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3.1.11.1.4 Method 4: Zinc-Catalyzed Reduction Reactions

DOI: 10.1055/sos-SD-103-00147

Wu, X.-F.Science of Synthesis Knowledge Updates, (20141328.

The Noyori group developed the first zinc-catalyzed reduction of carbonyl compounds.[‌232‌] In the presence of 1 mol% of zinc(II) methanesulfonate, excess lithium hydride [(LiH)n], and chlorotrimethylsilane, various aldehydes and ketones are transformed into the corresponding silyl ethers in excellent yields in dichloromethane or toluene at 28–40 °C for 25–50 hours. Interestingly, a catalytic amount of zinc powder is also effective to catalyze the reaction. According to X-ray induced Auger electron spectroscopy analysis, a zinc(II) species is the real catalyst for this lithium hydride surface reaction. Bell and Kassyk reported the preparation of a N,N,N′,N′-tetramethylethylenediamine complex of hydridozinc chloride and also the synthetic application of this complex.[‌233‌] The complex is prepared by the addition of zinc(II) chloride and N,N,N′,N′-tetramethylethylenediamine to zinc(II) hydride in tetrahydrofuran, and ketones and phenylacetylene are reduced with an equimolar amount of this complex in good yields. In addition, zinc(II) borohydride is an effective reducing reagent for the reduction of esters, ketones, aldehydes, carboxylic acids, nitro compounds, alkenes, and epoxides as well (for a review see ref[‌234‌]). These early studies illustrate that zinc hydride is an important reaction intermediate for zinc-catalyzed reductions. With respect to the reducing reagents, lithium hydride is much more stable and convenient then sodium hydride and zinc(II) hydride. However, the main problem for these methods is the generation of a large amount of metal waste, which is not compatible with sustainable development nowadays. With this background, efforts have been made to put to use silanes and hydrogen as hydride sources with only a catalytic amount of zinc catalyst.

Meeeee eeeeeeee eee eeee eeeeeee eeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeee (MMMM) ee eeeeeeeee (Meeeee 88).[‌888‌] Meeeeeeeeeeeeeeeeeeeeee ee ee eeeeeeeeeee eee eeeeee eeeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeee (eeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeeee ee MeMMeMe8). Meee 8 eee% ee eeee(MM) 8-eeeeeeeeeeeeee eee 8 eee% ee eeeeee eeeeeeeeeee, eeeeeee, eeeeeeeee, eeeeeeee, eee eeeeee eee eeeeeee eeee 8–8 eeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeee eeeee ee 88 °M (Meeeee 88). Me eeeeeeee eeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeee. Me eee eeee ee eeeeeeeee ee eeeeee eeeeeeee, eeee(MM) eeeeeeee ee eeee ee eeeeeeeee eeeeeeee, eee eeeeeeeeeeee ee eeeeeee ee eeeeeeee eeee eeee(MM) eeeeeee ee eeee ee eeeeeeee eeeee eeee eeeeeeeeee. Meeeeeeeee eee ee-eeeeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeee eee eeeeee eeeee ee ee eeee eeeeee eeee eeeeeee eeee M,M′-eeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee eee eeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee eeeeeee. Meee eeee eeeeeeeee eeeeee, eeeeeeee eee eeeeee eee eeeeeeee ee eeee eeeeee eeee eeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee ee eeee eeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌] Meeee ee eeeeeee eeeeeeeeeee eeeeeee, eeeee­eee(eeeeeee)eeee(MM) eeeeeeeee eeee eeeee ee ee eee eeee eeeeee eeeeeeee eeeeeeeeeeeee.

Meee eeeeeeee, eee eeeeee ee Meeeeeee eee Meeeee eeeeeeeee eeeeeee eeeee eeeeeee eee eee eeee-eeeeeeeee eeeeeeeeeeeeeee ee eeeeeee.[‌888‌‌888‌] Mee eeeeeee, eeeeeee eee eeeeeee ee eeee eeeeee eeee eeee-eeeeeee eeee eeeeeeeee (e.e., 88) eeee eeeeeeeeee M,M,M-eeeeeee (Meeeee 88). Meeee ee, eeee eeeee eeee eeeeeee eeeeeeeee eeeeeee eee eeeeeeeeeeee (Meeeee 88) eee eeee ee eeee ee eeeeeeeee eeeeeee eee eee eeee-eeeeeeeee eeeeeeeeeeeeeee ee eeeeeee.

Meeeee 88 Meee-Meeeeeeee Meeeeeeee ee Meeeeee[‌888‌‌888‌]

Meee(MM) eeeeee eee eeee eeeee ee ee ee eeeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeeeee eeee eeeeeee.[‌888‌] Meeeeeee eee eeeeeeee eeeee eeeeeee-eeee eeeeeeeeee eee eeeeeee eeeee-eee eeeeeeeeee.

Meeee ee eeeee eeeeeeee eeee,[‌888‌] Meeeee eee ee-eeeeeee eeeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee eeeeeee.[‌888‌] Me eee eeeeeeee ee eeeeeeeeeee ee eeee(MM) eeeeeeeeeeee eeee e eeeeee ee­eeeee ee eeeeeee ee eee eeeeee (e.e., 88 eee 88), eeeeeee eee eeeeeee ee eeee eeeeeeee 888 ee eeee eeeeee eeee ee ee 88% eeeeeeeeeeee eeeeee (Meeeee 88). Mee eeeeeeee eee eeee ee eeeeeee eee ee 8-ee eeeee eee eee eeeeee ee eeeeee eeeeeeeee eeee eee eeeeeeee eeeeeee ee eeeeeeeeeeee. Meeee ee eee eeeee ee Meeeee, eeeeeee eeeee eeeeee eeeeeeee eeee eeee eeeeeeeee eee eee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeeee.[‌888‌‌888‌] Meeeeeeeee eee ee-eeeeeee eeeeeeeee e eeeeeeeeeeeee eeeee ee Meeeee‘e eeeeeeeee eeeeee.[‌888‌,‌888‌] Meeee eeeee eeeeeeee ee­eeeee eeeeee 88 (Meeeee 88) eeeeeeee 88% eeeeeeeeeeee eeeeee, eeee 88% eeeee, eee eee eeeeeeeee ee (M)-8-eeeeeeeeeeeee (eee-888; Me8 = Me; M8 = M). Me eeeeeeeeee, eee eeeeeeee ee­eeeee eeeeeee eeeee >88% eeeee eeee 88–88% eeeeeeeeeeee eeeeee. Meee eeeee eeeee eeeeeeee eeeeee eeeeeee eeeeeee 88888 eeee eeee eeee eeeeeeeeeeee ee eee eeeeeeeeeeeeeee ee eeeeeee eee ee eee eeeee eeee eeee eeeeee eee eeeeeeeeeeee eeeeeeee eee eeeeeeee eeee eeeeeeeee eeee eeeee eee eeeeeee (Meeeee 88). Mee eeeeeee, eeeee eeeeeeee eee eee eeeeeeeeeee ee M-eeeeeeeeee 8-eeeeeeeeeeee eeee eeeeeeee eeeee eeee(MM) eeeeeee (8 eee%), eeeeee 88 (8 eee%), eee eeeeeeee(eeeeee)eeeeee eeee 88–88% eeeee eee 88–88% eeeeeeeeeeee eeeeee.[‌888‌] Mee eee eeee eeeeeee eeee eeeeeeeeeee eeeeeeeeee 888, 88 eeeeeeee ee M-eeeeeeeeee 8-eeeeeeeeeeee 888 eeee eeeeeeee eeee 88–88% eeeee eee 8–88% eeeeeeeeeeee eeeeee. Mee eeeeeeeee ee eee eeeeeeeeee eeeeeeeee ee eee eeeeeeee eee eeeeeeeeeeee eeee e eeeeeee eeeeeeeeee eeeeee (MMM) eeeee ee eee eeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee eeee eee eeee eeeeeee, eee eee eeeeeeeeeee ee eee eeeeee eeeeee eeeeeeee ee eee eeeeeee eee eee eeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee Meee-Meeeeeeee Meeeeeeee ee Meeeeee[‌888‌,‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeeeeee 88

Me8 M8 eee% ee Me8Me Meeeee (eee%) Meeeee Meeeee (%) ee (%) Mee
Me M 8 88 (8) MMMM e.e. 88 (M) [‌888‌]
8-MeMM8M8 M 8 88 (8) MMMM e.e. 88 (M) [‌888‌]
Me Me 8 88 (8) MMMM e.e. 88 (M) [‌888‌]
8-eeeeeeee M 8 88 (8) MMMM e.e. 88 (M) [‌888‌]
Me M 88 MMMM 88e 88 (M) [‌888‌]
Me M 8 88 (8) MMe(MMe)8 888 88 (M) [‌888‌]
Me M 8 88 (8) MMMM 88 88 (M) [‌888‌]
Me M 8.8 888 (8.8) Me8MeM8 88 88 (M) [‌888‌]
8-Mee M 8.8 888 (8.8) Me8MeM8 88 88 (M) [‌888‌]

e e.e. = eee eeeeeeee.

e Meeee (MMMM/eeeeeeeeeeee/Me8Me/88) 88:88:8:8; [eeeeeeeeeeee] = 8.88 M.

Meeeeeeeeeee ee eeeeeee ee eee eeeeeeeeeee ee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee eeee M,M′-eee(8-eeeeeeeeeeeee)eeeeeeeeeee-8,8-eeeeeee (M,M-eeeee) ee eee eeeeeeee ee eeeeeeeeeeeeee ee 8 °M. Mee eeeeeee ee eeeeee ee 88% eeeee eeee 88% eeeeeeeeeeee eeeeee. Mee eeeeeeeee eeeeeee eeee(MM) eeeeeeee eeeeeee [MeMe8(M,M-eeeee)] ee eeeeeeee ee eee eeeeeeee ee eeee(MM) eeeeeeee eeee eee eeeeee, eee eeee eeeeeee eee eeeeeeeeeeeee ee eeee.[‌888‌]

Me 8888, Meeeeee, Meeee-Meeeee, eee ee-eeeeeee eeeeeeee e eee eeeeee eeeeeee eee(eeeeeeeeeeee) eeeeee 888 eee eeee-eeeeeeeee eeeeeeeeee eeeeeeeeee.[‌888‌] Meeeeee eee M-(eeeeeeeeeeeeeeeee)eeeeee eee eeeeeee ee eeee eeeeee eeee eeee eeeeeeeeeeee eeeeee (Meeeee 88). Mee eeeeeee eeee eee eeeeee eeeeeeee, eee eee eeeeeee ee eeee eeeeee eeee eeeeeeeee eee eeee eeee eeeeeeeeeee eee eeeeeeee.

Meeeee 88 M Meeeeee Mee(eeeeeeeeeeee) Meeeee eee Meee-Meeeeeeee Meeeeeeeee[‌888‌]

Me eeeeeeee ee eee eeeeeee eeeeeee, eeeeeee eeeeeeeeeeeeee-eeeee eeeeeee 888888 eeee eeee eeeeeeeeeee eee eeeeeeeeeeee ee eeee (Meeeee 88).[‌888‌‌888‌] Me eee eeeeeeeeeee ee eeeee eeeeeee eeee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeee, eeee eeeeee ee eeeeeeee 888888 eee eeeeeeee eeee eeee eeeeeeeeeeee eeeeee.

Meeeee 88 Meeeeeeeeeeee-Meeee Meeeeee eee Meee-Meeeeeeee Meeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

Me8 Meeeee Meeee (%) ee (%) Mee
Me 888 88 88 [‌888‌]
8-MM8M8 888 (M8 = e-Me) 88 88 [‌888‌]
8-MeM8M8 888 (M8 = eMe) 88 88 [‌888‌]
8-MeM8M8 888 (M8 = e-Me) 88 88 [‌888‌]
8-M8MM8M8 888 (M8 = e-Me) 88 88 [‌888‌]
8-eeeeeeee 888 (M8 = eMe) 88 88 [‌888‌]

Meeeeeee, eeeeeee eeeeee Meeeee eeee eeeeeee (e.e., 888) eee eee eeeeeeeeeeeee eeeeeeeee eeee eeee eeee eeeeeeee ee Meee, Mee, eee ee-eeeeeee.[‌888‌] Meee eeeeeeee eeeeee eeeee eee eeeeeeeeeeeee eeeeeeee 888 ee eeee eeeeee eeee eeeeeeeee eeeeeeeeeeeeeeeeee (Meeeee 88). Me eeeee eeeeeeee eeeeeeeee, eee eeeeeee eeeeeeeee eee eeeeeeeeee ee eeee eeeeee eee eee eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeeeeeeee. Mee eeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeee ee eee eeeeeeeeeee eeeeeeeeeeeeeee eeee e eeeee eeeeee ee eee eeeeeeeeeeee eeeeee. Mee eeeeeeeee eeeeeeeeeee eeeee eeeeeee eeee e eeeeee α-eeeee eeee ee eeeeeee eee eee eeeeeeeee eeeeeeeeee. Me eeeeeeeeeeeee eeeeeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeee eee eeeeeee ee Meee eee ee-eeeeeee.[‌888‌] Me eeeee eeeeee eeeeeeeeeeeeeeeeeeeee ee eeeeeeeee, 88% ee eeeeeeeeeeee eeeeee ee eeeeeeee eeeee 8.8 eeeeeeeeeee ee eeee(MM) eeeeeeeeeeeeeeeeeee­eeeeee ee eee eeeeeeee.

Meeeee 88 Meeeee Meee Meeeee eee Meee-Meeeeeeee Meeeeeeee Meeeeeee[‌888‌]

Meeeeeeeeee 88

Me8 Meeee (%) ee (%) Mee
8-MeM8M8 88 88 [‌888‌]
8-MeM8M8 88 88 [‌888‌]
8-M8MM8M8 88 88 [‌888‌]
8-M8MM8M8 88 88 [‌888‌]

Mee eeeeeeeee ee eeeeee eeeeeeee ee eeeeeeeeeee eeeeeeeee eee eee eeeeeeeeee ee eeeeee eeeeee.[‌888‌‌888‌] Me eeeeeeeee, eee eeeeeeee eeeeeee eeee eee eeeeeee eee eee eeeeeeeee ee eeeeeee eee eeee ee eeee eee eee eeeeeeeee ee eeeeee eeeee eeeeeee eeeeeeeeee. Meeeeee eee ee-eeeeeee eeeeeeeee e eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeeee ee M-eeeeee(8-eeeeeeeeeee)eeeee eeeee 8,8′-ee-8-eeeeeeeee ee eeeeee.[‌888‌] Meeeeeee ee eeee ee eee eeeeeee eee eeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeeee. Mee eee ee-eeeeeee eeeeeeee e eeee/eeeeeee eeeeee eee eee eeeeee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeee.[‌888‌,‌888‌] Meee eeeeeeeee eeeeee eee eeeeeee eeeeee ee eeee eeeeee eeee eeeeeeeee eeeeeeeeeeee eeeeee (Meeeee 88). Mee eeee–eeeeeeeeeeee 888 eeeeee (eee Meeeee 88) ee eeee eeeeeeeee eee eee eeeeeeeee ee eeeeee.[‌888‌]

Meeeee 88 Meee-Meeeeeeee Meeeeeeeee Meeeeeeee ee Meeeee[‌888‌,‌888‌]

Meee eeeeeeee, Meeeeeee eeeeeeeee e eee-eee eeeeeeeee ee eeeeeeeee eeeeee ee eeee-eeeeeeeee eeeeeeeee eeeeeeeee.[‌888‌] Meeeee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeee ee eee eeeeeeeeeeeeeee eeeeeeee eee eee eeeeeeeee ee eee ee eeee eeeeee eeeee ee eeeeeeeeeeee ee ee eeeeeeee eeee ee eeeee. Meeeeeeeeeeeeeeeeeeeeee ee eeee ee ee eeeeeeeeeee eeeeeee eeeeee. Meeeeeeee eeeeee ee eee eeeeeeee 888 eee eeeeee eeee e eeeee eeeeeeeeee eeeee eeeeeeeee (Meeeee 88).[‌888‌] Meeeeeeeee, Meeeee eee ee-eeeeeee eeeeeeee ee eeeeeeeee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee ee eeeeee eeeee eee eeeeee ee eeee ee eeeeeeeeeeeeee ee eeeeeee eeee eeeeee eeeee eee eeee eeeeeeeee eeeeee (Meeeee 88).[‌888‌] M eeeeeee ee eeeeeeeeee eeeeee eee eeeeeeeee eee eee eeeeeee eeeeeeee 888 eee eeeeee ee eeee eeeeee.

Meeeee 88 Meee-Meeeeeeee Meeeeeeee ee Meeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
8-e-MeM8M8 Me 88 [‌888‌]
8-MM8M8 Me 88 [‌888‌]
Mee Me 88 [‌888‌]
8-M8MM8M8 Me 88 [‌888‌]
8-eeeee Me 88 [‌888‌]
Me Me 88 [‌888‌]
Me Me 88 [‌888‌]

M8 M8 Meeee (%) Mee
Me 8-MeMM8M8 88 [‌888‌]
Me Me 88 [‌888‌]
8-MeM8M8 8-MeMM8M8 88 [‌888‌]
8-MeM8M8 8-MeMM8M8 88 [‌888‌]
eMe 8-MeMM8M8 88 [‌888‌]

Meee-eeeeeeee eeeeeeeee eeeeeeee ee 8-eeee-8,8-eeeeeeeeeeeeeeee eeeee ee eeee 8,8-eeeeeeeee eee eeee eeee eeeeeeee.[‌888‌] Meeeeeeeeeee, eeeeeeeeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeeeeeee eeeeeeeeee eeeee 8,8-eeeeeeee[‌888‌] eeeee eee ee eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeee eeeeee eeee eeeeee ee eeee.[‌888‌]

Meee eeeeeeeeeeee eeee ee eeee-eeeeeeeee eeeeeeeee ee eeeeee eee eeeeee eee eeeeeeeee ee Meeeee.[‌888‌‌888‌] Me eee eeeeeeee ee eeee(MM) eeeeeee eee eeeeeeee­(eeeeee)eeeeee ee eeeeeeeeeeeeeee, eeeeee eee eeeeee eee eeeeeee eeeee eeee eeeeeeeeee eee eeee eee eeeeeeeeeeeee eeeeeeee 888 eee eeeeee 888, eeeeeeeeeeee, ee eeee eeeeee (Meeeee 88). M eeeeeee ee eeeeeeeeee eeee eeeeeeeee eeeeeeeeee eeeeee eeee eeee eeeeeeeeeeee eeeeee, eeeeeeeee eee eeee eeeeeeee eeeeeeeeee eee eeee eeeeeeeee eeeeeeeee.

Meeeee 88 Meee-Meeeeeeee Meeeeeeee ee Meeeee eee Meeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
Me Me 88 [‌888‌]
Me Me 88 [‌888‌]
Me eMe 88 [‌888‌]
Me Me 88 [‌888‌]
8-M8MM8M8 Me 88 [‌888‌]
Me 88 [‌888‌]
eeeeeeeeee Me 88 [‌888‌]

M8 M8 M8 Meeee (%) Mee
Me Me Me 88 [‌888‌]
Me (MM8)8 88 [‌888‌]
8-MM8M8 (MM8)8 88 [‌888‌]
8-eeeeeeee (MM8)8 88 [‌888‌]
8-eeeee (MM8)8 88 [‌888‌]
8-eeeeeee (MM8)8 88 [‌888‌]
Me Me Me 88 [‌888‌]

Meeeeee eee eeeee-eeeeeeeee eeeeeeeee eeeeeeeee, eee eeeee eeee-eeeeeeeee eeeeeeeee ee eeeeeeeeee ee eeeeeeee eee eeee eeee eeeeeeeee ee Meeeeeee.[‌888‌] Meee eee eeeeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeeeeee eee e eeeeee ee eeeeeeeee, eeeeeeeee eeeeeeeeeeeeeeeeee eee eeeeeeee, eee eeeeeeee 888 eee eeeeeeee ee eeeeeeee ee eeeeeeeee eeeeee (Meeeee 88).

Meeeee 88 Meee-Meeeeeeee Meeeeeeee ee Meeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
Me Me 88 [‌888‌]
8-Mee 8-Mee 88 [‌888‌]
8-MeM8M8 8-MeM8M8 88 [‌888‌]
Me Me 88 [‌888‌]
8-M8MM8M8 Me 88 [‌888‌]
Me MMMM8 88 [‌888‌]
88 [‌888‌]
Me Me 88 [‌888‌]
(MM8)8 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

(M)-8-Meeeeeeeeeeee (888, Me8 = Me; M8 = M); Meeeeee Meeeeeeee eee Meee-Meeeeeeee Meeeeeeee ee Meeeeee Meeee Meeeeee 88 ee Meeeee:[‌888‌]

Me e eeeee-eeeeee 8-M eeeee, e 8 M eeee ee Me8Me ee eeeeeee (88.8 eM, 88 eeee) eee eeeeee 88 (8.88 e, 88 eeee) eeee eeeeeeeee ee eeeeeee (888 eM). Meeeeeeeeeee (888 e, 8.88 eee) eee eeeee ee eee eeeeeee eeeeeeee ee MMMM (888 e, 8 eee) ee 88 eee, eeeeeee eee eeeeeeeeeee eeeeeee 88 eee 88 °M. Meeee 88 e ee ee, eee eeeeeeeeeeee eee eeee eeeeeeee (MM eeeeeee ee ee eeeeeee eeeeee eeeeeeeeee ee 88% ee MMM). Mee eeeeeee eee eeeeee eeeeeeeeee eeee 88% ee MMM (888 e) (MMMMMMM: eeeeeeeee ee M8) eeee ee. 88 eee. Mee eeeeeee eeeee eeeeeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeee eee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee (88% eeeeee) eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 888 e (88%); 88% ee. Mee eeee eeeeee eee eeeeeeee eeeee 8.88 eeee ee eeeeee 88 eeeeeee ee 88 eeee.

(8M)-8-Meeeeeeee-8-eee 888; Meeeeee Meeeeeeee eee Meee-Meeeeeeee Meeeeeeee ee Meeeeee Meeee Meeeeeeeeee Meeeeeeeee 888 ee Meeeee:[‌888‌]

Me e 8-eM eeeee-eeeeeeee eeeee, e 8 M eeee ee Me8Me ee eeeeee (88.8 eM, 8.8888 eeee) eee eee eeeeeeeeeee eeeeee eeeeee (8.8888 eeee) eeee eeeeeeeee ee eeeeeee eeeeeeeee eeeeeee (8.8 eM) eee eeeeeee eeeee eeeee eee 88 eee. Meee, eee eeeeeeeeeee eeeeee (8.888 eeee) ee eee eeee ee eeeeeee (8 eM) eee eee eeeeee (8.888 eeee) eeee eeeee ee eee eeeeeee. Mee eeeeeeeee eeee eee eeeeeee ee ee eee 88 e. M 8 M eeee ee MeMM ee MeMM (8 eM) eee eeeee eeee eeeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eee ee eeeeeeeeee 8 e ee ee eee eeee eee eeeeeeee eeee eeeeeeeeee. Mee eeeeeeeeeee eee eeeeeeeee ee e eeeeeee ee M8M (88 eM) eee 88% ee MMe (8 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eee. ee MeMMM8, M8M, eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8).

(M)-8-Meeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me ee eeee-eeeee eeeee, eeeeee 888 (M8 = eMe ee e-Me) ee 888 (8.888 eeee) eee Me(MMe)8 (8.888 eeee) eeee eeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee 8–88 eee. Meeee MM8Me8 (8 eM) eee eeeeeeeeeeee eeeee eee eee eeeeeeeee eeee eee eeeeeee ee ee eee 8 e. Mee eeeeeee eeeeeeeee eeeeee (8.8 eeee) eee eeeee eee eee eeeee eeee eeeeee eeee eee eeeeee ee −88 °M. Meee eeeeeeeeeeeeee (8.8 eeee) eee eeeee eeeeeeee. Mee eeeeeee eee eeee eeeeeee eeeeeeee ee e eeeeeee ee −88 °M eee 88 e. Mee eeeeeee eee eeeeeee eeee Me8M (8 eM), eee eeee 8 M MeMM (8 eM) eee eeeeeeeee eeeee (MMMMMMM: eee eeeeeeeee). Mee eee eeeeee eeee eeeeeee eee 88–88 eee eee eeeeee eeee eeee eeeeee eee eeeeeee eeeee eeeeee eeee eeeee. Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 8 eM). Mee eeeeeee eeeeee eeee eeeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeeeeeee/Me8M 8:8 ee 8:8).

(M)-8-Meeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me e Meeeeee eeeee, e 8 M eeee ee Me8Me ee eeeeeee (8.88 eM, 8.88 eeee) eee eeeeee eeeeee 888 (8.88 eeee) eeee eeeeeeeee ee MMM (8 eM) eee eeeeeee eeeee M8 eee 88 eee. Meee, e-MeMM (8.8 eM) eee eee eeeeeeeeeee eeeeee (8 eeee) eeee eeeee. MMe(MMe)8 (8.88 eM, 8.8 eeee) eee eeeee eeeeee ee eee eeeeeee, eeeee eee eeee ee −88 °M eee 88 e. Mee eeeeeee eee eeeeee eeee 88% ee MMM (8 eM) eee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeee eeeee eee eeeeee eeee M8M (8 × 8 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8).

8-Meeeeee-M-(8-eeeeeeeeeee)eeeeeee (888, M8 = Me; M8 = 8-MeMM8M8); Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeee, e eeeee eeee eee eeeeeee eeee Me(MMe)8 (88.8 ee, 8.88 eeee), eeeeeeeeeeeeeee (88.8 ee, 8.88 eeee), eee 8-eeeeeeeeeeeeee (88.8 ee, 8.8 eeee). Meeeeee (8.8 eM) eee e eeeeeeee eeeeeee eee eeee eeeee. Meeeeeeeee, eee eeee eee eeeeee eeee e eeeeee eeeeeeee eeee e eeeeeee eee eee eee ee ee eeeee eeeee, eeeee eee eeee eeeeee eeee eee eeeeeeeee. Meee eeeeee, eee eeeeeeeee eee eeeeee eeeee eeeee eeee M8, eeee eeeeeeeeeee ee 88 eee, eee eeeeee ee 888 °M eee 88 e. Mee eeeeeeeee eee eeee eeeeee ee 88 °M eee eeeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee eee eeee eeeeeee; eeeee: 88%.

Meeeeee Meeeeeee 888; Meeeeee Meeeeeeee eee Meee-Meeeeeeee Meeeeeeee ee Meeeee:[‌888‌]

Me eeee-eeeee 88-eM Meeeeee eeee eeeeeeeeee e eeeeeee eee eee eeeeeee eeee Me(MMe)8 (8.8 eeee). Meeee MMM (8 eM) ee eeeeeee (8 eM) eee MMeMe(MMe)8 (8 eeee) eeee eeeee, eeeeeeeeeeee, eeeee eeeeeee eee Meeeeee eeee eeee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee 88 °M eee 88 eee. Mee eeeee (8 eeee) ee eeeee MMM (8 eM) ee eeeeeee (8 eM) eee eeeee­eeeeee ee eee eeee eeeee eeeee. Mee eeeeeee eee eeeeeee ee 88 °M ee 888 °M eee 88 e eee eeeeeeeee ee MMM. Meeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee, eee eeeeeee eee eeeeeeeeee eeeeeee eeee eee eeeeeeee eeeeeeee eeeeeeeeee (888 µM) eee e 88% eeee ee MMM ee MeMM (8 eM) ee e 88-eM eeeeeee eeeee eeeeeeeee eee eeee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeeee eee eeeeeeeee ee MeMMe eee e eeeeee eee eeeee, eeeee eee eeeeeeeee ee MM eeeeeeee.

Meeeee 888; Meeeeee Meeeeeeee eee Meee-Meeeeeeee Meeeeeeee ee Meeeee:[‌888‌]

Me eeee-eeeee 88-eM Meeeeee eeee eeeeeeeeee e eeeeeee eee eee eeeeeee eeee Me(MMe)8 (8.8 eeee). Meeee MMM (8 eM) eee MMe(MMe)8 (8 eeee) eeee eeeee, eeeeeeeeeeee, eeeee eeeeeee eee Meeeeee eeee eeee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 eee. Meee, eee eeeee (8 eeee) ee eeeee MMM (8 eM) eee eeeeeeeeeee ee eee eeee eeeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 88–88 e eee eeeeeeeee ee MMM. Meeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee, eee eeeeeee eee eeeeeeeeee eeeeeee eeee 8 M ee MeMM (8 eM) ee e 88-eM eeeeeee eeeee eee 8 e eee eeee eeeeeeeee eeee MeMMe (8 × 8 eM).Mee eeeeeeee eeeeeee eeeee eee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeee eee, MeMMe/eeeeee/Me8M (8%)] ee eeeeee eee eeee eeeeeee eeeeeee.

Meeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeeee eeee eee eeeeeee eeee Me(MMe)8 (8.888 eeee, 8.8 eee%) eee eee eeeeeeeee (8.88 eeee), eee MeMeM8 (8.8 eeee) eee eeeee. Meeee eeeeeeee ee eeeeeee (8.8 eM), eee eeeeeee eee eeeeeee ee e eeeeeeeee eee eeee ee 888 °M eee 88 e. Mee eeeeeee eee eeeeee ee ee eee eeee eee eeeeeeee (eeeeeeee eeeeeeee) eee eeeee. Mee eeee eee eeeeeee eeee MM8Me8 eee ee eeeeeee eee eeeee eee MM eeeeeeee (88-e Mee-8ee eeeeee, 88–888 °M). Mee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee.

References


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