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2.5.6 Cyanation through Direct C—H Bond Activation

DOI: 10.1055/sos-SD-208-00361

Yan, G.; Zhang, Y.; Wang, JianboScience of Synthesis: Cross Coupling and Heck-Type Reactions, (20132542.

Transition-metal-catalyzed direct and selective C—H functionalization for the construction of C—C bonds is an efficient and straightforward method in organic synthesis. In 2003, Murahashi and co-workers described the first ruthenium-catalyzed oxidative cyanation of C—H bonds adjacent to the nitrogen atom of tertiary amines with sodium cyanide as the cyanating agent (Scheme 20).[‌39‌] This procedure provides a convenient method for the synthesis of α-aminonitriles 21, which are also useful for the synthesis of α-amino acids and 1,2-diamines. It is important to note that the presence of acetic acid is essential and a 3:1 mixture of methanol/acetic acid is employed as solvent. Recently, an analogous ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide as oxidant has been reported; the participation of hydrogen cyanide, which is formed in situ from sodium cyanide and acetic acid in methanol, has been experimentally confirmed.[‌40‌]

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

Meeeeeeeeee 88

Me8 Meee (e) Meeee (%) Mee
Me 8 88 [‌88‌]
8-Mee 8 88 [‌88‌]
8-Mee 8.8 88 [‌88‌]
8-MeMM8M8 8 88 [‌88‌]
8-MeM8M8 8 88 [‌88‌]

Meeee ee eeee eeeeeeeeeee, eeeee eeeeeeeee eeeeeee, eeee ee eeeeeeee(M) eeeee, eeee(MM) eeeeeeee, eee e eeee eeeeeee, eee eee eeeeeeeee ee eeeeeeee eeeeee eeee eeee eeeeeeee eeeeeeeee ee Meee,[‌88‌] Meeee,[‌88‌] eee Mee,[‌88‌] eeeeeeeeeeee (Meeeee 88). Meeee eeeeeeeee eeeeeee eeee eeee eeeeeeeeee ee eeee eee eeeeeeeeeeeee α-eeeeeeeeeeeee 88, eeeee eee eeeeeeeee eeeeee eeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeeeeeeee.

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

Meeeeeeeeee 88

M8 M8 M8 M Meeeeeee Meeee (%) Mee
Me Me M Me M8M8 88 [‌88‌]
Me Me M MMM MeMe8 88 [‌88‌]
Me Me M MMM [MeMe8(eeee)]Me 88 [‌88‌]
8-Mee Me M Me M8M8 88 [‌88‌]
8-Mee Me M MMM MeMe8 88 [‌88‌]
8-Mee Me M MMM [MeMe8(eeee)]Me 88 [‌88‌]
Me (MM8)8 Me M8M8 88 [‌88‌]
Me (MM8)8 MMM MeMe8 88 [‌88‌]
Me (MM8)8 MMM [MeMe8(eeee)]Me 88 [‌88‌]
Me (MM8)8 Me M8M8 88 [‌88‌]
Me (MM8)8 MMM MeMe8 88 [‌88‌]
Me (MM8)8 MMM [MeMe8(eeee)]Me 88 [‌88‌]
Me Me M8M8 88 [‌88‌]
Me MMM MeMe8 88 [‌88‌]
Me MMM [MeMe8(eeee)]Me 88 [‌88‌]

Meeeeeee, eee eeeeeeeeee-eeeee-eeeeeeeee eeeeeeeee eeeeeeeee ee eeee ee8 M—M eeeee eee eeee e eee eeeee. Me 8888, Me eee ee-eeeeeee eeeeeeeee e eeeeeeeee-eeeeeeee eeeeee-eeeeeeee eeeeeeeee ee M—M eeeee eeeee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeee ee eeeeeee eeeeeee.[‌88‌] Meeeeeeeeeee, Meeee eee ee-eeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeee-eeeeeeeee eeeeee eeeeeeeee ee 8-eeeeeeeeeeee M—M eeeee eeee eeeeee(M) eeeeeee[‌88‌] eee eeeeeeeee eeeeeeeeeeeeeeee(MMM)[‌88‌] ee eeeeeeeee eeeeee (Meeeee 88). Me 8888, Meeeeʼe eeeee eeeeeeeee e eeeeeeee eeeeee ee eeeee eee “MM” eeee ee eeeeeeeee ee eeee eeee eee eeeeeee eeeeeeeee eeeeeeeeee, eeeeeee eee eeeeeeeeeeeeeeeee. Meee eeeeeeeee eeeeeeeee eee eeee eeeeeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeeee ee eeee M—M eeeee.[‌88‌] Meeee eeeeeeeeee eeeeeeeee eeeeee eeeeeee ee eeeeee eeeeeeee eeeeeeee 88.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee Meeeeeeee ee Meeee M—M Meeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 Meeeeee Meeeee eee% ee Me(MMe)8 Meeee ee MeMe8 Meeee(%) Mee
M M8[Me(MM)8] 8 8 88 [‌88‌]
M MeMM 88 8.8 88 [‌88‌]
M MM8/MMM 88 8.8 88 [‌88‌]
MMe M8[Me(MM)8] 8 8 88 [‌88‌]
MMe MeMM 88 8.8 88 [‌88‌]
MMe MM8/MMM 88 8.8 88 [‌88‌]
Me M8[Me(MM)8] 8 8 88 [‌88‌]
Me MeMM 88 8.8 88 [‌88‌]
Me MM8/MMM 88 8.8 88 [‌88‌]
Me M8[Me(MM)8] 8 8 88 [‌88‌]
Me MeMM 88 8.8 88 [‌88‌]
M M8[Me(MM)8] 8 8 88 [‌88‌]
M MeMM 88 8.8 88 [‌88‌]
M MM8/MMM 88 8.8 88 [‌88‌]
MM M8[Me(MM)8] 8 8 88 [‌88‌]
MM MeMM 88 8.8 88 [‌88‌]

Meeeeeeeee-eeeee-eeeeeeeee eeeeeeeee eee eeeeeeeeeeee M—M eeeeeeeeeeeeeeeee ee eeeeeee eee eeee eeeeeeeeeee eeeeeee ee eeeeee eeeee. Me 8888, Meee eee ee-eeeeeee eeeeeeee[‌88‌] eee eeeee eeeeeeeee-eeeeeeeee eeeeeeeee eeeeeeeee ee eee 8-eeeeeeee ee eeeeeee eeee eeee eee eeeeeeee eeeeeeeee eeeeeeeeeeeeeeee(MM) {M8[Me(MM)8]} ee eee eeeeeeeee eeeee. Meeeeeeeeeee, Meeee eee ee-eeeeeee eeeeeeeee e eeeeeeeee-eeeeeeeee eeeeeeeee ee eeeeeee eeee eeeeee(M) eeeeeee ee eee eeeee eeeeee.[‌88‌] Me 8888, Meeee eee ee-eeeeeee eeeeeeeee eeeee eeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeeee eeeeeeee ee eeeeee M—M eeeee eeeee e eeeeeeeeeee ee eeeeeeee eeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeee ee e eeeeeee eeeeee (Meeee 8, eeeeeee 8–8).[‌88‌] Meee eeeeeeeee eeeeeeeeee e eeeeeeeee eee eeee eeeeeeeee ee eeeeee M—M eeeee. Me 8888, Meeeeeee eee ee-eeeeeee eeeeeeee e eeeeee eee eee eeeeee-eeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeeeee eee eeeeeee eeeee ee eeeeee eeeeeee.[‌88‌] Mee eee ee eeeeee ee e eeee eeeeeee eeeeee eee eeeeeeeeeeeeee eeeeeeeeee eeeeeeeeee/eeeeeeeee ee eeeeeeeeeeee eeee eeeeee M—M eeeee, eeeeeeeeeeee, eee eeeeeee. Me 8888, Meee eee ee-eeeeeee eeeeeeeee eee eeeeeeeee-eeeeeeeee eeeeeeeee ee eeeeeee eee eeeeeeeeeee ee eeeee eeeeeeeeeeeeeeeee ee eeee ee eee eeeee eeeeee.[‌88‌] Meeeeee, eee eeeeee ee eeee eeeeeeee eee eeeeeeee eee eee eeeeeeee eeeeeeeeee eee eeeeee eeeeeeeeeee.

Meeee 8 Meeeeeeeee-Meeee-Meeeeeeee Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeee[‌88‌,‌88‌]

Meeee Meeeeeeee Meeeeeee Meeeeee Meeeee Meeeeee Meeee (%) Mee
8 MeMe8, Me(MMe)8 MM8MMM8, MMMM 88 [‌88‌]
8 MeMe8, Me(MMe)8 MM8MMM8, MMMM 88 [‌88‌]
8 MeMe8, Me(MMe)8 MM8MMM8, MMMM 88 [‌88‌]
8 MeMe8, Me(MMe)8 MM8MMM8, MMMM 88 [‌88‌]
8 MeMe8, Me(MMe)8 MM8MMM8, MMMM 88 [‌88‌]
8 MeMM, 8,88-eeeeeeeeeeeeee MeMM 88 [‌88‌]
8 MeMM, 8,88-eeeeeeeeeeeeee MeMM 88 [‌88‌]
8 MeMM, 8,88-eeeeeeeeeeeeee MeMM 88 [‌88‌]
8 MeMM, 8,88-eeeeeeeeeeeeee MeMM 88 [‌88‌]

Meeeeeee eeeeeeeeeee eeeeeeee eeee eeee eeeeeeee ee eee eeeeeeeeee-eeeee-eeeeeeeee eeeeeeeee ee M—M eeee ee eeeeeeee eeeeeeeeeeee, eeeeeeee eeeeee eeeeee eeeeeeeee eee eeeeeeee ee eeeee eeeeeeeeee ee eee eeeee eeeeeee, eeeee eee eeeeeeee eeeee eeeeeeeee eeeeeeeeeee. Meeee, eeeeeeeeeee eeeeeeeee eeeee-eeee eeeeeeeee eee eee eeeeeeeeeeee ee M—MM eeeee eeee eeeeeeeee eeeeeeeee. Meeeeeee, Meee eee ee-eeeeeee eeeeeeee e eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee eeeeeeeee eeeeeeee eee eee eeeeee eeeeeeeee ee eeeeeee eee eeeeeeee eeee e eeee eeeee eeeeeeeeeeeee eeeeeeeee eeeee (Meeeee 88).[‌88‌] Mee eeeeeeee eeeeeeee ee eeee eeeeee eee eeee eeeeeeeee eeeeeeeeeeeeeeee eee eee eeeeeee eeeeeeee 88. Meeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee-eeeeeeeee eeeeeeeee eeeeeeeee, eeee eeeeeeee eeeeeeee eeeeeeeee eeeeeeeeee eeeee eeeeeeeee eee eeeeeee eeeeee eeee eeee eeeeee eee eeeeeee eeeeeeeeee. Meee eeeeeeeeeee eeee eee eeee eeeeeeeeee-eeeee eeeeeeeee ee eee eeeeeee.

Meeeee 88 Meeee Meeeeeeeeee–Meeeeee Meeee Meeeeee Meeeeeeee Meeeeeeee ee Meeeeee eee Meeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 eee% ee MM8•MMe8 Meeee (%) Mee
88 88 [‌88‌]
88 88 [‌88‌]
88 88 [‌88‌]
88 88 [‌88‌]
888 88 [‌88‌]
88 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-[Meee(eeeeee)eeeee]eeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM:Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M 88-eM, eeee-eeeee, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee e eeeeeee eeeeee eeee M8 (8 eee) eee eeeeeee eeee MeMe8•eM8M (88 ee, 8.88 eeee) eee MeMM (88 ee, 8.8 eeee). MeMM (8.8 eM) eee eee eeeeeeeeeeeee (8.8 eeee) eeee eeeee ee eee eeeee, eee eeee MeMM (8.8 eM) eee eeeee ee eeeeeee. Mee eeeeeee eee eeeeeee eeeee M8 ee 88 °M. Meeee 8 e, eee eeeeeee eee eeeeee eeee ee MeMMM8, eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeee eeee eeeee eee eeeee (Me8MM8).

α-Meeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeee(M) Meeee:[‌88‌]

MMMMMMM:Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M 88-eM, eeeeee eeeeee, eeeee-eeeeeeee eeeee eeeeeeee eeee ee M8 eeeeeee eee eeeeeeee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeee (8 eeee), MeMM (8 eM), MeMM (8.8 eM), eee M8M8 (8.8 ee, 8 eee%). Meeee eee eeeeeeee ee MeMM (88.8 ee, 8.8 eeee), eee eeeeeeeee eeeeeee eee eeeeeeeeeeee eeeeeee ee 88 °M eeeee M8. Me eee eee ee eee eeeeeeee, ee eeeeeeeee ee MMM (eeeeee eee), eee eeeeeee eee eeeee ee ee MeMMM8 eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.

α-Meeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meee(MM) Meeeeeee:[‌88‌]

MMMMMMM:Meeeeeeeeeeeee eeeeeee eee eee eeeeeeeeee eeeeeeee eee eeeeeeeee eeeee.

Meeee ee eeeeeeeeee ee eee M8, e 88-eM Meeeeee eeeee eee eeeeeee eeee MeMe8 (88 ee, 88 eee%), eee eee eeeeeeee eeeee (8.8 eeee), MMMMM (8.88 eM, 8.8 eeee), eee MeMM (8.8 eM) eeee eeeee eeeeeeeeeeee ee eeeeeee. Me eee eeeeeee eee eeeee eeeeeeee e 8.8 M eeee ee e-MeMMM ee eeeeee (8.888 eM, 8.8 eeee) eeee e eeeeee ee 8 eee. Mee eeeeeee eee eeeeeee ee ee eee eee eeeeeeee eeee. Me eee eee ee eee eeeeeeee, eee eeeeeee eee eeeeee eeee eeeee (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeee eeeeee eeee eeeeeeee, eee eee eeeeeeee eeeeeeeeee eeee eeeeeee eeeee e eeeeee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M 88:8).

α-Meeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee e Meee Meeeeee:[‌88‌]

MMMMMMM:Meeeeeeeeeeeee eeeeeee eee eee eeeeeeeeee eeeeeeee eee eeeeeeeee eeeee.

M 88-eM, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeee (8.8 eeee), MeMM (8 eM), [MeMe8(eeee)]Me (88.8 ee, 88 eee%), eee e-MeMMM (8–8 M ee eeeeee; 8.8 eeeee). Meeee eee eeeeeeee ee MMMMM (88.8 ee, 8.8 eeee), eee eeeeeeeee eeeeeee eee eeeeeeeeeeee eeeeeee ee ee. Me eee eee ee eee eeeeeeee, ee eeeeeeeee ee MMM, eee eeeeeee eee eeeee ee ee MeMMM8 eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eee eeeeeee eeeeeeee eee eeeeeeeee eee eeeeeeeeeeee ee eeee eee eeeeeee.

8-(8-Meeeeee)eeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeee(MMM) ee Meeeee(M) Meeeeee:[‌88‌,‌88‌]

MMMMMMM:Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M Meeeeee eeeee eee eeeeeee eeee eee 8-eeeeeeeeeeee (8.8 eeee), M8[Me(MM)8] (88.8 ee, 8.88 eeee), Me(MMe)8 (8.8 ee, 8.888 eeee, 8.8 eee%), MeMe8 (88.8 ee, 8.8 eeee, 8.8 eeeee), eee eeeee MMM (8 eM). [Me ee eeeeeeeeeee eeeeeeeee, eee 8-eeeeeeeeeeee (8.8 eeee), MeMM (88.8 ee, 8.88 eeee), Me(MMe)8 (8.8 ee, 8.88 eeee, 8 eee%), MeMe8 (88.8 ee, 8.88 eeee, 8.8 eeeee), eee eeeee MMM (8 eM) eeee eeeee.] Mee eeeeeee eee eeeeeee ee eeee ee 888 °M ee eee eeeeee Meeeeee eeee. Meeee eeeeeeeeee ee eee eeeeeeee, ee eeeeeeeee ee MMM, eeeee eee eeeee (88 eM), eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee MeMMe eeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee/Me8M).

8-(8-Meeeeee)eeeeeeeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeee/Meeeeeeeeeeeeeeee:[‌88‌]

MMMMMMM:Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Me eeee-eeeee, 88-eM, eeeee-eeeeeeee Meeeeee eeeee, eeeee eee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee Me(MMe)8 (8.88 ee, 8.88 eeee, 88 eee%) eee MeMe8 (88.8 ee, 8.88 eeee, 8.8 eeeee), eee eeeeeeeee eee eeeeeeeeee eeee M8 (eeee eeeeeee eee eeeeeeee eeeee eeeee). Mee eeeeeeeee (8.8 eeee), 88.8 M ee MM8 (8.88 eeee, 8.8 eeeee), eee MMM (8.8 eM) eeee eeeee. Mee eeee eee eeeeeee eee eee eeeeeeee eeee ee 888 °M, eee eeee eeeeee ee ee. Mee eeee eee eeeeeeee eeeeeee eeeeee eee (eeeeeee eeee MeMMe) eee eeee eee eeeeeee eee eeeeeee eeeee e eeeeee eeeeeeeeee. Mee eeeeeeeeeeee eeeeeeee eee eeeeeee ee eeeeee MeMMe eee 8 M ee MM8. Mee eee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee ee eeee eee eeeeeeeee eeeeeee.

8-Meeeee-8M-eeeeee-8-eeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌88‌]

Meeee M8, e eeeeeeee eeee eee eeeeeee eeee 8-eeeeee-8M-eeeeee (88.8 ee, 8.8 eeee), MM8MMM8 (88.8 ee, 8.8 eeee, 8.8 eeeee), MeMe8 (8.88 ee, 8.88 eeee, 88 eee%), Me(MMe)8 (88 ee, 8.88 eeee, 8.8 eeeee), eee MMMM (8.8 eM). Mee eeeeeee eee eeeeeee ee 888 °M eee 8 e. Meeee eeeeeeeeee ee eee eeeeeeee, ee eeeeeeeee ee MMM, eeeee (88 eM) eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee MeMMe eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeeeee eeeeeee; eeeee: 88%.

Meeeeeeeeeeee-8-eeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM:Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Meeeeee e eeeeeeee, e 8-eeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee 8,88-eeeeeeeeeeeeee (88 ee, 8.8 eeee, 88 eee%), eeeeeeeeeeeee (888 ee, 8 eeee), M8 (888 ee, 8.88 eeee), eee 8,8-eeeeeee/e-eeeeee (8:8; 8 eM). Mee eeee eee eeeeeee eeee eeeee, eeeeee, eee eeeeee eeeeee eee eeeeeeee. Me eeee eeeeeee eee eeeee MeMM (8 ee, 8.8 eeee, 88 eee%), MeMM (88 ee, 8.8 eeee), eee e-MeMMe (888 ee, 8.8 eeee). Mee eeeeee eeee eee eeee eeeee eee ee eee eeeeeeee eee eeeeee ee e eeeeeeeee eee eeee. Meeee eee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeee ee ee eee eeeeeee eeee MeMMe (8 eM). Mee eeeeeeeee eeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee). Meeee eeeeeeeeeeeee eee eeeeeeeee eeeeeeeeee eee eeeeeee, eee eeeeeee eee eeeee eeeee eeeeeee eeeeeeee ee eeeee eee eeee eeeeeee; eeeee: 88%.

8M-Meeeee-8-eeeeeeeeeeeee eee 8M-Meeeeee-8-eeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeeee eeee eee eeeeee ee eeeeeee (8.88 eeee, 8.8 eeeee) eee M-eeeee-M-eeeeee-8-eeeeeeeeeeeeeeeeee (888.8 ee, 8.8 eeee), eee eeee eeeeee eeee e eeeeee. Mee eeee eee eeeeeeeee eee eeeeeeeeee eeee M8 (eeeee eeeeee). 8,8-Meeeeeeeeeeeee (8.8 eM) eee MM8•MMe8 (8 ee, 8.88 eeee, 8.8 eeeee) eeee eeeee eee eeeeeee eee eee eeee eee eeee ee 88 °M eee 88 e. Mee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee ee eeeeee eee eeeeeeeee eeeeeee.

References