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17.9.2.1 Method 1: From Phthalonitrile

DOI: 10.1055/sos-SD-017-01835

McKeown, N. B.Science of Synthesis, (2004171249.

Phthalonitrile is a common starting material for the synthesis of metal phthalocyanines (Scheme 10). Either the metal or a metal salt is used for the cyclotetramerization reaction, which can be carried out either in the melt (bulk reaction) or in a high boiling solvent such as quinoline, 1-chloronaphthalene, or 1-methylpyrrolidine. The use of a solvent prevents halogenation of the phthalocyanine macrocycle if using a metal halide salt. High-boiling protic solvents, such as pentanol or 2-(dimethylamino)ethanol, can also be used especially if promoted by a catalytic quantity of a hindered base, such as 1,8-diazabi­cyclo[5.4.0]undec-7-ene.[‌57‌,‌99‌] Alternatively, methanol can be used as the solvent but high pressure and the use of a reducing agent (hydroquinone) is required to give a reasonable yield for most metal phthalocyanines.[‌98‌]

Meeee 8M: Meeeeee, eeeeee, eee eeeeeeeee eeee MeM8 eeeeeeeee (Meeeee 8) eeee eee eeeeeeee eeeeeee eeeeeeeeeeeeee eee eee eeeee eeeeeeeee ee e eeee-eeeeeee eeeeeee (e.e., eeeeeeee; eee Meeeeee 88.8.8.8.8).[‌88‌,‌88‌] MeMe8 eee MeMe8 eee eeeeee eeeeeeeeeeeee eee eee eeeeeeeeeee ee eeeee-eeee eeeeeeeeeeeeee (Meeeeee 88.8.8.8.8) eee eeeee eeeee-eeeeeeeeee eeeeeeeeeeeeeee (Meeeeee 88.8.8.8) eee ee eeeee eeeeeeeeee ee eeeeee eeeeeeee, eeee ee eeeeeee. Meeeeeeeeeeeeeeeeeee eeeeeee eee eeee e eeeeeeeeee ee eeeee eeeeeee ee e MeMM eeeeeee.[‌88‌] Meeeeeeeeeeeeee eeeeeeeee eee eeeeeee eee (Me8)Me eeeeeee eeeeeee, eeeee eeeeeeee eeeeeeeee eeeeeeeeeeee.[‌888‌‌888‌] Meeee eee ee eeeeeee ee eeeeeeeeeeeee eeeeeeee, ee eeeeee eeeeeeeeeeeeee eeeeeeeee, eeeeeee, eee eeeee-eeeee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeee ee eee eeeeeeeeeee eeeeee eeeee eeeeee eeeeeee ee e eeeeeeeeeee eeeee ee eeeee eeeeee eeeee eeeeeee eee eeeeeeeee ee eee eeeeeeeeee eeeeeeee ee eeeeeeee ee eee eeeeeee eeeeee.[‌888‌]

Meeee 8M: Meeeee MeM eeeeeeeee ee eeeeeeeee eee eeeeeeeee eee ee eeeeeeee ee eeeeeeeeee eee eeeeeee eeeeee eeeee ee e eeee ee eeeeeeeeeeeeee.[‌88‌,‌88‌,‌888‌] MeM eeeeeeeee ee eeeeeee eee eeeeee eee ee eeeeeeee eeeeeeeee eeee eee eeeeeeeeee eeeee.[‌88‌,‌88‌] MeMe ee eeeeeeee ee eeeeeeee eeeee eeee e eeeeeee e eeeeeeee ee eeeeeeeeeeeeee, eeeeeeeee eeeeeeee, eee e eeeeeeeee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeeeeeee ee eeeeee.[‌888‌]

Meeee 8M: Meeee ee eeeeee ee eeeeeee eeeeeeeeeeeeeeeeee (eee Meeeeee 88.8.88). MeMM eeeeeeeee (Meeeee 8; M=Me8+, Me8+, Me8+; M=Me, Me) eee eeeeee eeeeeee eeee eee eeeeeeee ee eee eeeee eeeeeeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeeee ee eeeeeee eeeeeeeee ee 8-eeee­eeeeeeeeeeeee.[‌888‌‌888‌] Meeeeee eeeeeeeee eeeeeee eee ee e eeee ee eeeeeeeeeeeeee eeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeeeeee eeee.[‌88‌] MeMeMM ee eeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeee eeeeeeeeeeeeee, eeeeeeee eeeeeeeeeee eee eeee ee eeeeeee ee eeeeee, eeeeeeee ee eeeeeeeeee ee eeeeeee eeeeeeee eeee.[‌888‌] Mee eeeeeeee ee eeeeee eeeee eeee e eeeeeeeeeeeeee eeee eee eeee Me8Me,[‌888‌] Me8Me8,[‌888‌] ee, ee eeeeeee eee eeeee e eee eeeeeeee eeeeeeee, e eeeeeeee[‌888‌] eeeeeeeeeeeeee eeeeeee (Meeeee 8). M eeeeeee eeeeeeee ee e eeeeee ee eeeeee eee eeeee MeMeM.[‌888‌] Meeeeeee eeeee eeeeee eeee eeeeeeeeeeeeee ee eee eeee ee eeeee eee eeeeeee MeMe8 eeeeeee (Meeeee 8), eeeee ee eeeeeee eee eee eeee eeeeeeeeee eeeeeeeeeeee.[‌888‌,‌888‌‌888‌] Me eee eeeeeeee ee eeeeeee eee eeeee e eee eeeeeeee ee eeeeeeee, e eeeeeeee eeeeeeeeeeeeee eeeeeee ee eeeeee.[‌888‌,‌888‌]

Meeee 8M: Mee eeeeee eeeee-MeMMe8 eeeeeeeee (Meeeee 8) ee eeeeeee eee eeeeeeeee eee eeee eeeeeeee ee eeeee eeeeeeeeeeeeeeeeee (Meeeeee 88.8.8.8) ee 8-eeeeeeeeeeeeee (Meeeeee 88.8.8.8) ee eeeeeeeeee. Meeeeeeeeeee, MeMeMe8 ee eeeeee ee eeeeeeeeee eeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeee eeeeeee eeeeeeeeeeeee.[‌88‌,‌888‌] eeeee-MeMeM8 ee eeeeee ee eee eeeeeeee ee eeeeeeeee eeee eeeeeeeeeeeeee ee eee eeeeeeee ee eeeeee eee.[‌888‌,‌888‌] MeMe eee eeeee-MeMeMe8 eeeeeeeee eee ee eeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eeee eeeeeeee eee eee eee(MM) eeeeeeee, eeeeeeeeeeee.[‌88‌,‌888‌,‌888‌,‌888‌] Me eeeeeeee, MeMe ee eeeeeeee eeee eee eeeeeeee ee eeeeeeeeeeeeee, eee(MM) eeeeeeee, eee e eeeeeeeee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeeeeeee eeeeee eeeeeeeeee eeeee ee eeeeee.[‌888‌] MeMe ee eeeeee eeee eee eeeeeeee ee eeee eeeee eeee eeeeeeeeeeeeee ee eee eeee[‌88‌] ee ee eeeeeee 8-eeeeeeeeeeeeeeeee eeeeeeee.[‌888‌,‌888‌] Me ee eeee eeeeeeee ee eeee eeeee eeee e eeeeeeee ee eeeeeeeeeeeeee, eee(MM) eeeeeeee, eee e eeeeeeeee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeeeeeee ee eeeeee.[‌888‌]

Meeee 8M: Mee eeeeeeee ee eeeeeee eeeee eeee eeeeee eeeeeeeeeeeeee ee e eeeeee ee eeeeee eee eeeeeeee (Me8Me)8(M8)8.[‌888‌] Meeeeeee eeeee eeeeee eeee eeeeeeeeeeeeee ee eeee e eeeeeeee, eeeee eee eeeeeeee ee MeMe8 ee Meeeeeee, eee ee ee eeeeeee eeeeeeeee.[‌88‌] Mee eeeeeeee ee eeeeeeee(MMM) eeeeeeee eeee eeeeee eeeeeeeeeeeeee eeeee [MeMeMe8]MeMe8.[‌888‌,‌888‌] Me eeeee ee eeeeeee eee eeeeeeee eeeee e Me8Me8 eeeeeee (Meeeee 8) eeee eeeeee eeeeeeeeeeeeee,[‌888‌] eeeeeee eeeeee e [Me8Me]+8.8(M8)8.8 eeeeeee[‌888‌,‌888‌] ee e [(MeMe)+]8[Me8M88]8 eeeeeee[‌888‌] ee eeeeee ee e eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeee. Mee eeeeee-eeeeee eeeeeee Me8Me8 eee eeee ee eeeeeeee ee eeeeeeee ee eeeeeeeeeeeeee eeee eeeeeee eeeeeee.[‌888‌]

Meeee 8M: Mee eeeeeeeeee eeeeee eee eeee MeMM (Meeeee 8), eeeeeeee (Me8M), ee eeeeee-eeeeee (Me8M8) eeeeeeeee (Meeeee 8); eeeee eeeeeee eeeeeeee eeeeeeeeee eee ee eeee eeeee ee eeeeeee eee eeeeeeee. Meeeeeeee eeeeeeeee MeMM (e.e., M=Me,[‌888‌] M,[‌888‌,‌888‌,‌888‌] Me,[‌888‌] Me,[‌888‌] Me,[‌888‌] Me,[‌888‌] eee Me[‌888‌,‌888‌]) eee eeeeeeee-eeee Me8M eeeeeeeee (e.e., M=M,[‌888‌] Me,[‌88‌,‌888‌] Me,[‌888‌,‌888‌] Me,[‌888‌,‌888‌] Me,[‌888‌,‌888‌] Me,[‌888‌,‌888‌] Me.[‌888‌,‌888‌]Me,[‌888‌,‌888‌] Me,[‌888‌] Me,[‌888‌,‌888‌] Me,[‌888‌,‌888‌,‌888‌] eee Me[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌]) eeee eeee eeeeeeee eeee eee eeeeeeee eeeeeeee eeeeee eeee eeeeeeeeeeeeee eee e eeeee eeee eeeeee ee eee eeee ee ee eeeeeeee. Me8M eeeeeeeee eee eeeee ee e eeeeeee eeeeeee eeeeeee (eeeee, eeeeeeee eeee) ee ee eee eeee eeeeeee eeee (Me8M) eeeeeeeeee eeee e eeeeeee eee.[‌888‌] Meeeee ee eeeeeee ee eeee ee eeeee e eeeeeee eeeeeeee eeeeeee, ee eeeee eee eeeee eeeeee ee e +8 eeeeeeeee eeeee.[‌888‌,‌888‌] Me eeeeeeee, ee ee eeeeeeee ee eeeeeee ee eeeeeeeeeeeeee eeeeee-eeeeee eeeeeeee eeeeeeeee (Me8M8) (Meeeee 8) eeee eee eeeeeee eeeeeee eeeeee eeeeeee eeeeeeeeeeeeee eee eeeeeeeeee eeeee eeeee.[‌888‌,‌888‌] Meee eeeeeee eeee eee eeeeeeeeeee ee eee eeeeeee eeeeeee ee eeeeeeee ee eeeeeee eee eeeeeeeeeeeeee eeeee ee eee eeeeeeee eeeeeeeee. Me eeeeeeee, e eeeeeeee MeM eeeeeee (M=Me, Meeeee 8) eee eeee eeeeeeee eeee eee eeeeeeee eeeeeee eee eeeee eee eeeeee eeeeeeeeeeeeee eeeee e eee-eeeeeeee eeeeeeee eeeeeeeeee.[‌888‌]

Mee eeeeeeeeee eeeee ee eeeeeeeeeeeeee eeeeeeeee eeeee eeeeeeee eeeeee eee eeeee eee eeee eeeeeeeeee ee eee eeee eeeeee eeeeeee ee eee eeeeee.[‌888‌] Meeeeeeee, eeeeee eeeeeeeee eeeeee eee eee eeeeee eee eeeee eeeeee eee eeeeeeeee ee eeeeeeee ee eee eeeeeeeeee eeeeee. Meeeeee eeeeeee eeeeee ee eee eeeeeee ee eeee eeeeeeeeeeeeeeeeeeee (Meeeeee 88.8.88). Mee eeeeeeee ee eeeeeeee eeeeee ee eeeee eeee eeeeeeeeeeeeee eeeee e Me8M eeeeeee (e.e., M=Me,[‌888‌‌888‌] Me,[‌888‌] M,[‌888‌,‌888‌] Me[‌888‌]) ee eeeee eee eeeee eeeeeeeee e +8 eeeeeeeee eeeee. Meeeeeeee eeeeeeeeeeeeee eee ee eeee ee eeeeeee Me8888Me eee Me8888Me eeee Me8888Me eee Me8888M, eeeeeeeeeeee.[‌888‌]

Meeee 8M: Mee eee-MeMMe8 eeeeeeeee (M=Me,[‌888‌,‌888‌] Me,[‌888‌] Me;[‌888‌] Meeeee 8) eee eeeeee eeee eee eeeeeeee ee eee eeeee eeeeeeee eeee eeeeeeeeeeeeee ee e eeeeeeee eeeeeee. Mee eee ee e eeeeeee, eeee ee 8-eeeeeeeeeeeeeeeee, eee eeeeeee eeeeeeeeeeee ee eee eeeeeeeeeeeeee eeee.[‌888‌] Meeeeeeeee ee eee eeeee eee-MeMMe8 eeeeeee eeee eeeeeee eeee eeeeeeee MeMeM,[‌888‌] eee-MeMe(MM)8, eee eee-MeMe(MM)8,[‌888‌] eeeeeeeeeeee. Meeeeeeeeeeee, MeMeM eee MeMe(MM)8 eee ee eeeeeeee eeee eee eeeeeeeee eeeeeee eeeeeeeeeeeeee eee eeeeeeee(MM) eeeeeeee ee eeeeeeeee(MM) eeeeeeee, eeeeeeeeeeee, eeeeeeee ee ee eeee eeee eeeeeeeeee.[‌888‌] Meeeeeeee eeeee eeeeee eeee eeeeee eeeeeeeeeeeeee ee e eeeeee ee eeeeee eee ee eeee eee-MeMM8.[‌888‌]

Meeee 8M: Meeeeeee eeeee eeeeee eeee eeeeee eeeeeeeeeeeeee ee eeee MeMM.[‌88‌] Meee eeeeeeee eee eeee ee eeeeeeee ee eeeeeeeeee ee eee eeeee eeeeeee eeeeee ee eee eeeeeeee eeeeeee eeeeeeee(MMM) eeeeeeee eee eeeeee eeeeeeeeeeeeee.[‌888‌] Meeeeeee eeeee eeeeee eeee eeeeeeeeeeeeee ee e eeeeee ee eeeeee eee ee eeee MeMM.[‌888‌] Meeeeee[‌888‌,‌888‌] ee eeeeeeee[‌888‌] eeeeeeeeeeeee eeeee ee eeee eee eee-MeMMe8 eeeeeee (Meeeee 8). Meeeeeeee, eee-MeMeMe8 eee ee eeeeeeee eeeee eeeeeee(M) eeeeeee,[‌888‌] eeeeeee, eeeeeee(M) eeeeeeeeee eeeee e eeeeeee eeeee, ee eeeee eeeeeeee eee eeeeeee eeee eee eeeeeeee eeeeeee eee eeeeeeeeeeeeee eeeeeeeeeee.[‌888‌]

Meeee 8M: Meeeeeeeeeeeee eeee eee eeeee eeeeeee eeee eeeeeeee eeeee,[‌88‌] ee eeee eeeeeee eeeee,[‌88‌,‌888‌] eee ee eeee eeeee eeee eeeeeeeeeeeeeeeeeeee ee eeee MeMe, eeeee eeeeeeee ee MeMeMM ee eee.[‌888‌] Meee eeeeeeee ee eeeeeee eeeeeeeeee ee eeee eee (MeMe)8M eeeee (Meeeee 8). M eeeee ee eeeeeeeeee eeeee eeeee eeee eeeeeeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeee eeee eee eeeee ee eeeeeee eeeeeeeee eeeeee. Meeeeeee eeeee­eeee(MM),[‌888‌,‌888‌] eeeeeeeeeeeeeeeeeeeeee,[‌888‌] eee eeeeeeeeee(MM) eeeeeeee[‌888‌] eee eeee MeMe=M ee eeeeeee eeeeee. MeMeM8 ee eeeeeeee eeeee eeeeeeeeee eeeeeeee(eeeeeeee­eeeeeee).[‌888‌]

Meeee 8M: Meeeeeeee eeeee, eeee ee eeeeeeeee(MM) eeeee, eeeeeeeee eee(eeeeeeee­eeeeeee), eeeeeeeee(MM) eeeeeee, ee eeeeeeeee(MM) eeeeeeee, eeeee eeee eeeeeeeeeeeeee, eeeeee ee eee eeee ee ee eeeeeeee, ee eeee MeMe,[‌88‌,‌88‌] ee MeMeMe,[‌888‌] eeeeeeeeeeee. MeMeMe ee eeeeeeeeee ee MeMeMM ee ee eeeeeee eeee eeeeee.[‌888‌] Mee eeeeeeee ee eeeeeeeeeeeeee eeee eeeeeeeee(MM) eeeeeeee ee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee 8,8-ee­eeeeeeeeee[8.8.8]eeeee-8-eee eeeee eeeeeeeeeeeeee ee eeee eeeee.[‌888‌] Mee eeeeeeeeee eeee eeeeeeee eeeeeeeeeeeee [Me(MM8)M8] eeeeee eeee eeeeeeeeeeeeee ee eeee MeMeM (Meeeee 8).[‌888‌] Meeeeeeee, eeeeeee eeeee eeee ee eeeeeeee eeeeeeeeee eeeee eeee eeeeeeeeeeeeee ee eeeeeee MeMeM.[‌888‌‌888‌]

Meeee 8M: Meeeeeeeeeeeee eeeeee eeee e eeeeeee ee eeee-eeeeeeeeee eeeeeeee, eeeeeeeee eee eeeee eeeeee,[‌88‌] ee eeee MeMe. Meeeeeeeeeee eeeeee eee eeeeeeeee[‌88‌] eee eeee eeeeeeeeeeeee.[‌888‌] Mee eeeeeeee ee eeeeeeeeeeeeee eeee eeee(MM) eeeeeeee ee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee eeeee e eeee eeeee ee MeMe.[‌888‌] Mee eee ee eeee-eeeeeeee[‌88‌] ee eeeeeeeee eeeeeeeeeee[‌888‌] eee eeeeee eeeeeeeeeeeeee eeeeeeeee. MeMe ee eeeeeee eeeeeeee ee eee (MeMe)8M eeeee (Meeeee 8).[‌888‌] Mee eeeeeeeeeee ee eeee eeeeeeeee eeeeeeeeeeeeee, eeeee eee eeee eeeee ee eeeee ee eee eeee MeMe=MeMe ee eee eeeee eeeee,[‌888‌] ee eee eeeeeeeeeeeeeee. M eeeee eeee ee MeMe eee ee eeeeeeee eeee eeeeeeeeeeeeee eeeee eeeeeeeee(MMM) eeeeeeee eeeeeee.[‌888‌‌888‌] Meeeeeee ee eeeee eeeeeee eeee ee eeeeeeee eeeeeeeee,[‌888‌] eeeeeeee,[‌888‌] ee eeeeeeeeeeee[‌888‌] eeeeeee eeeeeeeeee ee eeee eeeeeeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeeeeee eee ee eeeeeeee. Meeeeee ee eee eeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee eeeee eeee MeMe. Mee eee ee eeeeeeeeee eeeeeeeee ee eeeeeee eee eee eeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeee eeee eeeeeeeeeeee ee eee eeeeeeeeeeeeee eeee ee eeeeeee eee eeee eeeeeeee ee eeeee eeeeee ee eee eeee ee eeeeeeeeeeee eeeee ee eeeeeee ee ee eeeeeeee eeeeee eeee eeeeeee ee eeeeeeeeeee eeeeeeeeee.[‌888‌] Meeeeee eeeeeeeeee eee eeee eee eee eeeeeeeee ee eeee MeMe eeee eeeeee-eeeeeeeeee eeeeeeee eeee ee eeeeeeeeeeeeeeeeeeeeeee eee eeeeee eeeeeeeeeeeeee;[‌888‌] eeeeeee, 8-eeeeeeeeeeeeee ee eee eeee eeeee eeeeeeee eeeeeeee eee eeee eeeeeeeeeeeeee (Meeeeee 88.8.8.8).

Meeee 8M: Meeeeeeeeeeeee eeeeee eeee eeeeee eeeeee eeeee ee eeee MeMe.[‌88‌] Meeee eeeeeeee eeeeeeee eee eeeeee(MM) eeeeeee,[‌888‌] eeeeee(MM) eeeeeeeeeeeeeee,[‌888‌] eeeeee(MM) eeeeeee,[‌888‌] eee eeeeee(MM) eeeeeee.[‌88‌] Meeeee(MM) eeeeeeee eeeeee eeee eeeeee eeeeeeeeeeeeee ee eeee eeee­eeeeeeeeeee MeMe[‌88‌] eee eee eeee eeeeeee eee ee eeee ee eeeeeeee ee eeee eeeeeeeeeeeee MeMe.[‌888‌] Mee eee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee,[‌888‌] eeee eeeeeeee,[‌88‌] ee eeeeeeeee eeeeeeeeeee[‌888‌] eee eeeeee MeMe eeeeeeeee. MeMeMe[‌888‌,‌888‌] eee MeMeMe[‌888‌] eee ee eeeeeeee ee eee eeeeeeee ee eee eeeeeeeeeee eeeee eeeeeeee eeee eeeeee eeeeeeeeeeeeee.

Meeee 88M: Meeeee eeeeee eeeeeee eeeee MeMe eeee eeeeee eeeeeeeeeeeeee.[‌88‌,‌88‌] Meeeeeeee, eeeeee(MM) eeeeeeee (eeeeeeee[‌888‌] ee eeeeeeeee[‌88‌]), eeeeee(MM) eeeeeee,[‌88‌] eeeeee(MM) eeeeeee,[‌888‌] eee eeeeee(MM) eeeeeeeeeeeeeee[‌888‌] eee ee eeee ee ee-eeeeeeeee. Mee eee ee 8,8-ee­eeeeeeeeee[8.8.8]eeeee-8-eee,[‌888‌] eeee eeeeeeee,[‌88‌] ee eeeeeeeee eeeeeeeeeee[‌888‌] eee eeeeee MeMe eeeeeeeee. M 88M-eeeeeeee MeMe eee eeee eeee eeee eeeeeeee eeeeeeeeeeeeee.[‌888‌] Meeeee eeeeeeeeeeeeee eeeeee eeee eeeeeeeee eeeee ee eeee MeMe.[‌88‌] Meeeeee, eeeeeeee eeee eeeeeeeee eeeeeeee eeeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeeeeee eeee.[‌88‌] Mee eeeeeeee ee eeeeeeee(MM) eeeeeeee eeee eeeeee eeeeeeeeeeeeee eeeeeeee MeMe.[‌88‌]

Meeee 88M: Meeeee eeeeee eee eeee eeeeee eeeee [e.e., MeMe, MeMe8, MeMe, eee Me(MMe)8] eeeee eeeeeeeeee eeee eeeeeeeeeeeeee eeeeee ee eee eeee ee ee eeeeeeee.[‌88‌] Meeee eeeeeeeee eeee eeee eeeeeeee eeeee eeeeeee eeeeeeee.[‌88‌] Mee eeee eeeeeeee ee eeeeee(MM) eeeeeeee eeee eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee ee eee eeeeeeeeee. Mee eee ee e eeeeeee eeeeee eeee eeeeeee. Meee, e eeeeeeeee eeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee 8,8-eeeeeeeeeeee[8.8.8]eee-8-eee eeeeeee e eeee eeeee ee MeMe ee ee eeeeeeee eeee eeeeee(MM) eeeeeeee eee eeeeeeeeeeeeee ee e eeeeeeee ee eeeeeeee ee eeeeee; eeeeeeeeee eeeeeeeeeeee eeee eee eeeee.[‌88‌] Me eeeeeeee, eeeeeeeeeeeeeee eeeeeee ee eeeeeeeee[‌88‌,‌88‌] eee eee eee ee eeeeeeeee eeeeeeeeeee[‌888‌] eeee eeee eeeeeeeeeeee.

Meeee 88M: Meee eee eeeeeee eeeee eeeeeeeeeeee eeeee eeee eeeeeeeeeeeeee ee eee eeee ee eeee MeMe eee MeMe, eeeeeeeeeeee.[‌88‌] M eeeeeee eeeeeeee ee eee eeee eeee eeee(MM) eeeeeeee eeeee e eeeeeeeeeeeeeee eeeeeeee.[‌88‌] Meeeeee, eeee(MM) eeeeeeee eee eeeee­ee(MM) eeeeeeee eeee MeMe eee MeMe, eeeeeeeeeeee; eeee eeeeeeee eee eeeeee ee eeee eeeeee eeee eeeeeeeee eeeeeeeee ee e eeeeeeee ee eeeeeeeeeeeeee ee eeeeeeee ee eeeeee ee eee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee.[‌888‌] Mee eeeeee ee eeee eeeeeeee[‌88‌] eee eeeeeeeee eeeeeeeeeee[‌888‌] ee eee eeeeeeeee ee eeeee eeeeeeeee eee eeee eeeeeeeeeeee.

Meeeee 88 Meeeeeeeeee ee MeeeeMeeeeeeeeeeeee Meeeeeeee eeee Meeeeeeeeeeeee[‌88‌,‌88‌,‌88‌,‌888‌,‌888‌,‌888‌]

Meeeeeeeeee 88

M Meeeeee Meeeeeeeee Meeee (%) Mee
Me MeMe8 Me, eeeeeeee, eeeeee, 88eee 88 [‌88‌]
Me MeMe MeMe8, MMM, eeeeeeee, eeeeee, 8e 88 [‌888‌]
Me MeMe MeMe, MMM, eeeeeeee, eeeeee, 8e 88 [‌888‌]
Me MeMe Me(MM8)8, eeeeeeeeeeee, MeMM, 888°M, 88888 eee, 8.88e 88 [‌88‌]
Me MeMe MeMe8, eeeeeeeee, eeeeee, 88eee 88 [‌88‌]
Me MeMe=M 8. Me(MMe)8, eeee, eeeeeee, 888°M, 8e 88 [‌888‌]
8. MeMM, eeeeee, 8.8e
Me MeMe8 Me(MMe)8eM8M, MMM, eeeeeee, eeeeee, 8e, eeeeeeeeeeeeee 88 [‌888‌]
Me MeMe(MMe) Me(MMe)8eM8M, MMM, eeeeeee, eeeeee, 8e, eeeeeeeeeeeeee 88 [‌888‌]

Meeeeeeeeeee Meeeeeeeee

Meeeee(MM) Meeeeeeeeeeeee (8, M=Me8+); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeeeeeeee (8 eeeee) eee eeeeee eeeeee (8 eeeee) eee eeeeee eeee eeeeeeee. M eeeee eeeee eee eeeee eeeeeeee ee 888°M, eee eeee eeeeee eeeee ee 888°M eee eee eee eeeee ee ee eeeeeee ee 888°M. Me eee eeee eeeeeeeeeee ee eeeee 888°M, eee eeeeeeee eeeeeeeeeee eeeee ee eeeee eeeeeee eee ee eeeee eeeeeeee eeee ee eee eee eeee ee 88°M. Meeee 8eee, eee eeee eee eeeeee eee eeeeee eeee MeMM. Mee eeeeeeee eeeeeee eee eeeeeeeeee eeeeee eeee MeMM eee eeee eeeee. Mee eeeeeee eee eeeee ee eeeee M8MM8 (88 eeeee eee eeee ee eee eeeeeee) eee eeeee ee eeee eee eeee eee eeeeeeee eee eeeeee ee e eeee eeeeee eeee eee (888 eeeee eee eeee ee eeeeeee). Mee eeeeeeeeee eeee eeeeeeeeeee eee eeeeeee ee eeeeeeee eee 8e, eeeeeeeee ee eeeeeeeeee, eee eeeeee eeee eeeeeee M8M, eeee eeeeeee MeMM, eee eeeee ee 888°M; eeeee: 8888%.

Meeeee(MM) Meeeeeeeeeeeee (8, M=Me8+); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeeeeeeeeeeee (8.88e, 88eeee), MeMe (8.88e, 8.8eeee), eee MMM (8.88e, 88eeee) ee eeeeeeee (88eM) eee eeeeeeee eee 8e. Me eee eeeeeeee eeeeeeeee, e eeee eeeeee eee eeeeeeeeeeee. Me eeeeeee, eee eeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee ee MMe (8%), M8M, eee MeMM; eeeee: 8.8e (88%).

Meeeee(MM) Meeeeeeeeeeeee (8, M=Me8+); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeeeeeeee (8e, 88.8eeee) eee eeeee eeeeeeeee MeMe8 (8.8e, 8.8eeee) eee eeeeeeee ee eeeeeeeee (8eM) eeeee eee eeee eeeeeeeeee (88eee). Mee eeeeeeeee eeeee eee eeeeee eeee eeeeeee eee eee M8M, eee eeeeeeee eeeee ee eeee eee eeeee eeeeeeee; eeeee 8.88e (88%).

References