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31.6.1.1.2 Method 2: Reaction of Phenols with Arylboron Compounds

DOI: 10.1055/sos-SD-031-00413

Thomas, A. W.Science of Synthesis, (200731471.

The copper-mediated cross coupling of phenols with arylboronic acids at room temperature is a useful method for the synthesis of diaryl ethers. The original, nonoptimized conditions involve simply treating the phenol with an arylboronic acid in the presence of triethylamine and copper(II) acetate.[‌26‌] In each case, it is necessary to use an excess of the boronic acid reaction partner, and in most cases the yields are improved by using stoichiometric amounts of the copper catalyst. In an elaboration of this synthesis, the use of 5 equivalents of a base (either triethylamine or pyridine) was found to be optimal.[‌27‌] The presence of water formed by the dehydration of the arylboronic acid to the corresponding triarylboroxin causes competitive arylation and is detrimental to the isolated yield of the diaryl ether. Addition of molecular sieves to the reaction mixture eliminates the water, resulting in increased yields of the diaryl ether 6. These optimized conditions permit cross coupling of a wide range of both electron-deficient and electron-rich phenols with electron-deficient and electron-rich arylboronic acids in good to excellent yields at room temperature (Scheme 6).[‌27‌]

Meeeee 8 Meeeee-Meeeeeee Meeee Meeeeeee ee Meeeeee eeee Meeeeeeeeee Meeee[‌88‌]

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

Meee eeee ee eeeeeeee eee ee eeeeeee ee eee eeeee eeeeeeeee ee (M,M)-eeeeeeeeeeeee (88) (Meeeee 8),[‌88‌,‌88‌] eeeeeeeeeee eeeeeee,[‌88‌] eee eeeeeeeeeeee (88),[‌88‌] ee eeee ee ee eee eeeeeeeee ee eeeeeeeeeee eee eeeeeee eeeeeeeee.[‌88‌] Me eeee eeee eee eee eeee ee ee eeeeeeeee eeeeeeeeeeeeee eeeeeeee ee e eeeeee (e.e., 8) eeee e eeeeeee eeee (e.e., 8, ee eeee eee eeeeeeee eeeeeee 8).

Meeeee 8 Meeeeeeee ee Meeeeee Meeeeeee ee Meeee Meeeeeee ee Meeeeee eeee Meeeeeeeeee Meeee[‌88‌,‌88‌]

Mee eeeee eeeeeee eeee ee eee eee ee eeeeeeeeeeeeee eeeeeee ee eeeeee(MM) eeeeeee. Meeeeeeeeee eeeee eeeeeeee ee eeeeeeeeeee eeeeeee ee eeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeee eee eeeeee(MM) eeeeeee, ee eeeeeeeee eeeeeee eeeee ee eeee eeeeeeee.[‌88‌] Meeeeee, e eeeeeee eeeeee eee eee eeeeeeeee ee e eeee eeeee ee eeeeee eeeeee eee eee eee eeee eeeee eeeeeeeee. Meee eee eeeeeeee ee 8,8-ee-eeee-eeeeeeeeeee eeee 8-eeeeeeeeeeee eeee eee eeee eeeeeeee ee eee eeeeee (Meeeee 8);[‌88‌] ee eeeeeeeee eeeeee eee eeee eeeeeeeeee. Mee eee ee eeeeeeeee eeeeee ee ee eeeeeee eeeee e eeeeeeeeeee eeeee ee eee eeeeeee eeeeeee 88.[‌88‌] Meee eeee eeeee ee ee eeeeeee eee eeeeeeeee eeeeeeeee eeeeee eeee eeeee eeee eee eeeeeeeee ee eeeeee, eeeeeeee, ee eeeeee.[‌88‌] Mee eeeeeee, eeeeeeee e eeeeeeeee M-eeeeeeeee eeeeee eee eeeeeeeeee eeeee e eeeeee eeeeeee eeeee eeeeeeeeeeeee eeee ee eee eeee ee eeeeeeeee, ee eeee eeeeeeee 8% ee e eeeeeeeeeeeee eeeeee eeeee eeeeeee eeeee eeeeeeeee eeeeeeeeee.[‌88‌]

Meeeee 8 M Meeeee-Meeeeeeee Meeee-Meeeeeee Meeeeeee[‌88‌]

Meeeeeeeeee 8

Meeeeee Meeee (%) Mee
M8 88 [‌88‌]
MMMMM (8 eeeee), eee 88 [‌88‌]
eeeeeeee M-eeeee (8.8 eeeee), eee 8 [‌88‌]

Meeeeeee-eeee ee eeeeeeee-eeeeeeeee eeeeeeeeeee eeeee eee ee eeeeeee eeeeeeeee eeee eeeeeeeeeee eeeeee eeeeee ee e eeeee ee eeeeeeeee eee-eee eeeeeee eeeeeeeee eeeeee(MM) eeeeeee. Mee eeeeeee, e eeeeee ee eeeeeeeee eeeeee ee eeee eeee ee eeeeeeeeeee eeee 88 ee eeeeeeeee eeee e 88% eeeeeeee ee eeeeeeee eeeeeeee. Meeeeeee ee eeeeeeee 8-Å eeeeeeeee eeeeee, 8.8 eeeeeeeeeee ee eeeeee(MM) eeeeeee, eee 8 eeeeeeeeeee ee eeeeeeeeeeeee eeee eeeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeee eeeee 88 ee eeee ee eeeeeeeee eeeee (Meeeee 8).[‌88‌]

Meeeee 8 M Mee-Mee Meeeeeeee ee Meeeeeeeeee Meeeee Meeeee[‌88‌]

Me eeeeeeeeeee eeeeee eeee eeeeee eee eee ee eeeeeeee eeeeeeee eeee eeeee ee eeeeeeeeeeee eeeeeee eee eeee ee eeeeeeeee ee eee eeeeee eeee eeeeeeeeeee eeeee 88; eee eeeeeee eeeeeeeeeee eeeeee eeeeee 88 eee eeeeee ee eeee ee eeeeeeeee eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Me Meeeeeeeeee Mee-Mee Meeeeeeee ee Meeeeeeeeee Meeeee Meeeee[‌88‌]

M eeeeee ee eeeee eeeee eeeeeeee eee ee eeee ee eeee eee eeeeee eeeee 8, eeee eeeeeee eeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeee-Meeeeeee Meeeeeeee eeee Meeee Meeee Meeeeeee[‌88‌]

Meeeeeeeeee 88

Meeee Meeeeee Meeee (%) Mee
MeM(MM)8 8888 [‌88‌]
8888 [‌88‌]
88 [‌88‌]
88 [‌88‌]
88 [‌88‌]
88 [‌88‌]
88 [‌88‌]
8 [‌88‌]

Mee eeeeeeeeee ee eeeee eeeeee eeeee eeeeeeeee ee eeeeeeee eeeeeeeeeeeee ee eee eee ee e eeeeeeee eeeeeee 88 ee eeeeeeeeeeeeeeee (88). Mee eee eeeee eeeeeeee ee eeee eeeeeeee-8-ee eeeeee eeeee (88), eee eeeeeeee eeeeeeee ee eeeeee ee 88% eee eeeeeeeeeeeee eeee eee eeeeeeeeeeeeeeee (88), eee eee eeeee ee 88% eee eee eeeeeeee eeeeeee 88. Meeeeeeeeeeee, ee 8 eeeeeeeeee ee eeeeee eeeeeeeee ee eeeee ee e eeee, eee eeeeeeeeeeee eeeeeeee eeeeeeee eeee eeee eeeee eeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeee Meeeeeeeee ee Meeeee-Meeeeeee Meeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Meeeeeeeee Meeeeeeeee ee Meeee (%) Mee
MeM(MM)8 (8 eeeee), Me(MMe)8, MM8Me8, ee, 88e 8 [‌88‌]
MeM(MM)8 (8 eeeee), Me(MMe)8, MM8Me8, ee, 88e 88 [‌88‌]
88 (8.88 eeeee), Me(MMe)8 (8 eeeee), MM8Me8, ee, 88e 8 [‌88‌]
88 (8.88 eeeee), Me(MMe)8 (8 eeeee), Me8MM8 (8 eeeee), MM8Me8, ee, 88e 88 [‌88‌]
88 (8.88 eeeee), Me(MMe)8 (8 eeeee), MM8Me8, ee, 88e 88 [‌88‌]
88 (8.88 eeeee), Me(MMe)8 (8 eeeee), Me8MM8 (8 eeeee), MM8Me8, ee, 88e 88 [‌88‌]

Meeeeeeee, eeeeeee eeeeeeeee eee eeee eeeeeeeeeeeee ee eee eeeeee-eeeeeeee eeeee eeeeeeee (eee Meeeee 88). Me eeeeeee eeeeeeee eeee eeeeeeee eeee eee eeeeeeeeee ee eeeeeee eeeeeeeee ee ee eee eeee ee e eeeeee ee eeeeeeeeeee eeeee, eeeeeee eeeeeeeeeeeeeeeeeee eeee e eeeeeeeeeee-eeeeeeeeeee eeeeeee eeee. Meee ee eeeeeeeee eeeeeeeeee-eeeeeeeeee-eeeee eeeeeeee eee eeee ee eeeeeee ee e eeeeee-eeeeeeee eeeee eeeeeeee ee eee eeeeeee eeeeeeeeeeee 88 ee eeee eee eeeeeeeee eeeeeee 88 eee eee eeeeee eeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Me Meeeeeeee Meeeeeeeee-Meeeeeeeee-Meeee Meeeeeee eee eee Meeee Meeeeeee ee e Meeeeee Meeeeeeeeeee[‌88‌]

M eeee eee eeeeeeeeeee eeeeeee eeeeeeee eeeeeeeee eee eeeee eeeeeeee ee eee- eee eeeeeeee-eeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeeee eeeee eeee eeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee e eeeeee(MM) eeee eeeeee ee eeeeeeeeeee eeeeeeeee eeee eeeeeeeeeee eeeee ee eeeeee eee eee eeeeeeeee ee e eeee eeeee ee eeeeee eeeeee 88 (Meeeee 88).[‌88‌] Meeeeeee ee eee eeee eeee ee eeee eee eeeee, eee eee eeeeee eeeeeeee eeee 88eee% ee eeeeee(MM) eeeeeee eeeeeeeeeee eee eeeeeeeeee e eeeeeeeee eeeeee (88eee%) ee 8-(eeeeeeeeeeeee)eeeeeeee ee ee eeeeeeeeee eeeeeeee; eeee eee eeeee ee e eeeeee eeeeee. Mee eeeeeeeee eeeeeeeeee eeee eeee ee eee eee ee eeeeeeeee eeeeee, eeeeeeeee eeeeee, eee eeeeeeeeeeeeeee eeeeeee.

Meeeee 88 Meeeee-Meeeeeeee Meeee Meeeeeee ee Meeeeeeee Meeeeeeeeeeeeeeeeeeee Meeee eeee Meeeeee[‌88‌]

Meeeeeeeeeeeee ee eeeeee [eeee eeeeee(MM) eeeeeee] ee e Meee eeeee eeeee e eee eeeeee eeeeeee 88 eeee ee eeeeeee ee eeeeeeeeeee eeeeeeeee eee eeeee eeeeeeee ee eeeeeee eeee eeeeeeeeeee eeeee ee eeee eeeeee eeeeee 88 (Meeeee 88). Mee eeeeeeeee eeeeee eeeeeee ee eee eeeeee eee eee ee eeeeeeee eeeeeee eeeeeeeeeee eeee ee eeeeeeee.[‌88‌]

Meeeee 88 Meeee Meeeeeee ee Meeeeeeeeee Meeee eee Meeeeee eeee e Meeee-Meeee Meeeee Meeeeeee[‌88‌]

Mee ee eee eeee eeeeeeeeeee eeeeeeeeeeeeeee eeeeee eee eeee ee eeeeee eeeee eeeeeeeee ee eee eeeeeeeee ee e eeeeee eeeee eeee eeeeee e eeeeeeeeeee eeeeeeeee ee ee eeeeeeeeeeeeee eeeeeee.[‌8‌,‌8‌] Me eeeeeeee eeee-eeeeeeee eeeeeee, ee ee eeeeeeee ee eeeeee eeeeeeeeeeeee eeeeee eeeeee (8888%) ee e eeeee ee eeeeeee eeeeee eeeee eeeeeeeeee eeeeeeeeeee eeeeee 88 eee 88 eeeeeee ee eeeeeeeeeeeeee eeeeee-eeeeeeee eeeeeeee ee e eeeeee eeeee eeee e eeeeeee eeee eeeee (Meeeee 88).[‌88‌] Me eeee eeee, eee eeeeeee eeeeeeeee eeeeeeee eeeeeeeeeeeee ee e eeee eeeeeee ee eeeeee; eeeeeeeeeeee, eee eeeeeee eeeeeeeee eee eee eeee eeeeeeeeee eee eee eeeeeeeeeeeeee eeeeeee, ee eeeeeeee ee eee eeeeeeeeeeeeee eeeeeee ee eeee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeee ee ee Meeeeeeeeeeeee Meeeee-Meeeeeee Meeeeeee[‌88‌]

M eeeeeee eeeeeeee eeee 8-(eeeeeeeeeeeee)eeeeeeee ee eee eeeeeeee eeeeee eee eeeeeeeee eeeeeeeeeeee ee eee eeeeeeeeee eeee ee M,M-eeeeeeeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeee ee eee eeeeeeee (e.e., eeeeeeeeee ee 88 eeee 88, Meeeee 88).[‌88‌] Mee eee ee eeeee eeeeee eeeeeee ee eeeee [eeee ee eeeeeeee, eeeeeeeeee, M,M-eeeeeeeeeeeeeeeeeeeee (Müeee'e eeee), 8,8-eeeeeeeeeeeeeeee, 8,8-eeeeeeeeee, 8,88-eeeeeeeeeeeeee, ee 8-eeeeeeeeeeeeee] eeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeeeeee eeeeeeee ee eee eeeee eeeeeee eee eeee eeeeee eeeeee ee eee eeeeee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeeeee ee ee M,M-Meeeeeeeeeeeeeeeee Meeeee[‌88‌]

Mee eeeee eeeeeeeeeeeeeee eeeee eeeeeeeee ee eeeeeeeeeeee M, ee eeee-MMM eeeee, eeeeeeee ee eeeeeeeeeeeeee eeeeee-eeeeeeee eeeee eeeeeeee ee e eeeeeee eeee eeee e eeeeee ee eee eeeeeeeeeee ee e eee eeeeeeee eeeeeeeeeeee 88 (Meeeee 88).[‌88‌] Me eeee eeeeeeee, 88 eeeeeeeeeee ee eeeeeeee eee eeeee ee eee eeeeeee; eeee ee eeeeeee ee eeeeee ee eee ee eeee eeeeeeeee ee eee eeeee eeeeeeee eeeee eee ee eeeeeeee eee eeeeeeeeee ee eee eeeeee eeeeeee. Me eee eeeeeee ee eeeeeeee, eee eeeeeeee eeeeeeee eeee e eee eeeeeeeeee (8888%).

Meeeee 88 Mee Meeeeeee ee eee Meeee Meeeeeeee ee Meeeeeeeeeee M[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meee 8-eeee-Meeeeeeee Meeeee 8; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-eeee-eeeeeeeeeee (8 eeeee), ee eeeeeeeeeee eeee (8 eeeee), Me(MMe)8 (8 eeeee), eee eeeeeeee 8-Å eeeeeeeee eeeeee eee eeeeeee eeee MM8Me8 ee 8.8M eeeeeeee ee eee 8,8-ee-eeee-eeeeeeeeeee. Me8M (8.88 eeeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee eee 88e. Mee eeeee eeeeeee eee eeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8888%.

Meeeee (8M)-8-{8-[8-(Meeeeeeee)-8-{(8M)-8-(eeeeeeeee)-8-[(eeee-eeeeeeeeeeeeee)eeeee]-8-eeeeeeeee}eeeeeee]eeeeee}-8-{[(eeeeeeeee)eeeeeeee]eeeee}eeeeeeeeee (8):[‌88‌]

Mee eeeeeee eeee 8 (8.88e, 8.888eeee), Me(MMe)8 (8.888e, 8.88eeee), eeeeeeee (8.888eM, 8.888eeee), eee eeeeeeee 8-Å eeeeeeeee eeeeee eeee eeeee ee e eeee ee eee eeeee 8 (8.88e, 8.888eeee) ee MM8Me8 (8.8eM), eee eee eeeeeee eee eeeeeee eee 88e eeeee ee eeeeeee eeeeeeeeee. Mee eeeeeee eee eeee eeeeeeee, eeeeeee eeee MeMMe, eee eeeeee eeee 8M MeMM eee eeeee. Mee eeee eee eeeee (MeMM8) eee eeeeeeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/Me8M 8:8) ee eeee e eeeee eee; eeeee: 8.888e (88%).

Meeeeeeeeee Meeeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee ee eeeeeeeeeee eeee 88 (8eeee, 8 eeeee) ee MM8Me8 (88eM) eee 88% ee M8M8 (8.88 eeeee) eee eeeeeee ee ee eee eeeeeee eeeee. Meeeeeee 8-Å eeeeeeeee eeeeee, Me(MMe)8 (8.8eeee, 8.8 eeeee), eee Me8M (8 eeeee) eeee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeee eeeeeeeee. Mee eeeee eeeeeee eee eeee eeeeeeee eeee eeeeee eee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8888%.

Meeeeeeeeee Meeeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me eeeeeeeeeee eeee 88 (8eeee), Me(MMe)8 (8eeee, 8 eeeee), eee Me8M (8 eeeee) eeee eeeeeeeee ee eeeee MeMM/MM8Me8 (8:8; 88eM). M8M (88 eeeee) eee eeeee eee eee eeeeeee eee eeeeeee eeeeeeeeee ee ee eee 8e, eeee eeeeeeee, eee eeeeee eeee eee. ee MeMMM8 eee eeeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:8); eeeee: 8888%.

Meeeeeee-8-ee Meeeee Meeee (88); Meeeeee Meeeeeeee:[‌88‌]

Me(MMe)8 (8.88e, 8.88eeee) eee eeeeeee ee ee ee eee MM8Me8 eee 88eee. Meeeeeeeeeeeeeeeeeeeeeee eeeeeee 88 (8.8e, 8.88eeee), eeeeeeee-8-ee (8.88e, 8.88eeee), eee eeeeeeee (8.8eM, 8.8eeee) eeee eeeee eee eee eeeeeee eee eeeeeee ee ee eee 88e. Mee eeeeeee eee eeee eeeeee eeee 8M ee MM8MMe (8×88eM), eee eee eeeeeee eeeeee eeee eeeeeeeee eeee MeMMe (8×88eM). Mee eeeeeee eeeeee eeee eeee eeeeeeee, eeeeee eeee eeeee (8×88eM), eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeee eee eeee eeeeee eeeeeee e eeeee eeee ee eeeeeee eeee MM8Me8 eee eee eeeeeeee eee eeeeeeeeeeee ee eeee e eeeee eeeee; eeeee 8.88e (88%); ee 8888°M.

Meeeee 8-Meeee Meeee (88, Me8=8-Mee); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeeee (8.888e, 8eeee), Me(MMe)8M8M (8.88e, 8.8eeee), MMMM (8.88e, 8.8eeee), eee eeeeeeee 8-Å eeeeeeeee eeeeee (8.8e) ee MM8Me8 (88eM) eee eeeeeee eee 8eee ee ee. 8-MeeMM (8eeee) eee eeeee, eee eeeee eee eeeeee eeee e eeeeee eeeeee, eee eee eeeeeee eee eeeeeee eeeee ee eeeeeeeeee ee M8 eeeeeeeee eeee ee eeeeee eeee eeeeeeeee ee e eeeeeeee. Meeee 88e, eee eeeee eeeeeee eee eeeeeeee eeeeeee e eeee ee Meeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/eeeeeee 8:8) eeee e eeeee eee; eeeee: 88%.

Meee 8-Meeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee e eeeeee (8.88eeee), eeeeeeeee eeeeeeee 88 (8.88e, 8.8eeee·e8, 8.88eeee), 8-eeeeeeeeeeee eeee (8eeee), eeeeeeee 8-Å eeeeeeeee eeeeee, eee Me8M (8.88eeee) ee MM8Me8 (8eM) eee eeeeeeee eeeeeeeeee eee 88e ee eee eeeeeeee ee eee. Mee eeeeeee eee eeeeeee eeee MeMM (8eM) eee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 8888%.

Meeeee (8M,88M)-88-[(eeee-Meeeeeeeeeeeee)eeeee]-8-eeeeeee-88-eee-8-eee-88-eeeeeeeeeee[88.8.8.88,8]eeeeeeee-8(88),8(88),8,8,88,88-eeeeeee-8-eeeeeeeeeee (88):[‌88‌]

MMMM (88ee, 8.888eeee) eee eeeeeeee 8-Å eeeeeeeee eeeeee (888ee) eeee eeeee ee e eeee ee eee eeeeeeeee 88 (88.8ee, 8.8888eeee) ee MM8Me8 (8.8eM), eee eee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88eee. Me(MMe)8 (88.8ee, 8.8888eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee eee e eeeeeee 88e. Mee eeeeeee eee eeeeeeee eee eee eeeeeeee eee eeeeeee eeee MMMe8 (88eM). Mee eeeeeee eeeeeee eee eeeeee eeee ee MMMM8 (88eM) eee eeeee (88eM), eeee eeeee (MeMM8), eee eeeeeeee. Mee eeeeeee eee eeeeeeeeee eee eee eeee eeeeeee eee eeeeeeee ee MMMM (MMM, MeMM/M8M 88:8) ee eeee e eeeee eeeee; eeeee: 88.8ee (88%); [α]M88 +88 (e 8.88, MMMe8).

References


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