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19.5.6.1 Method 1: Substitution of a Hydroxy Group in a One-Pot Procedure

DOI: 10.1055/sos-SD-019-00137

Subramanian, L. R.Science of Synthesis, (200419197.

Augmentation by one carbon atom occurs when an alcohol is transformed into a nitrile, and this process often commands great importance in organic synthesis. The functional group interconversion of a hydroxy group into a nitrile involves an intermediate alcohol derivative and can be carried out in one pot by various methods. A modified Mitsunobu reaction[‌1‌] has been applied to the conversion of octadec-9-en-1-ol (1) into nonadec-10-enenitrile (2) using anhydrous lithium cyanide in combination with a preformed complex of diethyl azodicarboxylate/triphenylphosphine (Scheme 1).[‌2‌] Acetone cyanohydrin (2-hydroxy-2-methylpropanenitrile) can be used in place of lithium cyanide for the preparation of alkyl cyanides 4 from alcohols 3; however, in some cases steric hindrance reduces the yields of the products (Scheme 2).[‌3‌] The alcohols probably react via an SN2-type displacement of an intermediate alkoxyphosphonium species to give the nitriles.

Meeeee 8 Meeeeeeee ee Meeeeee-88-eeeeeeeeee ee e Meeeeeee Meeeeeeee Meeeeeeee Meeee Meeeeee Meeeeee[‌8‌]

Meeeee 8 Meeeeeeeeee ee Meeee Meeeeeee eeee Meeeeeee ee e Meeeeeee Meeeeeeee Meeeeeeee Meeee Meeeeee Meeeeeeeeee[‌8‌]

Mee eeeeeeeee eeeee eeeeeee eeeeeeeeeee[‌8‌] eeeeeeee eee eeeeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeeeee eee eeeeeee eeeeeeeeeee ee e eeeeeeee ee eeeeeeeeeeeeeeeeee eee eee eeeeeee. Meeee eeeeeeee eee 88 eeeeeee, eeeeeee eeeeeeeeeee ee eeeee. Mee eee eeeeeeeeeee ee eeeeeeeeeee eeeeeeee, eee eeeeeeee ee eeeeeeee eee ee ee eeeeeee eeeeeeee ee eeeeee eeeeeeeeeee eeeeee; eeeeeee eeeeeeeeeeeeeeeee, eee eeeeeee, eee eeeeeee eeeeeeeeeee eee eeeeeeeeeeee eeeee ee e eeee eeeeeeee ee eeeeeeeeeeeeeeeeee ee eeeeeee eeeee, ee ee eee eeee eee eee eeeeeeeeeee ee (8M,8M)-eeee-8,8-eeeeeeeeeeee (8) eeee eee eeeeeeeeeee eeeeeee 8 (Meeeee 8).[‌8‌] Meeeeee eeeeeeeee ee eee eeeeeeee eeeeeeee ee eeeeeeee ee eeeee eeeeeeeee ee eeeeee eeeeee eeeeee ee eeeeeeeee eeeeeeee eeee eeeeeeeee eeeeeeee.[‌8‌] Meeeeee eeeeee, e.e. 8, eee eeee eeeeeeeeee eee eeeeeeee, e.e. 8, ee eeee eeeeee, eeeee eeee e eeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeeee ee eeeeeee: eeeeeee eeeeeeeeeeeeeeeee ee eeeee ee e eeeeeeee ee eeeeeeeeeeeeeeeeee ee eeeeeee eeeee, eeee eee eeeeeee ee eeeee eeeeeeee ee eeeeeee eeeeeeeeeee (Meeeee 8).[‌8‌] Mee eeeeee ee eee eeeeeeee eee eeeeeeeeee eeeeeeee α-eeeeeee eeeee eee eeeeee, eee α-eeeeeee eeeeeeee eee α-eeeeeee eeeeeee eeeeeeeee eeeee eeeee eeeeeeee eeeeeeeeee.

Meeeee 8 Meeeeeee Meeeeeeee Meeeeeeeee ee Meeeeeee eeee Meeeeeee eeee Meeeeee Meeeeeeeeee[‌8‌‌8‌]

Meeeeeee, eee eeeee ee Meeeeeeee eeeeeeeee eeee eeee eeeeeeeeee, eeeeeeeeeee eee eee ee eeeeeee eeeeeeeeeeeeeeee. Mee eeeeeeeeeee ee M,M,M,M-eeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM) eee eeeeeeeeeeeeeeeee ee ee eeeeeee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee 8 eeee eeeeeee eeeeeeeeeee ee eeeeeee eeeeeeee 88 (Meeee 8).[‌8‌] Meeeeeee eee M,M,M,M-eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeee ee eeeeee, eee eeeee eee eeeeeeeee, eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM) eee eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM), eee ee eeee ee eeeeee e eeeeee eeeeeeee, eeeeeeeeee ee eee eeee ee eeeeeeeee eeeeeeee. Mee eee eeeeeeee eeeee eeee eeee eeeeeee eee eeeeeeeee eeeeeeee (8.8eee eeeee) eee eeee eeeeee eeeeee eeee eeeeeeeee eeeeeeee (8eee eeeee) eeee eeeee eeeeeeee eeee eeee eeeeee eeeeeeeee.[‌8‌‌8‌] Meeeeee eeeeeeee eee ee eeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeeee eeeee, eee eeeeee eeeeeeeee eeeeee eee MM eeeee ee eee eeeeeeeee eeeeeee eeeeeeeee eeeeeeeee ee eee eeeeeee eeeeeee eeeee (Meeee 8, eeeee 8). Meeeeeeee ee 8β-eeeeeeeeeee eeee eeeeeee eeeeeeeeeee eeee eee eeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM) eeeee e eeee eeeee ee 8α-eeeeeeeeeeeeeee eeee eeeeeeee Meeeee eeeeeeeee.[‌8‌]

Meeee 8 Meeeeeeee ee Meeeeee eee Meeeeeeee Meeeeeee Meeeeeeee ee Meeeeeee Meeeeeeee Meeeeeee Meeee M,M,M,M-MeeeeeeeeeeeeeeeeeeeeeeeeeeMeeeeeeeeeeeeeeee[‌8‌]

Meeee M8 Meeeeeee Meeeeeeeee Meeee (%) Mee
8 (MM8)88Me eeeeeee eeeeeeeeeee, MMMMMe8M, eeeeeee, ee, 88e 88 [‌8‌]
8 eeeeeee eeeeeeeeeee, MMMMMe8M, eeeeeee, ee, 88e 88 [‌8‌]
8 eeeeeee eeeeeeeeeee, MMMMMe8M, eeeeeee, ee, 88 ee 88 [‌8‌]
8 eeeeeee eeeeeeeeeee, MMMMMe8M, eeeeeee, ee, 88e 88 [‌8‌]

e 8 Meeeeeeeeee ee eeeeeee eeeeeeeeeee eee MMMMMe8M eeee eeee.

M eee-eeee eee-eee eeeeeeeee eee eee eeeeeeeeeeeeee ee eeeeeee eeeeeeee 88 eeee eeeeeeee 88 eee eeeeeeeeeeeeeeeee eeeeeeee eeee eeeeee. Mee eeeeeee ee eeeee eeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee eee, eeeee eeeeeeeeeee eee eeeeeeeeeeeeeee eeee eeeeee, eee eeeeeee ee eeeeee eeee eeeeee eeeeeee ee e 8:8 eeeeeee ee eeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeee eeeeeeeee.[‌8‌] Meeeeeeeeeeee, eeee 88 [M8=(MM8)8MM] eee e ω-eeeeeeeeeeeee 88 [M8=(MM8)8Me] eee eeeeeeeee eeee eeeeeeeeee, eeeeeeee eeeeee ee eee eeeeeeeeee eee eeee eeeeeeee ee eee eeeeeeeeeeeeee (Meeeee 8).

Meeeee 8 Meeeeeeee ee Meeeeeee eeee Meeeeeee eee Meeeeeeeeeeeeeeee[‌8‌]

Mee eee-eee eeeeeeeeeee ee eeeeeeee eeee eeeeeeeee eee ee eeeeeeee (Meeeeee 88.8.8.8.8), eeeeeeeee ee eeeeee(MM) eeeeeee eee eeeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeee, eee eeee eeee eeeeeeee ee eeeeeeee eee eeeeeee eeeeeeee; eeeeeeee 88 eee eeeee eeeeeeee ee eee eeeeeeee eee eee eeee eeeeeeeee eeee eeeeeeee 88 eee ee eeeeeeee (Meeeee 8).[‌8‌] Meeeeee, eee eeeeeeee ee eeeeeee ee eeeeeeee eee eeeeeee eeeeeeee.

Meeeee 8 Meeeeeeee ee Meeeeeee eeee Meeeeeee ee Meeeee(MM) Meeeeee/Meeeeeeee Meeeeeeeeeeeeee ee Meeeeee[‌8‌]

Meeeeeee eeeeeeeeee ee eeeeeee eeeeeeee 88 eeee eeeeeeee 88 ee eeeeeeee eeeee eeeeeeeeeeeeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeee eeee eeeeeeee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eeeeeee [Me(MMM8)8Me(MMM8)8] eeeee eeeeeee eeeeeeeee eeeeeeeee ee eeeeee-8-ee (Meeeee 8).[‌88‌] Meeeeee eeeeeeeee, eeeeeeee, eee eeeeeeeeeeee eeeeeeee eee ee eeeeeeeeeee eeee eeeee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeeee. Mee eeeeeeee eeeeeeeeee eeeeeeee eee eeeeeeee ee eeeeee eeeee, eeeeeee, eeeeeeeee, eee eeeeeeeeeeeee eeeeee ee eeeeeeee eeeeeeee.

Meeeee 8 Meeeeeeee ee Meeeeeee eeee Meeeeeee ee Meeeee-Meeeeeeee Meeeeeeee eeee Meeeeeeeeeeeeeeeee Meeeeeeeeeeeeee ee eee Meeeeeee ee Meeeeeee Meeeeeee Meeeeeeee[‌88‌]

Meeeeeeee eeeeeeee, eeeeeee, eee eeeeeeeeeee eeeeeeee 88 eee ee eeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee 88 ee eeeeeeeee eeee eeeeeeeee(MM) eeeee eee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeee-8-ee/eeeeeeeeeeeeeee.[‌88‌] Meee ee ee eeeeeeeee ee eee eeee ee eeeeeeee eeeeeeeee eeeee eee eeee eeeeeeeeee (Meeeeee 88.8.8.8.8.8).[‌88‌] Mee eeeeeee ee eeeee eeeeeeee ee eeee ee eeeeeeeee(MM) eeeee ee ee eeeeeeee, eeeee ee eeee eeeeeeeee eeee eee eeeeeee eee eee eeeeeeee (Meeeee 8).

Meeeee 8 Meeeeeeeee ee Meeeeeee eee Meeeeee Meeeeeee eeee Meeeeeee Meeee Meeeeeeee(MM) Meeee/Meeeeeeee Meeeeee ee eee Meeeeeee ee Meeeeee[‌88‌]

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

Meeeee 8 Meeeeeee ee 8-Meeeeee-8,8-eeeeeee-8M-8-eeeeeeeeeee eee e Meeee eeee Meeeeeeeeeeeee Meeeeee ee eee Meeeeeee ee Meeeeeee(MM) Meeeeeee[‌88‌]

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

Meeeee 8 Meeeeeeee ee 8-Meeeeeeeeeeeeeee-8M-eeeee-8-ee Meeeeee[‌88‌]

Meeeeeeeee 88, eeeeeeee eeee eeeeeeeee eeeeeeeee ee eeeeeeeee eeee eeeeeeeeee eeeeeeeeee eeeee eeeee eeeeeeeeeee eeeeeeeee, eee eeee eeeeeeeee eeee eeeeeeee 88 eeee eeeeeeeee eeeeeee ee eeeeeeee eeeeeeeee (Meeeee 88).[‌88‌] Mee ee eeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeeeee(MM) eeeeeeee eeeee eeeeee eeee eeeeeeee eeeeeeeeee (e.e., 88, M8=eeee), eeeeee eee 8-eeeeee- eee 8-eeeeeeeeee eeeeeeeeeeee eeeee eeee eee eeeeeeeeeeeee α-eeeeeeeeeeeee 88 ee 88 eee 88% eeeeee, eeeeeeeeeeee. Mee eeeeeeeeeeeeee eeeeeee/eeeeeeee(MM) eeeeeeee eeeeeee eee eeee ee eeee eee eee eeeeeeeeee ee eeeeeeeeee 88 (eeeee eeee eeeeeeeee eeeeeeeee) eeee eeeeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeee ee Meeeeeeeee eeee Meeeeee Meeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee Meeeeeee 8; Meeeeee Meeeeeeee:[‌8‌]

MMMM (8.8eeee) eee eeeee eeeeeeee eeeee M8 eeee eeeeeeee ee e eeee ee Me8M (8.8eeee) eee eeeeeee 8 (8eeee) ee eee Me8M (8eM) ee 8°M. Meeeeeee eee eeeeeeeee eee ee eeeeeeeeee 88eee eeeeee eeeee eeee e eeeee eeeeeeeeeee eeeeee. Meeeeee eeeeeeeeeee (8.8eeee), eeeeeeeee ee Me8M (8eM), eee eeeeee eeeee eeeeeeee, eeeeeee eeeeeeeeeee ee eee eeeee eeeeeeeeeee. Mee eeeeeeee eee eeeeeee ee 8°M eee ee eeeeeeeeee 8eee. Mee eeeeeee eeee eee eeeeeee eee eeeeeeee eee eeeeeeeee ee ee. Meeee ee. 88eee, e eeeee eeeeeeeeeee eeeeeee ee eeee. Mee eeeeee ee eee eeeeeeee eee eeeeeeee ee MMM eeeeeeee. Mee eeeee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee eee) ee Meeeeeeee eeeeeeeeeeee eeeeeeee eee eeee eeeee eeeeeee.

Meeeeee eee Meeeeeeee Meeeeeee 88; Meeeeee Meeeeeeee:[‌8‌]

M,M,M,M-Meeeeeeeeeeeeeeeeeeeeeeeeee (8.8eeee) eee Me8M (8.8eeee) eeee eeeee eeeeeeeeeeeee ee e eeee ee eeeeeee 8 (8eeee) eee eeeeeee eeeeeeeeeee (8.8eeee) ee eee eeeeeee (MMMMMMM: eeeeeeeeee) eeee eeeeeeee ee ee eeeee eeeee. Meeeeeee eee eeeeeeeee eee 88e. Mee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM) ee eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM) e eeeeee eeeeeeeeeee eee eeeeeeee; eee eeeeeeee eee eeeeee ee ee Mee eeeeeeee eeee eeeee eeeeeee eeeeeeeeeeee eeeee ee eeeee eeeeeeeeee. Mee eeeeeee 88 eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee), eeeee eeeeeee eeeeee ee eee eeeeeeee eeeeeeee ee eeeeeeeeee eeee ee eeeeeee eeeeeee eee eeeeeeeeeee ee eee eeeeeee ee eeeee.

(88M)-Meeeeee-88-ee-88-eeeeeeeeee [88, M8=(MM8)8MMMM=MMMe]; Meeeeee Meeeeeeee:[‌8‌]

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

MMMMMMM: Meeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeee eeeee eeeeeeeeee eee ee eee eee eeee eeeeeeee.

Me e eeee ee (88M)-eeeeeeee-88-ee-88-ee-8-ee [88, M8=(MM8)8MMMM=MMMe; 888ee, 8.88eeee] ee eee MM8Me8 (8eM) eee eeeee MMMM (888ee, 8.88eeee). Mee eeeeeee eee eeeeeee eee 88eee ee ee. Mee MMM eeeeee, eeeee eeee eee eeeeeee, eee eeee eeeeeeeeee, eee eee eeeeeee eee eeeeeee eeee eee MMMM (8eM) eee eee MMM (8eM) eee eeeeeee eeee eeeeeeee MeMM (888ee, 8.88eeee), eeeeeeeeee eeeee ee 888°M/8.8Meee eee 8e. Mee eeeeeee eee eeeeeeee eeeee M8 eeeee ee eeeeeeeeeeeeeeee eee eeeeeeee (MM eeeeeeee). Mee eeee eeeeeeee MMM eee eeeeeeee eee eeeee eeeeee, eeeee eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eee eeeeeee eee eeeeeeeeee ee eeeeee e eeeeeee eeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/Me8M 8:8) ee eeee eee eeeee eeeeeeee; eeeee: 888ee (88%).

Meeeeeeeeeee (88, M8=Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeee eeeeeee (88, M8=Me; 88.8e, 888eeee), eeeeeeeeeeee eeeeeee [Me(MMM8)8Me(MMM8)8; 8.8e, 8eeee], MM8MMM8 (8.8e, 888eeee), (Me8M)8M8M8 (88.8e, 888eeee), eMeMM (888eM), MMM (8.8e, 888eM), eee M8M (888eM) eee eeeeeeeeee eeeeeee ee 88°M eee 8.8e. Mee eeeeeee eee eeeeeee eeee Me8M (888eM), eee eee eeeeeeeee eeeeeeeee eeee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeee eeee eeeee (8×88eM) eee eeeee (MeMM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeee eeeeeee, eeeee ee eeeeeeeeeeee eeeeeeee eee eeee eeeeeee; eeeee: 8.8e (88%).

8-Meeeeeeeeeeeeeeee (88, M8=8-MeM8M8); Meeeeee Meeeeeeee:[‌88‌]

M 8M eeee ee MM8 ee eMeMM (8.8eM, 8.88eeee) eee eee MeMM8 (8.88e, 88.8eeee) eeee eeeee ee e eeeeeee eeee ee 8-eeeeeeeeeee eeeeeee (88, M8=8-MeM8M8; 8.888e, 8.88eeee) ee MMM (8.8eM). Meeeeeeee MeM8 (8.88e, 88.88eeee) eee eeeee ee eee eeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88e eee eeee eeeeeee eeee MM8Me8 (88eM). Mee eeeeeee eee eeeeeeee eeeeeee Meeeee, eee Meeeee eee eeeeee eeee eeee MM8Me8, eee eee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee eeeee 8:8) ee eeee eee eeeeeee; eeeee: 888ee (88%); ee 888.8°M.

8-Meeeeee-8,8,8,8-eeeeeeeeeee-8,8-eeeeeee-8M-8-eeeeeeeeee-8-eeeeeeeeeeee (88, M8=M8=M8=Me); Meeeeee Meeeeeeee:[‌88‌]

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

M eeee ee 8-eeeeeee-8,8-eeeeeee-8M-8-eeeeeeeeee 88 (M8=M8=M8=Me; 88e, 88.8eeee) ee MM8Me8 (888eM) eee eeeeeee ee 88°M eeeee MMMMM (88.8eM, 888eeee) eee eeeee ee eee eeeeeee eeeeeeee ee eeeeeeee eeeeeeee ee MeMe8 (88.8e, 888eeee). Mee eeeeeeeee eeeeeee eee eeeeeee eee 8.8e, eeeeee eeeee eeee eee eeeeeeeeeee eee eeeeeee ee eeee ee 88°M. Mee eeeeeeee eee eeeeeeee ee eee eeeeeeee eeeeeeee ee eeeeeeee (888eM) (MMMMMMM: MMM eee eeeeeeeee). Meeee eeeeeeee eee 8eee, eee eeee eee eeeeee eeee eee eeeee (MMMMMMM: MMM eee eeeeeeeee). Mee MM8Me8 eeeee eee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8×). Meeee eeeeeeeeee ee eee MM8Me8 eeeeeee (eeeee eee eeeeeeeeeeee eeeeee eeee eee. MeMMM8 eeee) eeee eee eeeee eeeeeeee ee e eeeee eeeee eeeee eee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8); eeeee: 88.88e (88%); ee 888888°M.

References