0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. Method 1: Oxidation of 1,2-Dialkylhydrazines

DOI: 10.1055/sos-SD-041-00470

Kempa, S.; Wallach, L.; Rück-Braun, K.Science of Synthesis, (201041469.

The oxidation of 1,2-dialkylhydrazines has been known since the end of the 19th century, when the synthesis of 2,2-azobisisobutyronitrile and derivatives from the corresponding hydrazines using bromine water was reported.[‌3‌] These reactions are generally carried out in the presence of hydrochloric acid by adding bromine water to a cooled solution of the starting material dissolved in ethanol. The mechanism is assumed to involve bromination at nitrogen followed by elimination.[‌67‌] Comparable but anhydrous reaction conditions, using bromine as the oxidizing agent and benzene or tetrahydrofuran as the solvent, to give dialkyldiazenes 22 in good yields have also been employed (Scheme 15).[‌68‌] Another common oxidant which has been successfully applied in the oxidation of 1,2-dialkylhydrazines to give dialkyldiazenes 22 is mercury(II) oxide.[‌69‌‌72‌] These oxidation reactions are generally carried out in water[‌69‌] or anhydrous diethyl ether,[‌72‌,‌73‌] affording yields of 5196%. Oxidation reactions with benzeneseleninic anhydride or benzeneseleninic acid in tetrahydrofuran or deuterated chloroform also furnish diazenes in very good yields at room temperature. An advantage of these oxidants is the short reaction times required.[‌74‌,‌75‌] It is also possible to oxidize hydrazines with elemental oxygen, hydrogen peroxide, or even commercial bleach.[‌35‌,‌73‌,‌76‌] In an interesting variation, the hydrazine precursors are formed from 2 equivalents of an isocyanate with hydrogen peroxide as oxidant.[‌77‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeee[‌88‌,‌88‌‌88‌,‌88‌‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) Mee
MM8MM MM8MM Me8, eeeeeee, MeMM/MMe, 88°M, 8e 88 [‌88‌]
M(MMe)8MM M(MMe)8MM Me8, MMM, MeMM, 88 ee 8°M, 8e 88e [‌88‌]
Me Me MeM, M8M 8888 [‌88‌]
eMe eMe MeM 88e [‌88‌]
MeM, eee Me8M, eeeeee, 88e 88 [‌88‌]
MM(Me)e-Me MM(Me)e-Me MeM, eee Me8M, 88e 88 [‌88‌]
e-Me MM8MM=MM8 MeM, Me8M, eeeee Me8MM8, ee, 8e 88 [‌88‌]
eMe eMe (MeMeM)8M (8eeeee), MMM, ee, 8eee 88 [‌88‌]
eMe eMe (MeMeM)8M (8.8eeeee), MMMe8, ee, 88eee eeeeee [‌88‌]
eMe eMe MeMeM8M (8.8eeeee), MMMe8, ee 88e [‌88‌]
eMe eMe MeMeM8M (8eeeee), MMMe8, ee eeeeee [‌88‌]
MM8MMe=MM8 MM8MMe=MM8 M8, eeeeeeeeeee, 8°M, 8.8e 88 [‌88‌]
MM(Me)e-Me MM(Me)e-Me M8, Me8M, 88e 88 [‌88‌]
eMe eMe M8M8, eee. MeMMM8 e [‌88‌]
e-Me MMe8MM eeeeeeeeee eeeeee (8.88% MeMMe), 8°M ee ee >88 [‌88‌]

e Meeee eeeeeee.

e Meeee (M/M) 88:8; ee eeeee eeeee eeeee; M-eeeeee eee eeeeeeee ee eeeeeeeeeeee ee eeeee-eeeee eeeeeeeeee.

e Meeeeeeeee, eeeeeeeeee ee MMM.

e Meeee eee eeeeeeee.

Mee eeeeeeeee ee eee eeeeeeeee eeee eeeeee M-eeeeeeeeeeeeeee (M)-88 ee eeeeeeee ee eeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeee(MM) eeeee.[‌88‌,‌88‌,‌88‌] Mee eeeeeeee eee ee eeeeeeeee eeee eeee eeeeeeeeee (Meeeee M) ee eeeee eeeeeeeee eeee eeeeeeeeeeeeee [eeeeeeee (Meeeee M) ee eeeeeeee (Meeeee M)]. Meee eeeeeeee eeee eee eeeeeeeeee, eee eeeeeeeeee ee eee M-eeeeeee (M)-88 eeeeee eeeeeeeee ee eee eeee ee eee eeeee eeeeee eeeeeeeee. Mee eeeeeeeeee eeee eeeee eeeee eeeeee, eee eeeeee eee eee eee eee eeeeeeee ee eeee ee eeee eee eeeee eeeeeeeeee. Meee ee eee M-eeeeeeee (M)-88 eeee eeeee eeeee eeeeee eee eeeeeeeeee ee eeeeeeeeeeeee eeeeeeeee (Meeeee 88). Mee eeeeeeeeeeee ee eeee eeeeee ee eee eeee eee eee eeeeeeeeeee ee eee eeeeeeeeeeeeee eeeeeeeee.

Meeeee 88 Meeeeeeee Meeeeeeee ee Meeeeeeeee eee MeeeeMeeeeeeee Meeeeeeee eeee Meeeeeeee(MM) Meeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeee Meeee (%) Mee
Me Me M 88 (±8) [‌88‌]
Me Me M 88 (±888) [‌88‌]
Me Me M 88 (±8) [‌88‌]
Me Me M 88 (±888) [‌88‌]
Me eMe M 88 (±8)e [‌88‌]
Me eMe M 88 [‌88‌]
Me eMe M 88 (±888) [‌88‌]
Me Me M 88 (±8) [‌88‌]
Me Me M 88 (±888) [‌88‌]
Me Me M 888 (±888) [‌88‌]
Me eMe M 88 (±8) [‌88‌]
Me eMe M 88 (±888) [‌88‌]
eMe eMe M 8 [‌88‌]
eMe eMe M 8 [‌88‌]
eMe eMe M 88 [‌88‌]

eMeeeee M: eeee eeeeeeeee eeee; Meeeee M: eeeeeeee eeeeeeee eee eeeeeeee eeeeeeeee ee M(MM)8; Meeeee M: eeeeeeee eeeeeeee eee eeeeeeee eeeeeeeee ee Me(MM)8.

e Meeeeeee eeeee: 88%.

Meeeee 88 eeee eeeeeeeeee eee eeeeeee ee eeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee.[‌88‌] Me eeeee e eeeeee ee eee eeeeeeeeeee ee M- eee M-eeeeeeeeeeee eeeeeeeee, eeeee eeeeee ee eee eeee ee eee eeeee eeeeeeee.

Meeeee 88 M/M Meeeee ee MeeeeMeeeeee Meeeeeeee Meeeeeee ee Meeeeeeee Meeeeeeee ee Meeee Meeeeeeee Meeeeeeeee[‌88‌]

Meeeeeeeeee 88

M M8 M8 Meeeeeeeee Meeeee (%) ee M-Meeeeee Meeeee (%) ee M-Meeeeee Mee
M Me Me MeM8 (88eeeee), 88°M, 88e e e [‌88‌]
M Me Me MeM8 (8eeeee), 8°M, 88e 88 88 [‌88‌]
Me Me Me MeM8 (8eeeee), 88°M, 8e 8 88 [‌88‌]
M Me eMe MeM8 (88eeeee), 8°M, 88e 88 88 [‌88‌]
Me Me eMe MeM8 (88eeeee), 88°M, 88e 88 88 [‌88‌]
M Me eMe MeM8 (88eeeee), 88°M, 88e 88 8.8 [‌88‌]

e Meeeeeee eeeee ee eeeeeeeeeeee eeeeeeeee.

e Mee eeeeeeee. MMM eeeee eeeee eeeeeee ee M- eee M-eeeeeee eeeeeeeee.

Mee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee 88 eeee eeeeeee ee M-eeeeeeeeeeeeeeee[‌88‌] ee eee eeeeeeee ee eeeeeeee eee eeee eeeeeeeeee eeeeeee. Meeee eeeeeeeee eee eeeee eeeeeee eee ee eeeeeeeeeeeeeee, eeeeeeeeeeeeeee, ee eeeeeee ee 8°M ee ee eeee eeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeee 88 ee eeee eeeeee (Meeeee 88).[‌88‌,‌88‌‌88‌,‌88‌,‌88‌‌88‌]

Meeeee 88 Meeeeeeee Meeeeeeee ee Meeeeee Meeeeeeee-8,8-eeeeeeeeeeeeee eeee Meeeeee ee M-Meeeeeeeeeeeeeee[‌88‌,‌88‌‌88‌,‌88‌,‌88‌‌88‌]

Meeeeeeeeee 88

M8 Meeeeeeeee Meeee (%) Mee
(MM8)8(MM8)8MM8 MMM, eeeeeeee 88e [‌88‌,‌88‌]
(MM8)8(MM8)8MM8 Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8°M ee ee, 8e eeeee [‌88‌,‌88‌]
MMM (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 88°M, 8.88e 88 [‌88‌,‌88‌]
MMM (8.8eeeee), eeeeeeee (8.8eeeee), MMM, 888°M, 88e 88 [‌88‌]
(MM8)8MMe MMM (8.8eeeee), eeeeeeee (8.8eeeee), eeeeeee, ee, 8e 88e [‌88‌]
e-Me MMM (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8.88e 88e [‌88‌]
e-Me MMM (8.88eeeee), eeeeeeee (8.8eeeee), MM8Me8 ee, 8.88e 8888 [‌88‌]
8-MeM8M8MM8 MMM (8.88eeeee), eeeeeeee (8.88eeeee), eeeeeee, ee, 8.88e 88e [‌88‌]
MM8MMe8 Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8°M ee ee, 8.88e 88e [‌88‌]
Me Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8°M ee ee, 8.88e 88 [‌88‌]
Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8°M ee ee, 8e 88 [‌88‌]
(MM8)8MM(MM8)8 Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MeMM8, ee, 8e eeeee [‌88‌]

e Meeeeeeeeee eeeeeeee eeeeeeeee eeeee eeeeee: MeM8 (8%) eee Me(MMe)8 (88%).

eMeeeeeeeeeee, eeeee ee eeeeeeee eee eee eeeeeeeeeee ee, eee eeeeeee, eeeeeee eee eeeeeeeeeee eeeeeeeeeeeeeeeee, eee ee eeeeeee.

e Meeeeeeeeee ee eee 88M-eeeeeee eeeeeee.

e Meeeeeee ee ee, ee eeeeeeee ee eeeeeee eee eeeeeeeeeee eeeeeeeeeeeeeeeee.

e Meeeeeee eeee 88% eeee eeeeeeeee. Meeeeee eeeeee eee eeee eeeeee ee eee eeeeeee.

Meeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee eeee eeeeeee ee M-eeeeeeeeeeeeeeee eee eeeee ee Meeeee 88.

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeee Meeeeeeeeee Meeeeeeeeeeeeeeeeeeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) Mee
(MM8)8(MM8)8MM8 e-Me Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8°M ee ee, 8e 88 [‌88‌]
Me e-Me MMM, eeeeeeee, MM8Me8 88 [‌88‌]
Me MMM, eeeeeeee, 8°M, 8.8e 88 [‌88‌]

Meeeeee eeeee eeeeeeeee eeeeeee eee eeeeeee eeeeeeeeeeeeeeeeeeeeeee eee eeeeeeeee ee eee eeeeeeeeee (Meeee 8). Me eee eeee ee eee eeeeeeeee ee eee[(8M,8M,8M)-8-eeeeeeeee-8-eeeeeeeeeeeeeeee] eeeeeee-8,8-eeeeeeeeeeeee (eeeee 8), eeeeeeeee eeee [eee(eeeeeeeeeeeeeeee)eeee]eeeeeee ee eeeeeeeeeeeeeee eeeeeee eeeeee eeeeee eeee eee eeeeeeeee eeee M-eeeeeeeeeeeeeeee ee eeeeee eeeeee eeee (eeeee 8).[‌88‌] Meeeee 8,8-eeeeeeeeeeeeee eeeeeeeeeee eee ee eeeeeeee ee eeeeeeeee eeee eeeeee(M) eeeeeeeee ee Meeeee (eeeee 8);[‌88‌,‌88‌] eeeee eeeeeeeee eee eeeeeeee ee eeeeeee, eee eeeeeeeeeeee eeee eeee eeeeee. Mee eeeeeeeee ee eeeeeeeeeeeee ee eeee ee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeeeee eeeeeeeee eee eeee eeee eeeeeeee (eeeeeee 8 eee 8).[‌88‌,‌88‌] Meeeeee ee eeee eeeeee ee eee eeeeeeeee eeee eeeeeeee eeeeeee. Meee eee ee eeeeee eeee e eeeeeee ee eee eeeeeeeee eeeeeeeee 88 eee eeeeeeeee eeeeee eeeeeee ee eeeeeeeeeeeeeee ee 8°M (eeeee 8).[‌88‌] M eeeeeeeee ee eeee eeeeee ee eee eee ee eeee(eeeeeeee eeeeee) ee eeeeeeeee eee eeeeeeee eeeeeee (eeeeeee 8 eee 8);[‌88‌] eeee eeeeeeee eee eee eeeeeeeee ee eeeee eeee eeeeeeeeeeeeeee eeeeeeee eeeeeee eee eeeeeee eeeeeeeee ee eee eeeeeeee ee eeee eeeeeeee eee eee eeee(eeeeeeee eeeeee) eee ee eeeeeeee. Me eeeeeeeee eeee eeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeee, eeeeeeeeeeeeeeee eeeeeeeeeee 88 eee eeeeeeee ee eeee eeeeee. Meeeeee eeeeeeeeeeeeeeeeeeeeeee 88 eeee eeee eeee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeee 88 ee (eeeeeeeeeeeee)eeeeeee[‌88‌‌888‌] (eeeeeee 8888) ee eeeeeeee[‌888‌] (eeeee 88).

Meeee 8 Meeeee ee Meeeeeeee Meeeeee eee Meeeeee Meeeeeeeeeeeeeeeeeeeeee[‌88‌‌888‌]

Meeee M8 M8 Meeeeeeeee Meeee (%) Mee
8 MeM(MMMMM8)8 (8.8eeeee), MM8Me8, ee, 88e 88 [‌88‌]
8 eeeeee 88% MMM8, 88% MMM8, 88 ee 8°M, 8.8e 88e [‌88‌]
8 MM8MMe8 MM8MMe8 eeeeee MMM8 (8eeeee), MM8Me8, 8°M ee ee, 8e, eeee ee, 8e 88 [‌888‌]
8 Me Me Me8MM8 ee Meeeee (8eeeee), eeeeee, 8eee 88 [‌88‌,‌88‌]
8 MM8MMe8 MM8MMe8 M8M8 88 [‌88‌]
8 MM8MMe8 MM8MM8MMM M8M8, MM8Me8, 8°M ee ee, eeeeeeeee 88e [‌88‌]
8 MM8MMe8 MM8MMe8 MM8, eeeee Me8MM8, MM8Me8, <8°M, 8e, eeee ee, 88e 88 [‌88‌]
8 Me Me MMM/MM8e (8eeeee), 88°M, 88e 88 [‌88‌]
8 MM8MMe8 MM8MMe8 MMM/MM8e (8eeeee), 88°M, 88e 88 [‌88‌]
88 Me Me Me8, M8M, eeeeeee, <88°M 88 [‌888‌]
88 Me Me MeM(MMe)8 (8.8eeeee), MM8Me8, ee, 8.88e 88e [‌88‌,‌888‌]
88 MeM(MMe)8, MM8Me8 88 [‌888‌]
88 Me MeM(MMe)8, MM8Me8 88 [‌888‌]
88 Me Me eeeeeeeeeee eeeeeeeeeee-eeeeeeeee MeM(MMe)8 (8.8eeeee), MMM, ee, 88e 88 [‌888‌]

e Meeeeee eeeeee eeeeeee eeeeee.

e Meeeeee ee eeee eee eee eeeeeeeee ee eeeeee.

e MM8 eeeeeeee ee eeee(eeeeeeee eeeeee).

e Meee eeeeee eeeeeeee eeeeee eeeeeeee eeeeeeeeee, eeeeeeeeeeee ee eeeeeeeeeeee.

Me eeeeeeeeeee eeeeeeeeeee ee M-eeeeeeeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeee-eeeee eeeeeeeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeeeeee eeeeeeeeeee eeeee eeeee ee Meeeee 88. Mee eeeeeeee eeee ee eeeeeee eeee 88% eeeeeeeeee.[‌88‌] Meeee eeeeeee-eeeeeeeee eeeee eeeeeeeeeeeeeeee eeeeee eee eeee ee eeeeeee Meeeeeeee eeeeeeeee eee eee ee eeeeeeee ee eeeee eeeeeeeee eeeeee ee eeeeeee: eeeee (8eee%), eeeeeeeeeeee (88eee%), eee eeeee (88eee%) eeeeeee. Mee eeeeeeeeee eee eeee eeeeeee eeeeeee eee eeee eeeeeeee eee eeeee, eee eeee eeeeeeeeeee (eee eeeeeeeee) eeee eeeeeeeeee eeeeeeeee.

Meeeee 88 Meeeeeeee ee Meeeee Meeeeeeeeeeeeeee Meeeeeeeeee Meeee[‌88‌]

Mee eeeeeeeeeeeee eee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeeeee 88 eeeee ee Meeeee 88 eee eeeeeeeeee ee eeee eeeeee eeee eeeeeeeeee 88 eee eeeeeeee eeeeeeee eeeeeeeee eeee eeeeeee ee M-eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee.

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee eee Meeeeeeeeeeeeee Meeeeeeeeee Meeeeeeeeeeeeeeeee Meeeeeeeeee[‌88‌,‌88‌,‌888‌‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) Mee
MMMe MMe MMM (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee >88 [‌888‌]
8-M8MM8M8MM MMe MMM (8.88eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee, 88eee 88 [‌88‌]
MM(MM8)8Me Me-Me MMM (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee, 88eee 88 [‌888‌]
MM(MM8)8Me MMe MMM (8.8eeeee), eeeeeeee (8.88eeeee), MM8Me8, ee, 88eee 88 [‌888‌]
MMMe MMe MMM (8.88eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee, 88eee 88 [‌888‌]
8-MeMM8M8MM MMe MMM (8.88eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee, 88eee 88 [‌888‌]
8-MM8M8MM MMe MMM (8.88eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee, 88eee 88 [‌888‌]
8-MeeMM MMe MMM (8.88eeeee), eeeeeeee (8.8eeeee), MM8Me8, ee, 88eee 88 [‌888‌]
MM(MM8)8Me MMM (8.8eeeee), eeeeeeee (8.88eeeee), MM8Me8, ee, eeeeeeeee 88 [‌888‌]
MM(MM8)8Me MMM (8.88eeeee), eeeeeeee (8.88eeeee), MM8Me8, ee, 8e 88 [‌888‌]
MM(MM8)8Me MMM (8.88eeeee), eeeeeeee (8.88eeeee), MM8Me8, ee, 8e eeeee [‌888‌]
Me8 (8.8eeeee), eeeeeeee (8.8eeeee), MM8Me8, 8°M ee ee, 8888eee 88 [‌88‌]

Mee eeeeeeeeee ee eeeeeeeee-8,8-eeeeeeeeeeeee ee eeeeeee-8,8-eeeeeeeeeeeee (88, M8=M8=MM8) ee eeeeeeee eeee eeeeeeee eeeeeee ee eeeeeee eeeeee eeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeee(MM) eeeeeee eee eeee eeeeeeee (Meeeee 88).[‌888‌] Meeeeee eeeeeeeeee eeee eeee eeeeeee ee eeeeeee 88M-eeeeeee eeeeeee-8,8-eeeeeeeeeeeeee ee eeeeeeeeee eeeeee.[‌888‌] Mee eeeeeeeee ee 8,8-eeeeeeeeeeeeeee (88, M8=M8=Me) ee eeeeeeeeeeee eeee eeeeeeee eeeeeeee ee eee eee ee e eeeeeeee eeeeee eeeeeeeeee ee eeeeeeee(MMM) eeeeeeee eee eeeeeeee eeeeeee.[‌888‌] Meee eeeeeeeee eeeeeeee ee eeee eeeeeeeee eee eeeee eeeeee eeeeee ee eeeeeeeeee ee eee eee ee eeeeeeee eeeeeeeeeeee ee eeeeeeee. Meee eeeee eeeeeeee(MMM) eeeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeeee eeeeeee ee eeeeeeee eeeeeee, ee eeeeeeeee eeeeeeee eee eeeeeeee.

Meeeee 88 Meeeeeeee Meeeeeeee ee eee Meeeeeee ee Meeeee(MM) Meeeeee, Meeeeeee(MMM) Meeeeeee, ee Meeeeeee Meeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) Mee
MM8 MM8 Me(MMe)8 (8.88eeeee), MM8MM8 (8.88eeeee), eeeeeee MeMM, 888°M, 88eee 88 [‌888‌]
MM8 MM8 Me(MMe)8 (8.88eeeee), MM8MM8 (8.8eeeee), eeeeeee MeMM, 888°M, 88eee 88e [‌888‌]
Me Me MeMe8 (8.888eeeee), MMe (8.888eeeee), ee M8M8 (8.8eeeee), MeMM/MMe/MeMM, ee 88 [‌888‌]
Me Me MM8MM8 (8.888eeeee), ee M8M8 (8.8eeeee), MMe/MeMM, ee, 8eee 88 [‌888‌]

e 88M-Meeeeee eeeeeee.

M eeeee eeeee ee eeeeee eeeeeeeeeeeeeeeeeeeeeeee 88 eee eeeeeeeeee ee eeeeeeeee eeeeeeeee eeee e 88% eeeeee ee eeee(MM) eeeeeee ee eeeeeeeee eeee ee eeeeeeeeeeeeeee ee eeee eeeeee (Meeeee 88).[‌88‌] Meeeeee ee eeeee eeeeeeeeeeeee ee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeee eeeeeeeeee, eee eeeeeeee eee eeeeeeeee ee eeeee.

Meeeee 88 Meeeeeeee ee Meeeee Meeeeeeeeeeeeeeeeeeeeeee ee Meeeeeeee eeee Meee(MM) Meeeeee ee Meeeeeeee Meee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Mee[8-(8-eeeeeeeeeeee)-8,8-eeeeeeeeeeeeee]eeeeeee [88, M8=M8=8-MeM8M8MM(e-Me)]; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee eeeee ee eeeeeee eeeeeeee ee eeeeeeeeee eee ee eeeeeeeeee.

8,8-Mee[8-(8-eeeeeeeeeeee)-8,8-eeeeeeeeeeeeee]eeeeeeeee (8.88e, 88.8eeee) eee eeeee ee e eeeeeeeeee ee eee eeeeee MeM (8.88e, 88.8eeee) ee eee Me8M (888eM) eee eee eeeeeeeeee eee eeeeee ee eeeeee eeeeee. Meeee 88e, eee eeeeeee eee eeeeeeee eeeeeee eeeeee eee eee eee eeeeeee eee eeeeee eeee Me8M. Mee eeeeeeee eeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeeee eee eeeeeeeeeeeeee [MMe8 (MMMMMMM: eeeee)]; eeeee: 8.88e (88%); ee 888°M.

Meeee 8-(8-Meeeeeeeeeeeee)eeeeeeeeeeeeeeeeee (88, M8=8-MeeMM; M8=MMe); Meeeeee Meeeeeeee:[‌888‌]

MMM (888ee, 8.88eeee) eee eeeee eeeeee ee e eeeeeee eeeeeeeeee ee eeeee 8-(8-eeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee (88, M8=8-MeeMM; M8=MMe; 8.88e, 8.88eeee) ee MM8Me8 (88eM) eee eeeeeeee (888ee, 88.8eeee) ee ee. Mee eeeeeee eee eeee eeeeeee ee ee eee e eeeeeee 88eee. M8M (88eM) eee eeeee MMe (8eM) eeee eeee eeeee. Mee eeeeeee eeeee eee eeeeeeeee eee eeeeee eeeeeeeeeeeee eeee e eeee ee Me8M8M88M8M (8.8e) ee M8M (88eM), eee. ee MeMMM8 (88eM), eee M8M (88eM). Mee MM8Me8 eeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeeeeee; eeeee: 8.88e (88%); ee 88.888°M.