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29.6.1.2.3.3 Variation 3: From Alcohols with Removal of Water by Chemical Means

DOI: 10.1055/sos-SD-029-00368

von Angerer, S.; Warriner, S. L.Science of Synthesis, (200729328.

The equilibrium between an aldehyde (or ketone), hemiacetal, and acetal can also be shifted to the acetal side when the water formed during the reaction is removed by a chemical reaction, usually with an ortho ester. The ortho ester, usually an alkyl orthoformate or orthoacetate, is used together with the alcohol required for acetalization. However, the ortho ester can be subject to two different reactions, either undergoing hydrolysis with the water formed to give the normal ester and alcohol or converting the carbonyl compound directly into the acetal 31 (Table 4). Thus, the alcohol component of the ortho ester should be the same as the alcohol used for the acetalization. Generally the same catalysts as for the reactions with removal of water by azeotropic distillation can be used.[‌17‌] They include 4-toluenesulfonic acid,[‌235‌‌241‌] trifluoromethanesulfonic acid[‌242‌] and its bismuth salt,[‌243‌] trifluoroacetic acid,[‌244‌] hydrogen chloride,[‌245‌‌247‌] phosphoric acid,[‌248‌] various ammonium salts,[‌249‌‌255‌] ion exchange resins,[‌256‌‌258‌] lanthanoid chlorides,[‌200‌,‌201‌,‌259‌] iron(III) chloride,[‌260‌] and phosphinerhodium complexes[‌261‌] (Table 4). A hydroxy function in the aldehyde is converted into the formate in parallel to the acetalization.[‌262‌] Strong acids should be avoided because they can decompose the ortho ester during the reaction.[‌263‌] However, it is possible to generate them in situ, as demonstrated by the use of tetrabutylammonium tribromide[‌264‌] or bromodimethylsulfonium bromide[‌265‌] as catalyst. The latter reagent can be used for acetalization under solvent-free conditions.[‌265‌] It is also possible to work under aprotic conditions when decaborane,[‌266‌] 2,3-dichloro-5,6-dicyanobenzo-1,4-quinone,[‌267‌] or N-bromosuccinimide[‌268‌] is used as the catalyst.

Meeee 8 Meeeeeeee ee Meeeeee eeee Meeeeeee Meeeeeeee eee Meeeeeee eeee Meeee ­Meeeeeeeeeeee ee Meeeeeeeeee Meeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌]

Meeee M8 M8 M8 Meeeeeee Meeeeeeeee Meeee (%) Mee
8 (MM8)8MM8 M Me MeMM 88°M, 8.8e 88 [‌888‌]
8 MM=MM8 M Me MM8MM8 ee, 88e 8888 [‌888‌]
8 MM=MMMe M Me MM8MM8 eeeeee, 88eee 88 [‌888‌]
8 8,8,8-(MeM)8M8M8 M Me MM8Me eeeeee, 8e 88 [‌888‌]
8 Me M Me Meeeeeeee MM-888 eeeeee, 8e 88 [‌888‌]
8 MM=MMMe M Me MMe eeeeee, 88eee 88 [‌888‌]
8 MM=MMMe M Me MeMe8(MMe8) 88°M, 8e 88 [‌888‌]
8 (MM8)8MMe M Me MMM 88°M, 88e 88 [‌888‌]
8 (MM8)8MM8Me M Me MeMe8 ee, 88eee 88 [‌888‌]
88 Me M Me MeMe8 ee, 88eee 88 [‌888‌]
88 8-eeeeeee M Me MMe8 ee, 88eee 88 [‌888‌]
88 Me M Me MMM ee, 88e 88 [‌888‌]
88 (MM8)8M(MM8)8 Me MeMM eeeeee, 88eee 88 [‌888‌]
88 (MM8)8 Me MeMe8(MMe8) 88°M, 88eee 88 [‌888‌]
88 (MM8)8 Me MeMM eeeeeeeeee eeeeeeeeeeee ee MMM8Me e [‌888‌]
88 MM8MM8MM8 M Me MeMM ee, 8e 8888 [‌888‌]
88 8-M8MM8M8 8-M8MM8M8 Me MeMM eeeeee, 8e 88 [‌888‌]
88 (MM8)8Me Me Me MMM ee, 8.8e 88 [‌888‌]
88 (MM8)8Me Me Me MMM MM8Me8, ee, 8e 88 [‌888‌]
88 8-MM8M8 8-MM8M8 Me Me(MMe)8 eeeeee, 88e 88 [‌888‌]
88 Me Me Me Me8M+Me8 ee, 88eee 88 [‌888‌]
88 (MM8)88Me M Me Me8MMe+Me ee, 88eee 88 [‌888‌]
88 8-MMM8M8 M Me M88M88 ee, 8eee 88 [‌888‌]
88 Me M Me M88M88 ee, 8eee 88 [‌888‌]

e Meeee eee eeeeeeee.

Meee eeee eeeeeeee eee eeeeee eeeeeeeee eee eeeeeee ee eee eeeeeeee eeeeeeee, eee eeeeee eeeee eeeeeeeee eeeeee eeeee, eeeeeeee eeeeeeeee eeeeeeeeee ee eeee eeeee.[‌888‌,‌888‌] Me eeeeeeee, eeeeee eeeeeee eeeee eeeeee eeee eeeeee eeeeeeeee ee eee eeee eeeee.[‌888‌] Meee α,β-eeeeeeeeeee eeeeeee eeeee eeee eeeeeeee, eeee eeeeeeeeeeeee eee eeeeeeee eeeeee eee M=M eeee eee eeeee, ee eeeee ee eee eeeeeeee ee 8-eeeeee-8-eeeeeeeeeeeeeee-8-eeeee eeee eeeeeeee (Meeeee 88).[‌888‌] Meee eeeeeeee ee eee eeeeee eeee eeeee ee eeeeee ee eee eeeeeeee eeee. Meee α,β-eeeeeeeeeee eeeeeeeee eeee ee eeeeeeee[‌888‌,‌888‌] ee eee-8-eeee[‌888‌] eeeee eeee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eeeee, eeee eee eeeeeee eee eeeeee eeeeeee eee eeeeeeeee eeeeeeee ee eeeeeee eeeeee eee M=M eeee.

Meeeee 88 Meeeeeeeeeeee Meeeeeeeeee ee eee Meeeeeee ee Meeeeee eeeeee e M=M Meee[‌888‌]

Meeeeeee ee eeeeee-8,8-eeeee eeee eeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeeeeee eeeeeeee e eeeeeeeee eeee ee eeeeee: eeee eeeeeeee eeeeee eeeeee eeee ee e eeeeee eeeeee eeeeeeee eeeeeee.[‌888‌,‌888‌‌888‌] Meee eeeeee eeeeeee eee eeeeeeeee eeeee eeee eeeeeeeeeee, eeeeeeeee eeeeeeeeee ee eeeeeee eeeeeeeeeeee eeeee ee eeeeeeee, e eeeeeeeeeee eeeee eeeeeeeeeee eeee eeeeeeeeeee eeeeeeeee eee eeeeeee eeeeeeeeee eeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeee ee Meeee ee Meeeee Meeeeeeee[‌888‌]

Meeeeeeeeeeeeeeeee eee eeee eeeeee eee eeeee eeeeee eeeeee eeeeeeeeeeeee.[‌888‌‌888‌] Meee eeeeeeeee-8-eeeeeeeeeeee eeeeee eeee e eeeeeee ee eeeeeeeeeeeeeeeee eee eeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeeeee eeee, eee eeeeeeeeeeeee eeeeee ee eeeeee ee 88% eeeee.[‌888‌]

Meeee eeeeeee eeeeeeeeee, eee eeeee eeeeee eeeeee eee eeeeeeeeeeeee eeeeeeee eee ee eeeeeee ee eee eeeeeeee ee eeeeeee eeeeee, eeeee eeeeee eeeeeeeeee eeeeee ee eeeee e eeeeeeee eeeeeeee eeeeeeeee eeee eee ee eeeeeeeee eee, eeeeeee eee eeeeeee eeeeee 88 (Meeee 8).[‌888‌‌888‌] Me eeeeeee ee eee eeeeeeeeeee ee 8-eeeeee-8,8-eeeeeeeeeeeeeee eeee eeeeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee 8-eeeeeeeeeeeeeee eeee eee 8,8-eeeeeeeeeeeeeeee, eeeee eeeeeeeeee ee eeeeeee ee eee eeeeee ee eee eeeeeeee eee ee eeeeeeeeeeee eeeeeee.[‌888‌] Meeeeeeee ee eee eeeeeee eeeeee ee eee eeeeeeee eee eeeeeee eeeeeeee, eeeeeeee eeeeeeeeeee ee eeeee eeeeeee eee eeeeeeee.[‌888‌]

Meeee 8 Meeeeeeee ee Meeeeee eeee Meeeeeee Meeeeeeee eee Meeeeeee Meeee 8,8-Meeeeeeeeeeeeeee, Meeeeeee Meeeeee, ee Meeeee Meeeeeeeeee ee Meeeeeeeeee Meeee[‌888‌‌888‌,‌888‌]

Meeee M8 M8 M8 Meeeeeeeee Meeee (%) Mee
8 Me Me Me Me8M(MMe)8, MeMM, eeeeee, eeeeeeeeeeee ee 8888°M 88 [‌888‌]
8 (MM8)8 Me Me8M(MMe)8, MeMM, eeeeeee, eeeeeeeeeeee ee 8888°M 88 [‌888‌]
8 (MM8)8 MM8MM=MM8 Me8M(MMe)8, MeMM, eeeeeee, eeeeeeeeeeee ee 8888°M 8888 [‌888‌]
8 (MM8)8MMMe(MM8)8 8-M8MM8M8MM8 Me8M(MMe)8, eeeeeeeeeee-8-eeeeeeee eeee, eeeeeee, ­eeeeeeeeeeee ee 88°M, 8e 88 [‌888‌]
8 8-M8MM8M8 M 8-M8MM8M8MM8 Me8M(MMe)8, eeeeeeeeeee-8-eeeeeeee eeee, eeeeeee, ­eeeeeeeeeeee ee 88°M, 8e 88 [‌888‌]
8 (MM8)8MM8Me M Me Me8M(MMe)8, MMe, MeMM, eeeeee, 8e 88 [‌888‌]
8 (MM8)8 Me eeeeeeee eeeeeee, MMe, MeMM, eeeeee, 8e 88 [‌888‌]
8 Me M Me MeMM8, eeeeeeeeeeeeeee, MeMM, ee, 888eee eeeee [‌888‌]

e Meeeeeeeeeeeee = M8MeM88M88·eM8M ee M8MMe88M88·eM8M.

Meeeeee eeeee ee eeeeeeeee eeee eee ee eeee eee eee eeeeeeeeee eeeeeee ee eeeee eee eeeeeee eeeeeeee, eeeee eee eeeeeeeeeeee eeeeeee ee eeeee eeeeee eee eeeeeee. Meee eeeee eeee eeeee ee eeee eeeeee eeeeeee eee eee eeeeeeeee ee eee eeeeeeeeee eeeeeee; eeee eeeeee ee eeeeeeee eeee ee eeeeeee eee(eeeeeeeeeeeeeee)eeeeeee.[‌88‌,‌88‌,‌888‌‌888‌] Meeeee eeeeeeeeeee eee eeee eeee eeee ee eeeeee eeeee eeee eeeeeeeeeeeee eeeeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee Meeeeee 88 (M8=Me; e.e., Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee M-Meeeeeeeeeeeeeee eeee Meeeeeeeeeeeeee:[‌888‌]

Me e eeee ee eee eeeeeeee eeeeeeee (8eeee), MM(MMe)8 (8.888eeee), eee eee MeMM (88eeee) ee MM8Me8 (88eM), eee eeeee MMM (8.888.88eeee) eee eee eeeeeeeee eeee eee eeeeeee ee ee. Meeee eeeeeeeeee ee eee eeeeeeee (ee MMM ee MM), eeee 88% ee MeMM (88eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 88eM) eee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeee eeee eeeeeee. Meeeeee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8888%.

Meeeeee Meeeeee 88 (M8=Me; e.e., Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee M-Meeeeeeeeeeeeeee eeeeeee Meeeeeeeeeeeeee:[‌888‌]

Me e eeee ee eee eeeeeeee eeeeeeee (8eeee) eee MM(MMe)8 (8.888.8eeee) ee eee MeMM (88eM), eee eeeee MMM (8.888.88eeee) eee eee eeeeeeeee eeee eee eeeeeee ee ee. Meeee eeeeeeeeee ee eee eeeeeeee (ee MMM ee MM), eeee 88% ee MeMM (88eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 88eM) eee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeee eeee eeeeeee. Meeeeee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8888%.

8,8-Meeeeeeee-8-eeeeeeeeeeee [88, M8=(MM8)8MM8; M8=M; M8=Me; Meeee 8, Meeee 8]; Meeeeee Meeeeeeee Meeee 8-Meeeeeeeeeeeeee Meee:[‌888‌]

Meeeeee eeeeeeeee 8-eeeeeeeeeeeee (8.888e, 88eeee) ee MeMM (8eM) eee eeeeeee eeee MM(MMe)8 (8.888e, 88eeee) eee MeMMM8M (88ee). Mee eeeeeee eee eeeeeee, eeee eeee ee ee eee 8.8e (eeeeee eeeeee eeee). Meeee eeeeeee ee eeeeeeeee ee e eeeeee eeeeeeeeee ee ee. 88°M, eee eeeeeeeee eeeeee eee eeeeeeeeeee eeee eee. MeMMM8 eeee (88eM). Mee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88eM) eee eeeee (MeMM8) eee 8e, eee eee eeeeeee eeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eeeee eeeeee eeeeee. Meeeeeeee eeeeeeeeeeee eeee e eeeeeeeee eeeeee; eeeee: 8.888e (88%); ee 88°M/88Meee.

8,8-Meeeeeeeeee-8-eee (88, M8=MM=MMMe; M8=M; M8=Me; Meeee 8, Meeee 8); Meeeeee Meeeeeeee Meeee Meeeeeee Meeeeee:[‌888‌]

Me e eeee ee (M)-eee-8-eeee (88.8 e, 8.88 eee) ee MM(MMe)8 (88 e, 8.88 eee) eee eeeee MM8MM8 (8.8 e) ee MeMM (88 eM), eee eee eeeeeee eee eeeeeeee eee 88 eee. Mee eeee eeeeeee eee eeeeee, eeeeeeee, eeeeeee eeee Me8M, eee eeeeee eeee eeeeeee eee M8M. Mee eeeee Me8M eeee eee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeee eee eeeeeee ee e eeeeeee eeeeee eeeeee; eeeee: 88 e (88%); ee 88°M/88 Meee.

Meeee 8,8-Meeeeeeeeeeeeeeeee [88, M8=(MM8)8MM8Me; M8=M; M8=Me; Meeee 8, Meeee 8]; Meeeeee Meeeeeeee Meeee Meeeee(MMM) Meeeeeee:[‌888‌]

Meeeeee eeeeeeeee MM(MMe)8 (888eM, 8.88eee) eee eeeee ee e eeee ee eeeee 8-eeeeeeeeeeee (88.88e, 888.8eeee) eee MeMe88M8M (88.8e, 888eeee) ee MeMM (888eM) ee ee. Meeee 88eee, eee eeeeeeee eee eeeeeeee eeee eee. MeMMM8. Mee eeeeeee eee eeeeeeeee eeee Me8M (8 ×) eee eee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee eeeeeeee eee eeeeee ee ee eee; eeeee: 88.8e (88%); ee 8888°M/8Meee.

(Meeeeeeeeeeeee)eeeeeee (88, M8=Me; M8=M; M8=Me; Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee 8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee:[‌888‌]

Me e eeee ee MeMMM (8.88e, 88eeee) eee MM(MMe)8 (8.88e, 88eeee) ee eee MeMM (88eM) eee eeeee MMM (88.8ee, 8.8eeee) eee eee eeeeeeeee eeee eee eeeeeee ee ee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Meeee eeeeeeeeee (88e), eeee eee. ee M8MM8 (88eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeee eeeeeeee eeee eeeeeeeee eee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eee eeee eeeeee; eeeee: 8.88e (88%).

Meeeeeeeeeee(8-eeeeeeeeeee)eeeeeee (88, M8=M8=8-M8MM8M8; M8=Me; Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeeeeeeeeeeee Meee:[‌888‌]

Me e eeeeeee eeee ee 8,8-eeeeeeeeeeeeeeeeeee (8.88e, 8.8eeee), MM(MMe)8 (8.88e, 88.8eeee), eee MeMM (8.88e, 88.8eeee) ee MeMM8 (88eM), eeeeee ee ee eee-eeeee eeee, eee eeeee MeMM (888ee, 8.8eeee) eeeeeeee. Mee eee eeee eee eeeeeeee ee ee eee eeee eee eee eeee eee eeeeeeee eee 8e. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee eee. MeMMM8 eeee (88eM). Mee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88eM) eee eee eeeeeee eeeee eee eeeee (MeMM8). Meeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeeeeeee e eeeee eeeee, eeeee eee eeeeeeeeeeeeee (88% MeMM); eeeee: 8.8e (88%); ee 888°M.

Mee(8-eeeeeeeeeeee)eeeeeeeeeeeeeeee (88, M8=M8=8-MM8M8; M8=Me; Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee Meeeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeee:[‌888‌]

M eeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeee (8.88e, 8.88eeee) ee MeMM (8eM) eee MM(MMe)8 (8.88e, 88.8eeee) eee eeeeeee ee ee ee Me(MMe)88M8M (88ee, 8.8888eeee) eee eeeee. Meeee eee eeeeeee eee eeeeee, e eeee eeeeeeee eeee eee eeeeeeee eee 88e eee eeee eeeeeee ee eeee ee ee. Mee eeee eee eeee eeeeee eeee 88% ee MeMMM8 (88eM), eeeee eeeeeeee ee eeeeeeeeeeeee ee e eeeee. Mee eeeeeee eee eeeeee ee eee eee eee eeeee eeee eeeeee eee eeeeeeeee ee eeeeeee eeeeeeeeee eee eeeee ee e eeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eeeee eeeeeeee; eeeee: 8.88e (88%).

(Meeeeeeeeeeeeee)eeeeeee (88, M8=Me; M8=M; M8=Me; Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee Meeeeeeeee:[‌888‌]

Me e eeee ee MeMMM (888ee, 8.888eeee) eee MM(MMe)8 (8.8eM), 8.888eeee) ee eeeee MeMM (8.8eM) eee eeeee eeeeeeeeee (8.8ee, 8.88eeee) eee eee eeeeeeeee eeee eee eeeeeee ee ee eeeee M8. Mee eeeeeeee eee eeeeeeeee ee MMM (MeMMe/eeeeee 8:8). Meeee 8eee, eee eeeeeeee eee eeeeeeee ee eeeeee eee. ee M8MM8 (88eM) eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeee eeeee eee eeeeee eeee M8M, eee. MeMe eeee, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeeeee eeeeee; eeeee: 888ee (88%).

(8,8-Meeeeeeeeeeeee)eeeeeee (88, M8 = Me; M8 = Me; M8 = Me; Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeeeeeeeeee (888 e, 8.88 eee), MeMM (888 e, 8.88 eee), 8,8-eeeeeeeeeeeeeeee (888 e, 8.8 eee), eeeeee (888 eM), eee MeMM (8.8 e) eee eeeeeeeee eeeeeee e 888 × 8.8 ee eeeeee eeeeee eeee 88 ee eeeee eeeeeee eeee eee eeeeee eeeee eeeee eeeeeeee ee eeee eee eeee eeeeeeeeeee eeeeeeee eeeee 88°M. Meeee eeee 888888 eM ee eeeeeeeeee eee eeeeeeee, ee eeeee eeeeee ee eeeeee eee eeeee ee eee eeeeeee eeee eeeee 888 eM ee eeeeeeeeee eee eeee eeeeeeeee. Mee eeeee-eeee eeeeeeeeeee eeee eeeeee eeee ee 88°M, ee eeeee eeee eee eeeee eeeeeeeeee eee 888 eM. Mee eeeeeeee eeeeeee eee eeee eeeeeeee ee eeeeeee eeeeee MeMMe (8.8 e) ee MeMM (88 eM). Meeeeeeeeeee eee eeeeeee eee eee eeeeeeee eee eeeeeee ee eeeeeeeee ee eeee eee eeeeeeeeeee ee eee eeeee eeeee 888888°M. Meeee e eeeeeee eeee eeeeeeee eeee 8,8-eeeeeeeeeeeeeeee, e eeeeeee ee 888 eM eeeeeeee. Meeee eee eeeeeeeeeeeee eeeeeee e 8.8-ee eeeeee eeeeee eeee Meee eeeeeee, eeee eeeeeee eeee eee eeeeeee; eeeee: 888 e (88%); ee 88°M/8 Meee.

8,8-Meeeeeeeeeeeeeeeeeee [88, M8,M8=(MM8)8; M8=Me; Meeee 8, Meeee 8]; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeee eee ee e eeeeee eeeeeeee ee eee eeee, eeee, eee eeeeee eeeeeeeee.

M eeeeeee ee eeeeeeeeeeeee (88e, 8.8eee), eeeeeeee eeeeeee (88e, 8.88eee), eee MeMM (88eM), eee 88.8% MMe ee MeMM (8eM) eee eeeeeeee. Meeee e eee eee, e eeeeeeee eeeeeeeee ee MM8 eeeeeee, eeeee eeeeee eeeee eeeee 8e. Meeeeee eee eeeeeeeee eee 8e, eeeeee eee eee-eeeee eeeeeee eee eeee eeeeeeee ee eeeeeeee ee e eee eeeee ee MeMMe eeee. Mee eeeeeee eee eeeeee eeee 88% ee MMM eeee (888eM) ee eeeeeee eeeeeeeee eeeeeeee eeeeeee. Meeee eeeeeeee ee eee eeeeeee eeee M8M, ee eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeee (M8MM8) eee eeeeeeeee; eeeee: 88e (88%); ee 8888°M/88.8Meee.

(Meeeeeeeeeeeeee)eeeeeee (88, M8=Me; M8=M; M8=Me; Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

MeMMM (8.88e, 88eeee) eee eeeee eeee eeeee MeMM (88eM) ee e eeeee-eeeeeeee eeeee. Mee eeeeeeeeeeeeee M8MeM88M88eM8M ee M8MMe88M88eM8M (8.8e) eee eeeee ee eee eeeee eee eee eeeeeee eee eeeeeee eeee e eeeeeeee eeeeeee ee ee eee 888eee. Meee, MeMM8 (8.8e) eee eeeee ee eeee eee M8M eeeeeeee ee eee eeeeeeee eee ee eeeee eee eeeeeeee ee eeeeeeeeee. MeMM eee eeeeeeeeee ee e eeeeee eeeeeeeeee eee eee eeeeeee eee eeeeeee eeee eeeeee Me8M ee MM8Me8. Mee Me8M eeeee eee eeeeee eeee M8M eee eeee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeeeee ee eeee eee eeeeee; eeeee: 8.88e (eeeee).

References