee, 8.888eeee), M8MM8 (88.8ee, 8.88eeee), eee M8Me(MM)88M8M (888ee, 8.88eeee) eeee eeeee ee e eeeeeeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee. Mee eeee eee eeeeeeeee eee eeeeeee eeee eeeee (8 ×) eee eee eeee 8-eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeee (8eeee), ee eeeeee, eee eeeeeee/M8M (8:8; 8eM) eeee eeeee (eeee 8-eeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee eeee eee eeeeee ee ee eeee eeeee eeee eee eeeeeeeee eeeeeeee eee eee eeeeee). Mee eeee eee eeeeee eee eee eeeeeee eee eeeeeee eee 88e ee 888°M. Meeee eeeeeee ee ee, eee eeeeeeeeee eeee eee eeeeee eee eeeeeee eeee Me8M (88eM) eee eee eeeeeeee eeeeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee; eeeee: 8888% [MM; eeeeeeeeee (888μM) ee ee eeeeeeee eeeeeeee].

Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee(MM) Meeeeee/MM-eeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eee eeeeee e eeeeeeeeee eeeeee.

Me(MMe)8 (8.8ee, 8.88eeee) eee MM-eeee (88.8ee, 8.88eeee) eeee eeeeee ee e Meeeeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee. Mee eeee eee eeeeeeeee eee eeeeee eeee M8 (8 ×) eee eeee eeeeeee eeeeeeeee eee MM8Me8 (8.8eM) eee Me8M (8.8eM) eeee eeeee. Meeee eeeeeeee, eee eeee eee eeeeee eeeee eee eeeeeee eeeeeeeee ee eee Meeeeee eeee eeee. Mee eeeeeee eee eeeeeee eeeee eeeeee. Mee eeee eeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeeeee (8.8eeee), M8MM8 (88ee, 8.888eeee), eee M8Me(MM)88M8M (888ee, 8.8eeee) eeee eeeeeee eeeeeeeeeeee ee eee eeee, eeeeeeee ee eeeeeeeeee/eeee eeeeee eeee M8 (8 ×). M8M (8.8eM) eee eeeee, eee eeee eee eeeeee eee eee eeeeeeee eeee eeeeee ee 88°M eee 88e. Meeee eeeeeee ee ee, eee eeeeeeeee eeeeeee eee eeeeeee eeee MeMMe (88eM). Mee eeeeeee eeeee eee eeeeeee eee eee eeeeeee eeeee eeeeeeeee eeee eeeeeee eeeeeeee ee MeMMe (8 × 88eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee ee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee ee Me8M/eeeeeee); eeeee: 8888%.

References


Cookie-Einstellungen