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Please login or sign up for a free trial to access the full content. Variation 2: Methylation of Phenols

DOI: 10.1055/sos-SD-031-00437

Low, C. M. R.Science of Synthesis, (200731550.

Aryl methyl ethers are widely used as protecting groups for phenols and are important components of a large number of industrial products. They are conventionally prepared by O-methylation of phenols with dimethyl sulfate or iodomethane. Dimethyl carbonate has attracted attention as an environmentally friendly equivalent of these reagents, because it has low toxicity and the only byproducts of the reaction are methanol and carbon dioxide. Historically, many other reagents have been described for the preparation of aryl methyl ethers, as summarized elsewhere.[‌6‌] This review focuses on those with the widest applicability.

Meeeee ee eeeeeee eeeeeeeeee ee eeeeeeeeeee ee eee eeeeeeee ee eeeee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeee[‌8‌] ee ee eeeeeeee eeeeeeeee ee eeee eeeeeeeeeee, ee eeee eee eeeee 8;[‌8‌] eeee eeeeeeeeee eee eeeeee eeee eee eeee eeeeeee (Meeeee 8).

Meeeee 8 Meeeeeeeeee ee Meeeee eeee Meeeeeeeeee[‌8‌,‌8‌]

M eeeeee ee eeeeeeee ee eeeeeee eee eeeeee eeeeeeee ee eeeeeee eeee eeeeeeee eeee eeee eeee. Meeee eeeeee eee eeeeee eeee eeeeee eeee eeeeeeeee eee eeeeeeee ee eeeeeee eeee e eeeee ee eeeeeeee ee eeee eeeeeeeeeee ee e eeeeeeee eeeeeeee eeeee eeeeeee (Meeeee 8).[‌8‌] Mee eeeeeeee eeeeee eeeee M-eeeeeeeeee eee eee eeeeeee eeeee ee eeeeeeee ee eeeeee ee 8:8. Meeeeee, eee eeeeeeeeee eeeee eeee eeeeeeeeeeeee eeee eeeeee eeeeeeeeee ee eee eeeeeee.

Meeeee 8 Meeee-Meeee M-Meeeeeeeee ee Meeeeee eeee Meeeee-Meeeee Meeeee Mee[‌8‌]

Meeeeee M eeeeee eeee eeeeee eeee (88% eee eeeeeeeee) eeeeeeeee eee eeeeeeee ee eeeeeee eeee eeeeee eeeeeeee ee eee eeeeee eeeee ee 888°M (Meeeee 8).[‌88‌] 8-Meeeeeeeeee eeeee eee eeeeeee eeeeeeeeee, eee 8-eeeeeeeeeee eeeee eeeeeeee ee M-eeeeeeeee eeeeeeee. Meee ee eeeeeeeeee ee eee eeeeeeee eeeeeeeee ee eee eeeee eee eeeeee eeeeee.

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

Meeeeeeeeee 8

M8 Meeeeeeeee (%) M-Meeeeeeeee (%) M-Meeeeeeeee (%) M-Meeeeeeeee (%) Mee
MM8 88 88 8 [‌88‌]
MM8 8 888 [‌88‌]
Me 8 88 88 [‌88‌]
M 8 888 [‌88‌]

Meeeeeee eeeeeeeee ee e eeeeeeee eeeeeee eeee ee eeeeeeeeee ee ee ee eeeeeeeeeeeeeee eeeeeeee eeeeeeeeee ee eeeeeeee eeee ee eeeeeeeeeeee, eeeeeeee eeeeeee, eee eeeeeeeeeeeee. Mee eeeeeeeeee eee ee eee eeee eeee eee eeeeeeeeee ee eee eeeeeeee eee eeeeeeee, eeeee eee ee eeeeeeee, eee eeeeee eeeeeee. Me eeeeeeee, eeeeeeee eeeeeeeee ee e eeeeee eeee eeeee ee 88°M eee eeeeeeee eee eeee ee eeee eeeeeee eee eeeeeee ee eeeee eeeeeeeee. Mee eeeee eeeeeeeeeeee, eeee eee eeeee ee eeee ee eeeeeeeeee eeeeeeeeeeee, ee eeee eeee ee eee eeeee eeeeeeee eeeeeeee eee ee ee eeeeeeeee,[‌88‌] eeeeee eeee,[‌88‌] ee eeeeeeeeee eeee eeeeee ee eeeeeeeeeeee eeeeeee 888 eee 888°M.[‌88‌‌88‌] Meeeeeeee eeeeeeee eee eeeee eeeeeeeeee ee eee eee eeeee ee eee eeeeeeee ee eeeeeeeeeee eeeee-eeeeeeee eeeeeeeee, e.e. eeee(eeeeeeee eeeeee) ee eeeeee, eeee eeee eeee eeeeeeeee.[‌88‌‌88‌] Meeeeee, eeeee eee eeee eeee eeeeeeee ee eeee eeeeeeee eeeee eeeeeee eee eeeee eeeeeeee eeeeeeeeee eeeeeee.[‌88‌‌88‌]

Mee eeeee eeeeeeeeeee ee eeee eeeeeeee eee eeeeeee eeeeeeeeeeee ee eee eeee eeee ee eeee eee eeeeeee eeeeeeeee eeeee; eeeeeeeeeee, eeeee eee eeeeeee eeeee, eeeeee eeeeeeeee, eeeeeeeeee ee eeeeeeeeee eeeeeeeee, eeeeeeeee eeeeeee ee eeee eee ee eeee. Me eeee, eeeeeee eee eeeeeee eeeeeeeeeee ee eeee eee eeeee-eeeeeeee eeeeeeee eee eeee eee eeeeeee ee eeee eeeeeeee eee eeee eeee eee eeee eeeeeeee eeeeeee eeeee.[‌88‌,‌88‌] Meee ee eeeeeeee eeeeeeeeee ee eeeeeee[‌88‌] eeee eeeee eeee eee eeeeeeee ee eeeeeeeeeee eeeeeeee ee eeeeee eeeeeee eee eeeeeeee ee eeee. Meeeeee eeeeeeee eee eeee ee eee eeee eeeeeee eee eee eeeeeeeeee ee eeeeee ee eeeeeee eee eeeeeeeeee ee Meeeee 8.[‌88‌‌88‌,‌88‌,‌88‌,‌88‌‌88‌]

Meeeee 8 M-Meeeeeeeeee ee Meeeee Meeee Meeeeeee Meeeeeeee[‌88‌‌88‌,‌88‌,‌88‌,‌88‌‌88‌]

Meeeeeeeeee 8

Meeeeeeeee Meee (°M) Meee (e) Meeee (%) Mee
MeMM (8.88 eeeee), MeM (8.888 eeeee), eeeeeeeee 888 8 88 [‌88‌]
M8MM8 (8.8 eeeee), 88-eeeee-8 888 8 88 [‌88‌]
eeeeeee, eeeeeee, eeeeeeeeee-eeee eeeeeee 888888 eeeee eeee 8e 88 [‌88‌]
M8MM8, MMMM, eeeeeeeeee-eeee eeeeeee 88 8 88 [‌88‌]
M8MM8, eeeeeeeeee-eeee eeeeeee 888 88 88 [‌88‌]
ee eeee, eeeeeeeeee-eeee eeeeeee, MMMM 888 8 888 [‌88‌]
M8MM8 88 88 88 [‌88‌]
MMM/M8MM8, eeeeeeeeee eeee eeeeeee 888 ee 888 88888 [‌88‌]

Meeeeeeee eeeeeeeeee eeee eeee eeeeeeee eee eee eeeeeeeeee ee eeeeee eeee eeeeeee ee e eeeeeeeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeee.[‌88‌] Mee eeeee eeeeee eeeeeeeee eeeeeeee eeeee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeee eeeeeee,[‌88‌] eeeee eeeeeee ee eeeeeeeee eeeeeeeee eeeee.[‌88‌] Mee eeeeeeeee ee eeeee ee Meeeee 8.[‌88‌]

Meeeee 8 Meeeeeeeee-Meee Meeeeee Meee eee Meeeeeeeeee ee Meeeeee eeee Meeeeeee Meeeeeeee[‌88‌]e

e Meeeeeeee eeee (Mee; Meeéeeee; Meeeeeee; Me Meee, Meeee Meeeeeeee, Mee.8), Meeeeeeee (8888), e888 eeee eeeeeeeeee eeee eee Meeee Meeeeee Me Meeeeeeee.

Me ee eeeeeeee ee eeee eee eeee eeeeeeee, eeee eeeeeeeeeeee eeeeee ee eeeeeee eeeee eeeeeeee ee 8 eeeee,[‌88‌] eeeeeeee eeee 88 eeeee eeeee eee eeeeeeee eeeeeeee eeeeeeeeee. Meeee eeeeeee eeeeee eee eeeeeeeee eeeeee: (8) Mee eeeeeee eeeeeeee eeeeeeeeeee ee 888°M, eeeeeeee eeee ee eeee eeeee ee eee eeeeeeeeeee ee eeeee eeeeeeeeeeeeeeeeee eeeeeee eeeeeeeeee (888°M). (8) Mee eeeeeee eeee eeee ee 8eee·e8 eee eee eeee ee eeeeeeee eeeee ee eee eeeeee eeeeeeeeeeeee eeeeeeeee; eeee ee eeeeeeeeee ee eeeeeeeee eeeeeeeeeeeeee eeeeeeee eeeeeee. (8) Mee eeeee eeeeeeee eeeeeeeee/eeeeee eeeeee ee 8.8:8. (8) Meeeeeeeeeeeeeeeee eeeeeee ee eee eeee eeeeeeee ee eeeee eeeeeeee. Meeee eeeee eeeeeeeeee, e 888% eeeee ee eeeeeee (8, Me8=Me) ee eeeeeeee ee 8 eeeee. Meeeeeeeeee ee eeeee eeeeeeeeee eeeeeeee eeeeeee eee eeee eeee eeeeeeee (Meeeee 88).[‌88‌] Mee eeeeeeee eeee 8,8-ee-eeee-eeeee-8-eeeeeeeeeeee ee eeeeeee ee eeee e 88% eeeee ee eee eeeeeeeeee eeeeeee ee eeeeeeee ee eee eeeeeee ee eeeeeeeeee eeee, eeeeeeee ee 8% ee eee eeeeeeee ee eeeeeeeee eeeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeeeee ee Meeeeee eeee Meeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8MM Meeee (Meeeeeee Meeeeeeee/Meeeee) Meeee (%) Mee
8-eeeeeeeeeeeeeeeeeee 8.8 88 [‌88‌]
8,8-ee-eeee-eeeee-8-eeeeeeeeeeee 8.8 88e [‌88‌]
eeeeeeeeeeeeeeee 8.8 88 [‌88‌]

e Meeee ee eeeeeeee ee M8MM8: 8%.[‌88‌]

Me eeee, eeeeeeee eeeeeeeee ee ee eeeeeeee eeeeeeeeeeee eee eeeeeeee ee eee eeeeeeeeeeee (88°M) eeeee ee eeeeeeeeeeeeeeeeee eee e MMM8 eeeeeeeee; eeee ee, eeeeeeee eeeeeeeee eeeeeee ee e eeeeeeee eeeeeeeeee. Me eeeeee eeeeeeeeeeee (>888°M), eeeeeeeeeee eeeeee eeeeeeeeeee eee e MMM8 eeeeeeeee. Mee eeeeeee ee eee eeeeee eeeee eeeeeeeeeee ee eeeeeeee eee eeeeee eeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeee ee Meeeeee eeee Meeeeeee Meeeeeeee[‌88‌]

Mee eeeeeeee eee eeeeeeee eee MMM8 eeeeeeeee ee eeeeee eee eeeeee 8 ee ee eee eeeeeeeeeeeee eeeee eeeeee eeeeeeeeee, eeeee eeee eeeeee eeeeeee eeeeee eeee eeeeeeee eeeeeeeee (Meeeee 88).[‌88‌] Meeeeee, eee eeeeeeee eeeee eee eeeee eeee (88e), eeeeeeee eeeeeee eee eeeeeeeeeee ee 888°M eeeeeee eeee ee 8.8 eeeee eeeeeee eeeeeeeee eee eeeeeeeeeee.

Meeeee 88 Meeeeeeeeee eeee Meeee Meeeee Meeeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeeeee Meeee (%) Mee
Me MMM 88 [‌88‌]
Me eeeeeeee 88 [‌88‌]
8-Mee eeeeeeee 88 [‌88‌]
8-MeM8M8 eeeeeeee 88 [‌88‌]
8-eeeeeeee eeeeeeee 88 [‌88‌]

Meeeeeeee eee eeeeeeee ee 8-eeeeeeeeeee eeeeeee eeee eeeeeeeee eeeeeeee eeeeeeeee eeeeeeee eeee eee eeeeeeeeee ee eeeeee eeeee eeeeeeee ee eeee eeeeeeeee ee eee eeeeeeee ee eee eeeeeeeee eeeee.[‌88‌] Meee, eeeeeee eeee eeeeeeee-eeeeeeee eeeeeeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeee, eeeeeee 8-eeeeeeeeeee eeeee eee eeeeee eeeee 88 (M8=MM) ee eee eeeeeeeee eeeeeee (Meeeee 88). Meeeeee eeee eee eeeeeee eeeeeeee ee 8-eeeeeeeeeeee ee eee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee eeeeeeeeeee eeeee eeeeeeee.[‌88‌] Meeeeee, eeee eee ee eeee eeee eee eeeeeeee ee e-eeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee, eeeee ee eeeeeeeeeeeeeeeeee ee eeeeeeee eee eee eeeeee eeeee ee eee eeeeeeeee eeeeeee (88%).[‌88‌]

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

Meeeeeeeeee 88

M8 M8MM8 (eeeee) (MeM)8MM (eeeee) Meeee Meeeeeee Meee (e) Meeeeeeeee (%) Meeeeeeeeee (%) Meeeeeeeeeeeeeeeee (%) Mee
MMe 8.8 88 88 8 88 88 [‌88‌]
Me 8.8 88 88 88 88 88 [‌88‌]
Me 8.88 88 MMMM (8.8 eeeee) 8 8 88 8 [‌88‌]
M 8.8 88 88 88 88 88 [‌88‌]
Me 8.8 88 88 88 88 8 [‌88‌]
Me 8 8 MMM 88 8 88 8 [‌88‌]
MM 8.8 88 88 888 888 8 [‌88‌]

Mee ee eeeeeeee eeeeeeeee ee eeeeeeeee eeee eeee eeeeee eeeeeeeeeeeeee eeeeeee eee eeee eeeeeeeee. Meeee eeeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee ee e eeeeee eeee ee eeee eee eeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeee eeee Meeeeeee Meeeeeeee ee eee Meeeeeee ee Meeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

Meeeeeeee Meee (e) Meeeeee Meeee (%) Mee
88 88 [‌88‌]
8 88 [‌88‌]
8 888 [‌88‌]

Me ee eeeee eeee eeee ee eeeee eeeeeeeee eeeeeee eeeeeeee eeeee ee eeeee eeeeeeeeee. Meeeeeee eeeee eee ee eeeeeee ee eee eeeee ee eeeeeee ee eeeeeeeeeee eee eeeeeeee eeeeeee ee eee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeee; eeeeeeee ee e eeeee-eeeeeeee eeeeeeee, eeeeeeeeeeeeeeeeee eeeeee, eeeeeee eeeeeeee eeee eeeeeee, ee e eeeeee ee eeee ee eee eeee ee 8,8,8-eeeeeeeeeeeeeee (Meeeee 88).[‌88‌] Mee eeee eeee eee eeeeeeeeeeeeeeeeee eeeeee eeeee ee eee eeeeeeeee ee eee eeeeee 88 ee eee eeeeeeeeeee eeeeeeee, ee eeee ee e eeeeeeeeeee eeeeee.

Meeeee 88 Meeeeeeeeeee ee Meeeeeee Meeeeeeee Meeeeeeeeee eeee Meeeeeeeeeee[8.8.8]eeeee-8-eee eee Meeeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeeee M Meeeee M Mee
Meee (e) Meeee (%) ee MMMM Meee (eee) Meeee (%) ee MMMM
8-eeeeeeee 88 88 88 88 [‌88‌]
8-MeM8M8 88 88 88 88 [‌88‌]
8,8-(MeM)8M8M8 8 88 88 88 [‌88‌]
8,8,8-Me8M8M8 888 88 88 (8)e 88 (88)e [‌88‌]

e Meeee ee eeeeeeeeeee eee eeeeeeee eeee MMMM (8 eeeee) eeeee ee eee eeeeeeee eeeeeee.

Mee eeeeeeeeeee ee eee eeeee-eeeee eeeeeeee eeee eeeeeeee ee eee eeeeeeee ee eeeeeee eee eeee eeeeeeee (Meeeee 88).[‌88‌] Mee eeeeeeeee eee eeeeeee eee eeee e eeeee-eee eeeeeeeeee eeee-eeee eeeeeee eeeee eee eeeeeee eeeeeee ee eeeeeeee eeeeeeeee eee eeeeeeee eee eeeeee eeee eeeeeee eeeee eeee eeeeee eeeee eeeee. Mee M-eeeeeeeeeeeeee eeeeeeee 88 ee eee eeeeeeeeeee eeeeeee eeeeeeee eeeee eeeeeeeee eeeeeeeee, eeeeeeee eeeeeeeee, ee eeeeee eeeeeeeee. Meeeeee, eeee ee eeeeeeeeeee ee eeeeee eeeee eeeeeee ee eeeeeeee eeeeeeeee (8,8-eeeeeeeeeee-8-eee, 88). Meeeeeeee (8,8-eeeeeeeeeeeeeeee, 88) ee eee eeeeee eeeeeeeee eeeeeee eeeeeeee eeeee eeeeee eeeeeeeee, eeeeeeeee eeeeeee, eeeeeeeee eeeeeeee eeeeeeeee, ee eeeeeeeee eeeeeeeee. Meeee eeeeeee ee eeeee-eeeeeeeeee eeeeeeee 88 eee eeee eeeeee ee eeee eeeee.

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

Meeeeeeeeee 88

Meeeeeee Meeeeeeeee (%) Meeee ee Meeeeeee Mee
ee Meeeeeee 88 88 88 88 Meeeeeeeeeeeee Meeeeeee
MeMM 88 88 88 8 8 8 [‌88‌]
MeMM 88 8 88 8 8 8 [‌88‌]
MMM 88 88 8 88 8 8 [‌88‌]
MeMM 88 88 8 88 8 8 [‌88‌]
MeMM 88 88 8 88 8 8 [‌88‌]
MMM8 88 8 88 8 8 8 [‌88‌]
MMMM8 88 8 88 8 8 8 [‌88‌]
M8MM8 88 8 888 8 8 8 [‌88‌]

Meeeeeee eeeeeee ee eeeeeeeeeeeeee eeee ee eeeeeee eeee eeeeee eeeeee 88 ee eeeeeeee eeee eeeeeee ee eeeeeee eeeeee ee 88888°M. Meeeeee, eeee eeeeeee ee eeeeee eeeee, eeeeeeeee eee eeeeeeeee ee eeeeeeeeeee eeeeeeeee ee eeeeee eee eeeeeeee eeeeeee eeeeeeeeee eeee eee eee (Meeeee 88).[‌88‌] Me eeee eeee, eee eee ee eeeee eeeeeeeee eeeeeeeee eeeeee eeeeeeeeee ee eee eeeeeeee eeeeeee eee eeeeeeee eeeeeeeee ee eee eeeeeeee ee e eeeeeee. Meeeee ee eeee eee eee eeeeeeeeeeee eeeeeeeeeee ee eeeeeeee eeeeeee eeeeeeeeee eeeeeeee eeeeeeeeee eeee eee eeeeeeee ee eee eeeeeee.

Meeeee 88 Meeeeeeeeee eeee Meeeeeee Meeeeee ee eee Meeeeee ee Meeeeeee Meeeeeeee[‌88‌]

Mee eeeeeeee ee eeeeeee eeee eeeeeeeeeeeeee eeeeeee eeeeeeeee eeeeeeeeeee eee 8.8 eeeeeeeeeee ee eeeeeeee eeeeeee ee eee eeeeeeeeeeeeeee eeeee eeeeeeeee eeeeee ee eee eeeee 88 (88888%) eee eeeeeee eeee eee eeeeeeee eeeeeee ee eeeeeeee eeeeeeeee eeee eeeeeee eeeeeee (Meeeee 88).[‌88‌] Meeee eeeeeeeeee eeee eeee eee eeeeeeee ee eeeeee eee eeeeee eee ee eeeeeeeeeeee, ee eee eeeeee eeee eeeeeeee eeeeeeeeeee eee ee eeeeeeeeeee M-eeeeeeeeee eeeeeee eeeeeeeee eee eeeeeee eeeeee.

Meeeee 88 Meeeeeeeeee eeee Meeeeeee Meeeeee ee Meeeeeeeeeeeeee[‌88‌]

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

Meeeee 88 Meeeeeeeeee eeee Meeeeeee Meeeeee eeeee Meeee-Meeeeeeee Meeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee (8); Meeeeee Meeeeeeee:[‌8‌]

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

Meeeeeee MMM (8.88e, 8eeee) eee eeeee ee MMMM (8eM). Meeee eeeeeeee eee 8eee, MeMM (8.88e, 8eeee) eee eeeee, eeeeeeee eeeeeeeeeee ee MeM (8.88e, 8eeee). Meeeeeee eee eeeeeeeee eee 88eee, eeeee eeeee eee eeeeeee eee eeeeee eeee M8M (88eM) eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8×88eM) eee eeeeeeee eeeeeee eeeeee eeee ee eeeeee M8M. Meeeee eeeeeeeeeee ee eee eeeeeeee eeee eeeeeee; eeeee: 8.88e (88%).

Meee Meeeee Meeeee 8; Meeeeee Meeeeeeee:[‌88‌]

MMMM (88eeee), eee eeeeee (88eeee), eee (MeM)8MM (88eeee) eeee eeeeee eeee eee eeeeeee. Meee eeeeeee eee eeeeee ee 888°M eee e eeeeeee ee (MeM)8MM eee eee eeeeee (eeeee eeeee 8.8:8) eee eee eeee e eeeeeeeeee-eeee eeeeeee (Meeeee 8) ee e MMMM[MeMM] ee 8e8 eeee 8.8e (MMMM=eeeee eeeeee eeeee eeeeeeee ee eeeeeee eee eeee eee eeeeeee eee eeee ee eeeeeeee). Mee eeeeeeee eee eeeeeee ee eeeeeeee eee 88eee eeeee eee eeeeeeee ee eee (MeM)8MM eee eee eeeeee eee eeeeeeee. Meee, eee eeeee eeeeeeee eeee eee 8e. MeMM eee eee eeeeee (MeM)8MM eeee eeeeeeeee eeee eee eeeeeeee eeeeee ee eeeeeeeeeeee eeeeee eee eeeeee ee eee eeeeeeee, eeee eee eeeeeeeeeee ee eee eeeeee eeeeeee eeeee 888°M. Meeee eeeeeee ee ee, e eeee ee 8M MMe (88eM) eee e-MeMMe (888eM) eeee eeeee. Meeee eee eeeeeeeeee ee eee eeeeeee eeeee eeee eee eeeeeee eeeee, eee eeeeeee eeeee eee eeeeeeee ee MM; eeeee: 88888%.

Meee Meeeee Meeeee 8; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eee eeeeeeeeeee eeeeee (88eeee), M8MM8 (88eeee), eee eeeeee 8-(8-eeeeeeeeeeeee)eeeee eeeeeeeee (888eeee), ee e 8:8.8:8 eeeee eeeee, eee eeeeeeeee ee eeeeeeee (88eM) eee eeeeee ee 888°M eeeee M8, eeeee eeeeeeee eeeeeeeee eeeeeeeeee. Meeee eeeeeee, Me8M (888eM) eee eeeee eee eee eeee eee eeeeee eeee M8M (8×88eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeee eeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeeeee eeeee); eeeee: 8888%. Mee eeeeeeee eeee eeeeeeeeee ee eeeeeeeee eeeeeeeeeeeee eeee eeee eeeee ee eeeeeeeee eeeeeee.

Meee Meeeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M8MM8 (88.8eeee) eee (MeM)8MM (888eeee) eeee eeeeeee eeeeeeee eeee eee eeeeeeee eeeee. Mee eeeeee (8.8eeee) eee eeeee ee eee eeeeeee eeeeeee ee eeeeee eeeeeeeeeee (88°M). M eeee ee M8 eee eee eeee ee eeeeee eee MM8 eeeeee ee e eeeeeeeee. Meeeeee (8.8eM) eeee eeeeeeeee eeeeeeeeeeee eee eeeeeee eeee M8M (8.8eM) eee Me8M (8.8eM). Mee eeeeeee eeeee eee eeeeeeee ee MM eee MM/MM; eeeee: 88888%.

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

8-Meeeeeee (88.8ee, 8.88eeee), Me8MM8 (88.8ee, 8.88eeee), eee (MeM)8MM (8eM, 88.8eeee) eeee eeeeee ee e eeee eeee eeeeeeee eeee e eeeeee eee eee eee eeee eee eeeeee ee 888°M eee 8e. Meeee eee eeeeeee eee eeee eeeeee ee ee, eee eeeeeeee eeeeeeeee eeee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88); eeeee: 88ee (eeeee).

Meee Meeeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eee eeeeee (88eeee), MMM (88eeee), (MeM)8MM (888eeee), eee MeMM ee MMM (88eM) eee eeeeee eeeeeee e eeeeeeeeee-eeee eeeeeeeee eeeeeee eeeeeeeee ee 888°M ee 8MMe. Mee eeeeeeee eeeeeeee eeee eeeeeeee ee MMMM eeeee eeee eeee (8eee). Me eee eeee ee 8,8,8-eeeeeeeeeeeeeee, MMMM (88eeee) eee eeeeeee ee eee eeeeeee eeeeee eeeeeee eeeeeee eee eeeeeee; eeeee: 8888%.

Mee eeeeeee eeee eeeeeeee ee eee eeeeeee eeeeeeee eeeeeee eee ee 88°M, ee eeeee e eeeeeeee eeeee eee eeeeeee eeee eee eeeeee (8.8eeee), MMM (8.8eeee), eee (MeM)8MM (888eeee). Mee eeeeeee eee eeeeee ee 88°M eee 8888e eee eee eeeeeeee eeee eeeeeeee ee MMMM; eeeee: 8888%.

Meee Meeeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeee eeeeeee ee eeeeeeeee eee eeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeeee eee ee e eeeeeeee eeeee eeeeeeeeee.

Me e eeeeeee eeee ee eee eeeeee (8.88eee) ee 8,8-eeeeeee (88eM) ee 88°M (eee eeee eeeeeeeeeee) eee eeeee eeeeeee eeeeeeeeee MMM (88e) eeeeeeeeee eeeeeeeeeeeee 88 ee% M8M. Meee, Me8MM8 (8.88eee) eee eeeee ee e eeee ee 8 eeeee ee 8eee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeee ee MMM. Meeee eeeeeeeeee ee eee eeeeeeee (8.8e), eee eeeeeee eee eeeeeeee ee eeeeee eee eeeee eeeeeeee eee eee eeeeeeee eee eeeeeeeee; eeeee: 8888%.

Meee Meeeee Meeeee (e.e., 88); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeee (8eeee) eee eeeeeee eeee MeMMM8M (8eeee) ee eee MMM (8eM) ee ee (88°M eee eeeeeeeeeeee) eee 88eee. Me8MM8 (8.8eeee; 8eeee ee eee eeee ee eeeeeeeee eeeeeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee eee 8.88e. Mee eeeeeee eee eeeeeee ee eeeeeeeeeeee, eee eee eeeeeee eeeeeee eeee 8% ee MeMM (88eM), eee eeeeeeeee (Me8M). Meeeeee ee eee Me8M eeeeeeee eee eeeeeee, eeeee eeeeee ee eeeeeee eeeeeeeeeeee ee eeee eeeee. Meeeeeeee eeeeee eee eeeeeeeee eee eeeeeeee, eeeeeeee eeeeeeeeee, eeeee eeeeee eee eeeee ee eeeeeeeee eeeeeeeeeeee.

8-Meeeeeeeeeeeee Meee (88):[‌88‌]

MMMMMMM: Meeeeeee eeeeeee ee eeeeeeeee eee eeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeeee eee ee e eeeeeeee eeeee eeeeeeeeee.

Me eeeeeeeeeeeeeee (8.8eM) ee e eeee eeee eee eeeeee eeeee e eeee ee 8,8-eeeeeeeeeeeee (8.8eM) eee Me8MM8 (888ee, 8eeee). Meeee 8eee, eeee eee eee eeeeee eeee eeeeeeeeeee, eeeeeeeee eeee (888ee, 8eeee) eee Me8M (888ee, 8eeee) eeee eeeeeeeee ee eeeeeee (8.8eM) eee eee eeee eee eeeeeeeee eeeee ee eeee eee eeeeeeeee eeeee. Mee eeee eee eeeeeee eeee Me eeee eee eee eeeee eeeee eee eeeeeee eeeeeeeeeeee ee ee eee 8e. Mee eeeee eeeee, eeeeeeeeee ee eee eeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeee/eeeeeee, eee eeeeeeeee eeee eee eeeeeeee eeeee eee eee eeeeeee eee eeeeeeeeee ee e eeeeee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee 8:8); eeeee: 888ee (88%).