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3.4.2.6.4 Variation 4: Sonogashira–Hagihara Coupling Reactions in Oligomer and Polymer Synthesis

DOI: 10.1055/sos-SD-003-00274

Heaney, H.; Christie, S.Science of Synthesis, (20043439.

The study of conjugated polymers is of interest because of potential applications in a number of areas such as nonlinear optical properties, electroluminescence, and high conductivity after doping. Palladium/copper(I)-catalyzed alkyne coupling reactions have been utilized in a number of these areas.[‌843‌] Very efficient syntheses of a number of shape-persistent molecular systems have been reported.[‌844‌] For example, the synthesis of caltrops, a tetrahedral four-pointed device that is attached by three prongs while leaving the fourth projecting, has been reported using silicon as the tetrahedral atom with arylethynyl residues radiating from it. Thiol groups were incorporated to allow attachment to a metal surface.[‌845‌] Similarly, a reaction of tetrakis(4-iodophenyl)methane with 2-benzyloxy-6-ethynylpyridine, followed by deprotection using trifluoroacetic acid and crystallization from a mixed solvent system such as butanoic acid/methanol/hexane, induced self-assembly to give a diamondoid network.[‌846‌] The same iodide, tetrakis(4-iodophenyl)methane, has also been used in the synthesis of dendritic polyalkynes that give products with the incorporation of up to 40 cobalt atoms after reaction with octacarbonyldicobalt.[‌847‌] 1,3-Bis(arylethynyl)benzene derivatives, especially those that carry additional substituents at the 2- and 5-positions, are particularly useful building blocks for the synthesis of macrocycles and polymers that have interesting ligating properties. As mentioned in connection with the reaction shown in Scheme 149, the loss of a phenolic protecting group can give rise to benzo[b]furan formation in reactions of protected 2-iodophenols. Experiments using a number of differently protected derivatives of ethyl 4-hydroxy-3,5-diiodobenzoate showed that the best results are obtained when using 4-methoxybenzyl ether as the protecting group (e.g., to give 51), in which case benzofuran formation does not exceed 6% in any of the examples reported (Scheme 177).[‌657‌]

Meeeee 888 Meeeeeee ee Meeee 8,8-Meeeee-8-[(8-eeeeeeeeeeeee)eee]eeeeeeee eeee 8-Meeeee-8-eeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeeee eeeeeeeeee eeeeeeeeeeeee eeeeeeeeeee eeee e eeeeee ee eeeeeeeee eeeeeeeeeeeeeee, eeee ee eeeee eee eeeee eeeeee, eeeeeee ee eeeeeeee eeeee eeeeee eee eeeeeeeeee eeee eeee eeeeeeee ee e eeeeeeeeee eeeeeeee eeeeeeee eeee eeeeeeee MeeeeeeeeeeMeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeee eeeeeeeeeeeee eeeeeeeeeee.[‌888‌] Mee eeee eee eeeeeeee ee eee eeeeeeeee ee e eeeeee ee eeeeeeeeeee eeeeeeeeeee eeeeeeeee eeeeeeeeee eeee eeeeeeee e eeeeeeee ee eeeeeeeee ee eeeeeeee eeeeeeeee eeeeeeeeeeeee eeeeeeeeeee, eeeeeeee eeee eee eee eeeeeeeeeeee 8,8-eeeeeee-8-eeee-eeeee-8-eeeeeeeeeee eee eeeeee eeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee ee eeeeeeeeee eeeeee eeeeeeeeeee.[‌888‌] Mee eeeeeeeeeee eeeeeeeee, eeeeeeeeee ee eee 8,8-eeeeee eeeeeee eeeeeeee eeeeeeeeeee ee eee eeeeeee eeeeeeee, eeee eeeeeeee eee eee ee eeeeeeeee eeeee eeeeeeeeee ee eee eeee ee e 8-eeee-8,8-M,M-eeeeeeeeeeeeeee. Mee eeeee eeeeeeeeeee eeee ee eeeee ee Meeeee 888.

Meeeee 888 Meeeeeeee ee e Meeeeeeee Meeeeeeee ee Meeee eee Meeee Meeeeeeeeee Meee ee Meeeeeeee ee Mee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee(8), Meeeeeeeeeeeeeeeee, eee Meeeee(M) Meeeee ee Meeeeeeeeeee[‌888‌]

Meeeeeeeeee eeeee-eeeeeeeee-eeee-eeeeeeeeee eeeeeeeee eeeeeee eeee eeee eeeeeeeeeee ee eeeeeeee eeeeeeeee eeee eeeeeee eee eee ee eee eeeeeeeee/eeeeee(M) eeeeeeee eeeeeeeee, eeeeeee eeeeeeeee eee eeeeeeee ee 8-eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee eee eeee eeeeeeee eeee 8-(8-eeeeeeeeee)eeeeeeeeeeee.[‌888‌]

Meeeeeeeeee eeee eeee eeee eeeeeeee eeeee eeeeeee eeeeeeeeee eeeeeeeeeee eeeeeeee eeeee eee eeeeeeeeeee eeeeeeeee 8,8-eee(eeeeeee)eeeeeee-8,8-eeee ee e eee eeeeeeeeeeee. Mee eeeeeee eeeeee eeee eeeeeeeee ee eeeeee eee eeeeeeeeeeeeeeeee eeeeee eee eee eeeeeee eeeeeeee eeeeeeee eee eee eeeeeeee eeeeeeeee eeee eeeeeeeee eeeee eeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee eeeeeeeeee.[‌888‌] Me e eeeeee ee eeeeeee eeee eeee eeee eee eeeeeeeeeee eeeeeeeeee eeeeeee eeeeeee eee eeeeee ee eee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeeeeeeee eeee eeeeeeee ee eeeeee ee eeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeee ee eeeeeeee eeee eeeeee,[‌888‌] eee eeeeeee ee eee eeeeeeeee ee eeeee(eeeeeeeeeeeeeeeeeee) eeeeeeeeeee.[‌888‌]

Meeeee eeeeeeee eeee eeeeeee 8,8-eee(eeeeeee)-8,8-eeeeeeee, 8,8-eee(eeeeeee)-8,8-eeeeeeeee, eee 8,8-eeeeeeee-8,8-eeeeeeeeeeeee eeeeeeee eeee eeee eeeeeeee eeeee eeeeeeeee/eeeeee(M) eeeeeeeee ee eeeee ee eeee eeeeeeeee π-eeeeeeeeee eeeeeeee,[‌888‌] eeeeeeeee eeeee eeeee eeeeeeeeeee e8 eeeeeeeeee eeeeee eeeeeeee ee e 8,8-eeeeeeeee eeee.[‌888‌] Meeeeeeee eee eeeeeeeeee eeeeeeeeee eeee eeee eeee eeee ee eeeeeee eeeeeee eeee(eeeeeeeeeeeeeeeeeee)e.[‌888‌,‌888‌] M eeeeeee eeeeeeee eee ee eeeeeeeee ee eeeee-eeeee eeeeeeeee eee eeee eeeeeeee ee eeeeeee e eeeeeee ee eee eeeeeeeeeee eeeee, eeeee eeeeeee eeeeee eeee eeeeeeeeeeee eeee eee eeee eeeeeeee ee eeeee ee eeeeeee eee eeeeeeeeee ee eee eeeeeee,[‌888‌] eee eee eeee eee eeee eeeeeeee ee eeeeee e eeeeeee eeee 88 eeee-eeeeee eeee eeeeeeee ee e eeeee eeeeeeeeeeeee eeeeeeeee.[‌888‌] Me eee eeeeee eeee eee MeeeeeeeeeeMeeeeeee eeeeeeee eeeeeeeee eeee eee eeeeeeeee ee eeeeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeeee eee 8-eeeee-8-eeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee ee eee eeeeee eeeeee.

Meeee-eeeeeeee eeeeeeeee eeee eeee eeee eeee ee eeeeeee eeeeee eeeeeeee ee eeeeeeeee eeeeeeeee ee eee(eeee eeeeeeeeeeeeeeeeeeeeeeeeee) eeee eee(eeeeeeeeeeeeee)eeeeeee,[‌888‌] eee eee eeeee eeeee-eeeee eeeeeeeee ee eeee-eeeeee eeeeeeeeeeeee eeeeeeee eee eeee eeeeeee eee ee eeeeee e eeeeeeee ee 888-Å eeeeee.[‌888‌] Meeeeee eee eeee eeee eeeeeeeeee ee eee eee ee 8-eeeee-8-eeeeeeeeeee eee eeee eeeeeeeee eee eeee eeee eeee eeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeeee ee eee-eee eeeeeeeeeeee ee eeeee ee eeeee eee eeeeeeeee eeeeeee eeeeeeeeee ee e eeeeeeeee eeeeeeeeee eeee eee e eeeeeeeeeeeee eeeee ee eee eee eee e eeeee eeeee ee eee eeeee.[‌888‌] Mee eeeee eeeeeeeeee eee eeeeeeeee ee eeeeeeee 8-eeeeeee-8-[(eeeeeeeeeeeeee)eeeeeee]eeeeeee eeee e eeeeeeee Meeeeeeeee eeeee eeeeee e 8-(8-eeeeeeeeeeeee)-8,8-eeeeeeeeeeeee eeeee eeeee eee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee(8), eeeeeeeeeeeeeeeeee, eee eeeeee(M) eeeeee ee eee eeeeeeee eeeeee ee e eeeeeee ee eeeeeeeeeeeeeee eee eeeeeeeeeeee. Meeeeee eeeeeeee eeeeeeeee eeee eeee eeeeeeee ee eeeeeee e eeeeeeeeeeee eeee eeee eeeeeeeeeeee 8,8-eeeeee eeeeeee eeeeee.

M eeeeeeeee eeeee-eeeee eeeeee eee eee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee eee eeee eeeeeeeeee eeeee eee eeeeee eeeeeeee eeeeeee ee eeeeeeeeeee eeeee.[‌888‌] Mee eeeeee ee eeeeeeeeeee eee eee eeeee ee Meeeee 888. Meeeeee eee eeeeeeee eeeeeeee eeee eeeeeeeeeee ee 888°M eeeeeeeee eee eeeeeee ee eee eeee eeeeee eeeeee eee eeeee eeeeeeee eeee.[‌888‌] Mee eeeeeee eeeeeeeee ee eeeeeeee, eeeeeee eeeeee, eee eeee, eeeeeeeeee ee eeeee eee eeeee, ee eeeeeeeee ee eee eeeeeeeeee. Meeeeeee (8,8-eeeeeeeeeeeeeeeeeeeeeee)(eeeeeeeeeeeeeeee)eeeeee eee eeeee ee eeeee eeee 8,8-eeeeeee-8,8-eeeeeeeeeeeee ee eee eeeeeeee ee eee(eeeeeeeeeeeeeeeeee)eeeeeeeee eeeeeeeeee, eeeeee(M) eeeeee, eee eeeeeeeeeeeeeeee ee eeee eeeeeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeee eeeeee eeee e eeee eeeee ee eee eeeeeeeee eeeeee eeeeeeee eee eeee eeeeee. Meeeeee, ee eeeee eeeeeeeee eeeeeeee eeeeeeeeee, eeeeee eee eee eeeeeeeeeeee ee eeeeeeeeee ee eee eeee, e eeeeee eeeeeeeee eeeeee ee eeeeeeee ee 88% eeeee eeee e Me ee 8.88×888e·eee8. Meeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeeee eeeee e eeeeeee ee 88% eeeee eeee e Me ee 8.88×888e·eee8. Mee eeeeeeee eeee ee eeeeeeeeee eeeeeeee ee eeee eeee eeee eeeeeeeee eeeeee eeeeeeeeeee eeeeee.[‌888‌] Meeeeeee 8-eeeeeee-8,8-ee(8-eeeeeee)eeeeeee ee 8-eeeee-8-(eeeeeeeeeeeeeeeeeeeee)eeeeeee eee eeee eeee ee eeeeeee eee eee eeeee eeeeeee eeee ee e eeeee-eeeeeee eeeeeeeeeeeeeeee eeeeeeee. Mee eeeee eeeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee ee eee eeeeeeee eeeeeeee.[‌888‌] Mee eeeeeeeee ee eeeee 8,8-eeeeee eeeeeee eee 8,8-eeeeee eeeee-eeeeeeeeee eeeeeeeee eee eeee eeeeeeee eeeeee eee ee MeeeeeeeeeeMeeeeeee eeeeeeee eeeeeeeee.[‌888‌]

Meeeee 888 Meeee-Meeee Meeeeeeee ee Meeeeeeeeeeeeee Meeeeeeeeee Meeeeeeee ee Mee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee(8), Meeeeeeeeeeeeeeeee, eee Meeeee(M) Meeeee ee Meeeeeeeeeeee[‌888‌]

eeee-Meeeee eeeeeeeee eeee eeee eeeeeeee eeeee eeeeeeeeee eeeeeeeeeee eeeeeeeee[‌888‌] ee eeeeeee, eee eeeeeee, ee eeeeeeeeeee, eeeee eeeeee e eeeeeee eeeeeeeeeeee eeee ee eeeeee ee eeeeeeeeeee eeeeeeeeeeee eee ee eeeeeeeee ee eeeee eeeeee, eeeeeee, eee eeeeeeeeeee.[‌888‌] Meeeeeeeee-eeeee eeeeeeeee eeee eeeeeeee eeeeeeee eeeeeee eee eeee eeee eeeeeeee eee e-eeeeeeeee eeeeeeeeee eeeeeeeee.[‌888‌] Mee eeee eee eeee eeeeeee eeeeeeee ee eeeeeee eee eeeeee ee eeeee eee eeeeeeeeeeee, eee eeeeeee ee eeeee eeeeee eeeeeeeeeeeeeeeeeeeeeeeee.[‌888‌] Mee eeeeeeeeeee ee eeeeeeeee eeeeee eeeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeeeeee ee e eeeeee ee eeee eeee eeeeeee eee eee ee eeeeeeeee/eeeeee(M) eeeeeeeee. Me eee eeeeeeeee ee eee eeeeeeeee ee Meeeeee 8.8.8.8.8 eeee eeeeeeeee ee eeee eeeeeee eeee eeeeeee eeeeeeeee eeee ee eee eeeeeeeee ee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeeee.[‌888‌] Meee eeee ee eeeeeeee eee eeee eeee ee eeeeeee e eeeeee ee eeeeeeeee eeeeeeeeeeeeee eeeeeeee, eeeeeeeee eee eeeee ee eee eee ee eeeeeeeee eeee (M)-8,8-eeeeee-8,8-eeeeeeeee-8,8-eeeeeeeeee,[‌888‌] eee eeee eeeeeeeeeee ee 8,8-eeeeeee-8,8-eeeeeeeee-8,8-eeeeeeeeee eeee eeee eeee eeeeeee eee eeeeeee 8,8-eeeeeeeee-8,8-eeeeeeeee-8,8-eeeeeeeeee, eeeee ee eeeeeeeee eeeeeeeeeeeeee.[‌888‌] Meee eeeeeeeee eeeeee eeeeee eeeeeeeeeee eeeeeeee eee eeeeeeeee eeeeeeeee eeee eeee eeee eeeeeeee eeeeeeee eeee 8,8-eeeeeeee-8,8-eeeeeee-8,8-eeeeeeeeee eeeeeeeeeee.[‌888‌] 8,8-Meeeeee-8,8-eee(eeeeeeeeeeeeeeee)-8,8-eeeeeeeeee eee eeee eeee ee eeeeee e eeeeee eeeeeee eeee e eeeeeeee eeeee ee eeeeee e eeeeee eeee ee eeeeeee eeeeeee,[‌888‌] ee eeee eee e (+)-eeeeeeee-eeeeeee eeeeee.[‌888‌] Mee eeeeeeee eeeeeeeeeee ee eeeeeeee eeeeee eee eeee eeeeeeeee ee eee eeeeeeeee ee e eeeeee ee eeeeee 8,8-eeeeeeeee-8,8-eeeeeeeeee-eeeeeee eeeeeeeeeee.[‌888‌] Mee eeeeeeeee eeeeeeeeee eeee eeee eeeeeeee ee eeee eee eeeee eeeeeeee eeeeeeeeeee eeee eeeeeeeee eeeee eeeeeeeee/eeeeee(M)-eeeeeeeee eeeeeeee eeeeeeeee eee eee eeeeeeee eeeeeeeee MeeeeeMee eeeeeeee ee eeeee eee eee eeee ee eee eeeeeeeee eeeeeeeee, eee M8-eeeeeeeeeee (+)-(M,M,M)-eeeeeeee, ee Meeeee 888.

Meeeee 888 Meeeeeeee ee e Meeeeeee 8,8-Meeeeeeeeeeee-Meeeeee Meeeeeeeee Meeeeeee[‌888‌]

Meeeeeeee eeeeee eeeee eeeee eeeeeeeeeee eeee eeee eeee eeeeeeee. Meeeeeee (M)-8,8-eeeeeee-8,8-eeeeeeeee-88-eeeee-8 eeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeeeeeeeeeeee eeeee e eeeeeeeeee eeeeeee eeeeee eeeeeeeeee eeeee eeeee eeeeeee eeee Me=88888 ee e eeeeeeee eeee eeee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee, eeeeee(M) eeeeee, eee eeeeeeeeeeeee ee eeeeeee,[‌888‌] eee eeeeeeeeeee eee eeeeeeee ee eeeeeeeee, eee eeeeeee, eeeee 8,8-eeeeee 8,8-eeeeeeeeeeeeeeee eeeee eeeeeee eee eeeeeeeeee-eeeeeee eeeeeeee.[‌888‌] Meeeeee eeeeeee eeee eeeeeee eeeeeeee eeee Me=88888[‌888‌] eee eeeeeeee eeee eeeeeeeee-eeee eeeeeeeeee.[‌888‌]

Mee eeeeeee ee eeeeeeeee eeee eeeeeee eeeeeeeee eeeeeeeee ee eeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee eee eee ee eeeeeeeeee eeeee ee eeeee eeeeeee.[‌888‌‌888‌] Mee eeeeeeeeeeee, eeeeeeeee/eeeeee(M) eeeeeeee eeeeeeeee ee eeeeeee eeee eeee eeeeeee eeee eeee eeee eeee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeee. Mee eeeeeee, e eeeeee 88-eee eeeeeeeeee eeee e eeeeeeeee eeeeee ee 88eM eeeee ee eeeeeeeeeeeee eeeee eee eeee eeeeeeee.[‌888‌] Me eeeee ee eeeeee eeeeeeeeee eeeeeeeeee ee eee eeeee eeeeeeeee ee eeeeeeeeeee 8,8-ee-eeee-eeeeeeeeeee eeeeeeee eee eeeeeeeee ee eeee eeeeeee eeee eeeeeeeee eeeeeee eeeeeeeee eeeee ee eeeeeee eee ee eeeee eeeeeeeeeeee eeee eeeee eeee eeeeeee eeee eeeeeeee. Meee-eeeeeeee ee eee eeeeeeeeeeeee ee eeeeeee e eeee-8,8-eeeee eeeeeee eee eeeeeeeee ee eee eeeeeee eeeeeeeee ee eeeeeeee. Mee eeeeeeee eee eeee eeeeeeee ee eee eeeeeeeeeee ee e eeeeeeeeee eeee e eeeeeeeee eeeeeeee ee 88.8ee eee eeeeeeee eee eee ee 8,8-eee(eeeeeee) eeeeeeee eeee eeeeeeee 8-eeeeeeeeee-M,M-eeeeeeeeeeeeeee ee e eeeeeeeee eeee ee eee 8-eeeeeeeeeeeeeeeeeeee eee eeee eeeee ee eeeeeeeee eeee ee eeee eeeeeeee ee e eeeee eeeee.[‌888‌] Meeeeeeeeee eee eeee eeeeeeee eee eeee eeeeeeeee ee e eeeeeeeeee eeeeee eeeeee eeee eeeeeee e eeeeee eeeeeeeeeeeee eeeeeee, M,M-eeeeeee-8,8-eee[(eeeeeeeeeeeeee)eeeeeee]eeeeeeeeeeeeee. Mee eeeeeee eee ee eeeeeeeee eeeeee eeee 8-eeee-8,8-eee[(eeeeeeeeeeeeee)eeeeeee]eeeeeee ee eeee M,M-eeeeeee-8,8-eee(eeeeeee)eeeeeeeeeeeeee.[‌888‌] Mee eeeeeeeeeee ee eeeeeeeee eeeeeeeee eeee eeee ee eeeeeeee eee eeeeeeeeeee eeeee-eeeeeeee eeeeee eeeeeeeee eee eeeeeeeeeee ee eeeeeeeeee eeeee eee eeeeeeeeee eeee e eeeeeeee eeeeeee eeee eee eee ee e eeeeeeee ee eee eeeeeeeeee ee eeeeee eeeeeeee ee eeeeeeeeeeee. Meeeeeee eeeeeeeee ee 8-eeeeeeeeeeeeeee eeee eeeeeee eee eeeee e eeeeee ee eeee-eeeeeeeeee eeeeeeeeeeee eeeee eee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee, eeeeeeeeeeeeeeeeee, eee eeeeee(M) eeeeee ee eeeeeeeeeeeee.[‌888‌]

M eeeeee ee eeeeee eeeee-eeee eeeeeeeee eeeeeeeee eeee eeee eeee eeeeeeee eeeee eeeeeeeee/eeeeee(M)-eeeeeeeee eeeeeeee eeeeeeeee ee eeeee ee eeeee eee eeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee ee eee eeeeeee eeeeeeeeee ee eeeee eeeee eeeeeeeeee.[‌888‌] M eeeeeeeee eeeeee eeee eee eeeee (+)-(M)-8,8-eeeeee-8,8-eeeeeeeeeeeee-8,8-eee(eeeeeeeeeeeee) eeeee eee eee eeeeeeeeee eeee ()-(M)-8,8-eeeeeeeee-8,8-eeeeeeeeeeeee-8,8-eee(eeeeeeeeeeeee) eeeee;[‌888‌] eeeeeeeeee ee Meéeeee-eeee[‌888‌] eeeeeeeee eeeeeeee ee eeee eeeeeeee ee eeeeeeeeeee ee Meeeee 888.

Meeeee 888 Meee ee eee Meeeeeeee ee e 8,8-Meeeeeeeeeeee-Meeeeee Meeeeeeee Meeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeee 8,8-Mee[(8-eeeeeeeeeeee)eeeeeee]-8-[(8-eeeeeeeeeeeee)eee]eeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

MeMe8(MMe8)8 (88ee, 8.888eeee) eee MeM (88ee, 8.888eeee) eeee eeeee ee e eeeeeeee eeee ee eeeee 8,8-eeeeee-8-[(8-eeeeeeeeeeeee)eee]eeeeeeee (8.8e, 8.88eeee) eee 8-eeeeee-8-eeeeeeeeeeeeee (8.8e, 8.88eeee) ee eeeeeeeeee (88eM). Meeeeee eeee ee eee eeee eee e eeeee eeee eeeeeeeee eee eeeeeeee. Meeee eeeeeeee ee ee eee 8e eee eeeeeee eee eeeeee eeee ee eee eeee eee M8M eee eeeee. Mee eeeeeee eee eeeeeeeee eeee Me8M/MMM eee eee eeeeeeee eeeeeeee eeee eeeeee eeee eee. eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee. Meeeeeeeee eeeeeee eeeeee eee (eeeeeeeee eeeee/Me8M 8:8, Me 8.88) eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM) eeee 88 ee ee eee-eeeee eeeee; eeeee: 8.8e (88%); ee 888.8888.8°M.

References


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