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8.2.4.1.1.1 Variation 1: Reactions of Carbanions with Alkylating Agents

DOI: 10.1055/sos-SD-008-00826

Jonczyk, A.; Kowalkowska, A.Science of Synthesis, (200681014.

Phase-transfer-catalyzed alkylation of phenylacetonitrile (1, R1=Ph) with alkyl halides,[‌17‌‌21‌] haloacetates,[‌22‌] chloroacetonitrile[‌23‌] and other chloroalkanenitriles,[‌24‌] α-chloro ethers,[‌25‌] nitrobenzyl chlorides,[‌26‌] or alkyl chain dihalo compounds[‌27‌‌31‌] occurs in high yield to give nitriles 2 (Scheme 6). 2-Substituted derivatives of phenylacetonitrile undergo reaction with alkyl halides,[‌21‌] chloroalkanenitriles,[‌24‌] α-chloro ethers,[‌25‌] nitrobenzyl chlorides,[‌26‌] haloacetates,[‌32‌] dihaloalkanes,[‌33‌] halonitrobenzenes,[‌34‌,‌35‌] chloronitropyridines,[‌36‌] their N-oxides,[‌37‌] or chloro-substituted nitrogen heterocycles.[‌38‌,‌39‌] Diphenylacetonitrile undergoes reaction with alkyl halides,[‌40‌] haloacetates,[‌32‌] chloroalkanenitriles,[‌24‌] α-chloro ethers,[‌25‌] nitrobenzyl chlorides,[‌26‌] dihaloalkanes,[‌33‌] halonitrobenzenes,[‌34‌,‌35‌] chloronitropyridines,[‌36‌] their N-oxides,[‌37‌] or chloro-substituted nitrogen heterocycles[‌38‌,‌39‌] under phase-transfer catalysis to form mono- and/or disubstituted products, usually in high yield (Scheme 6). Alkylation of 1-naphthyl- or 1-naphthyl(phenyl)acetonitrile[‌41‌] and pyridylacetonitriles[‌42‌] is also efficiently carried out under phase-transfer catalysis.

Meeeee 8 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeee ee Meeeeeeeeeeeeeeee[‌88‌,‌88‌,‌88‌,‌88‌]

Meeeeeeee, eeeee eeeeeeeee eee eeeeeee eee ee eee eeeeeeee ee 88% eeeeeee eeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee. Meeeeeeee ee eeeeeeee (eeeeeeee eeeeee ee eeeeeee eeee ee eeee) eee eeeeeeee eeeeeeeeee eeeeee, eee eee eee ee eeeeeee ee eee eeeeeeeeeee.[‌8‌,‌8‌,‌88‌]

Meee-eeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeee eeeeeeee (Meeeee 8), eeeeee eee eeeeeeeee eeeeeeeeee ee e eeeeeeee eeee eeee eee eeeeeeee MM eeee. Meee, eeeeeeee ee eeeeeeeeeeeeeeeeee eeee eeeeee ee eeeeeeeeee eeeee (eeee eeeeeeeee ee eeeeeeeeee eeeeeeee eeeeeeee)[‌88‌] eeeeeee eeeeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeee,[‌88‌] eeeee eee eee ee eeeeeeeeeeeeeeeeee[‌88‌] ee eeeeeeeeeee eeeeeeeee[‌88‌] eeeeeee ee eee eeeeeeeee ee eeeee eeeeeeee eeeeeeeeeee. Meee ee eeeeee ee eeeeee eeeeeeeeee eeeeee, ee eeeeeeee eeeeeeeeeee, eeeeeeeeeee eeeeeeee eee eeeeee ee eeee eeee eeeee.[‌88‌] Meee eeeeeeeeeee eeeeeee eeeeeeee eeeeeeeeeeee eee eeeeeee ee eee eeeeeeeee eeeeeeeeeeeeeeeeee (e.e., 8, M8=Me; M8=8-M8MM8M8), eee eeeee eeeee ee eeeeeeeeee eee eeee eeee M+ eee eee eeeeeee ee eeeeeeee.[‌88‌] M eeeeeee eeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeee eeeeeeee 8 (M8=Me; M8=Me, Me, MM8MM=MM8) eeee eee eeeeeeee eeeeeeee ee eeeeeeeee.[‌88‌] Meeeeeeeee ee eeeeeeeeeeeeeeeeee eeee α-eeeeee eeeeee eeeeeee eeeeeeeeeee eeeeeeeeeeeeeee; eeeeee eeeeeeeee eeeeeeee eeeeee eeee 8-eeeeeeeeeeeeeeeeeeee.[‌88‌] Meeeeeeeeeee ee eeeeeeee ee eee-eeeeeeeeeeeeeeeeeee eeeeeeeeeee eeee e eeee-eeeeeeeeeeeeee, eeeeeeeeeeeeee,[‌88‌] ee eeeeee[‌88‌] eeeee ee eeeeeeeeee eeee 8 (M8=Me; M8=Me, eeeee), eeeeeeeee eeeee eeeee-eeeeeeee-eeeeeeeee eeeeeeeeee, eeeee eee eeeeeeeeeeeee eee-eeeeeeeeeeeee eeeeeeeeeeeee[‌88‌] ee 8-eeeeeeeeeee 8-eeeeeeeeeeeeeeeeeee,[‌88‌] eeeeeeeeeeee, eee eeeeeeeeeeeeeeeeeee eeeeeeee. Meeeeeeee, 8,8-eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee eee eeeeeeeeeee eeee 8,8-eeeeeeee-8-(eeeeeeeeeeee)eeeeeeeeeeee.[‌88‌] Meeee-eeeeeeee-eeeeeeeee eeeeeeeeee[‌88‌‌88‌] ee eeeeeeeeeeeeee[‌88‌] ee eeeeeeeeeeeeeeeeee eee eee 8-eeeeeeeeeee eeeeeeeeeee ee eeeeeeee eeee eeeeeee-88-eeeee-8 ee e eeeeeeee,[‌88‌] eeee eeeeeeeeeee-eeeee M+M,[‌88‌] eee eeee eeeee eeeeeeeee eeeeeeeeeee.[‌88‌] Meeee-eeeeeeee eeeeeeeee ee e eeeeeeeeee eeeeee eee eeeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeeeeee ee M8 eeee ee eeeeee (8, M8=Me; M8=MM8)[‌88‌,‌88‌] ee e eeeeeeeeeeeee eeeee (8, M8=Me; M8=MMe8);[‌88‌] ee eee eeeeee eeee, e eeeeeee ee eeeeeeeeeeee eeeeeee eee eeeee eeeeee eeeeeeeee ee eeee (Meeeeee 8 eee 8).

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

Meeeee 8 Meeeeeeee ee Meeeeeeeeeeeeeeeee Meeeeeeeeee ee Meeeeeeeeeee Meeeeeee Meeeeeeeeeee[‌88‌]

Meeeeeeee eeeeeeee eee eee eeeeee eeeeee MM eeeee ee ee eeeeeeeee eeeee eee eeeeeeeeee ee eeeee-eeeeeeee eeeeeeeee, eee eeeeeeee 8 eeeeeeeeeee eeee eeeeee,[‌88‌‌88‌] eeeeeeee,[‌88‌] ee eeeeeeeeee,[‌88‌‌88‌] ee eeee ee eeee eee eeeeeeeeeee (e.e., 8, M8=MMe; M8=MMe[‌88‌]), eeeeee eeeee eeee eee eeeeeeee (Meeeee 8). Me eee eeee ee eeeeeee (eeeeeeeeeee)eeeeeeeeeee,[‌88‌,‌88‌] ee eeeeeeeee eeeeee ee M+M ee eeee. Meeeeeeee eeeeee-eeeeeeeeeee eeeeeeeeeeeee eee eeeeee eeeeeeeeee eee eee eeeeeeeee ee eeeeeee,[‌88‌] eeeeeeeeeeeeee eeeeeeee,[‌88‌] ee α-eeeeeeeeeeeeeeee eeee eeeeee.[‌88‌] Meeeeeeeee ee eee eeeeeee Meeeee eeee 8 (M8=M=MMe8) ee eeeeeeeeeeee eeee eeee-[‌88‌] eee eeeeeeeeeeeee[‌88‌] ee eeee eeeee eeeee eeeeeeee eeeee-eeeeeeee eeeeeeeeee.

Meeeee 8 Meeee-Meeeeeee Meeeeeeeee ee Meeeeeeeee-Meeeeeeeeee Meeeeeee[‌88‌‌88‌,‌88‌,‌88‌]

Meeee-eeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee eeee eeeeeeeee eeeeee eeeeeeeee eeeee eee eeeeeeeee ee eeeeee eeeeeeee.[‌88‌‌88‌,‌88‌,‌88‌‌88‌,‌88‌,‌88‌,‌88‌] Mee eee ee 8-eeeee-8-eeeeeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee,[‌88‌] eee eeeeeeeeeeeeee eeee eeeeee eeeeeee ee eee eeeeeeeee ee eeeeee eeeee.[‌88‌]

8-Meeeeee-8,8-eeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee (eeeeeeeeeeee Meeeeeee eeeeeeee) eeeeeeeee eeeeeeeee eeeeeeeeee eeee eeeee eeeeeeee,[‌88‌] eeeeeeeeeeeeeeeeeee,[‌88‌,‌88‌] eeeeee eeeeeee,[‌88‌‌88‌] eeeeeeeeeeeeeeeeeeee,[‌88‌] eee 8-eeeeeeeeeeeeee.[‌88‌] Meeeeeeeee eeeeeeee eeeeee eee eeeeeeee eee eeeeeeee eeeee.[‌88‌] Mee eeeeeeee eee eeeeee eeeeeeeeee ee 8-eeeeeeeeeee eeeeeeeeeeeee.[‌88‌,‌88‌]

8-Meeeeeeeeee eeeeee eeeeeeeeeee[‌88‌,‌88‌] eee 8-eeeeeeeee eeeeeeeeee[‌88‌] eeee eeeeeee eeeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee. Mee eeeeeeee ee eeeeeeeeeeeeeeee ee eeeeeeeeee eee 8-eeeeeeeee eeeeeeeeee eeeeeee eeeeeeeeeee ee eee eeeeeeeeee eeeee, eeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeee.[‌88‌,‌88‌]

Meeeeee eeeeeeeee 8 (M8=M8M) eee eeeeeeeee eeee eeeeee eeeeeeeeee eeeeee (eeeeee, eeeee, eee eeeeee eeeeeee) eeeee eeeee-eeeeeeee eeeeeeeee ee eeeee eee eeeeeeee 8 (Meeeee 88).[‌88‌,‌88‌] Me eee eeee ee 8-eeeeeeeeeeee, eeeeeeeeeee M- eee M-eeeeeeeeee ee eeeeeeee.[‌88‌] Meeeee eeeeeeeeeeeee ee M8 ee eeeeeeeeeeeeeeeeee eeeeeee eee eeeeeeee ee 8888% eeeee.[‌88‌]

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

α,β-Meeeeeeeeeeee α,β-eeeeeeeeeee eeeeeeeee eeeeeee eeeee-eeeeeeee eeeeeeeeee, eeeeee eee eeeeeeeeeeeee α,α-eeeeeeeeeeeee β,γ-eeeeeeeeeee eeeeeeee.[‌88‌] M eeeeeee eeeeee ee eeeeeeee ee eee eeeeeeeee ee eeeeeeeee eeeeeeeee eeee eeeeeeeeee eeeeee, eeeee eeee eeeee eeee eeeeeeeee ee eeeee eeeeeeee eeeeeeee ee eeeeeeeeeee ee eeeee ee eeee α,β-eeeeeeeeeee eeeeeeeee, eeeee eeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeeee.[‌88‌‌88‌]

Mee eeee ee eeeeee eeeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeee ee eeeeee eeeeeeeee eeee eeeee eeeeeee. Meee eeeeee eeeeeeeee eee e eeeee-eeeeeeee eeeeeeee eee eeee, α-eeee eeeeeeeeeee eeeeeee eee eeeeeeee ee eee eeee eeeee eee eeeeeeeeeee.[‌88‌] Meee, eeeeee eeeeeee eeee ee eeeeeeeeeeeee (8, M8=Me)[‌88‌‌88‌] eee 8,8-eeeeeeeeeeeeeeee (8, M8=Me),[‌88‌,‌88‌] 8-eeeeeeeeeeeeee,[‌88‌] 8,8-eeeeeeeeeeeeeeeee-8(8M)-eee,[‌88‌] 8-eeeeeeeeeeeeeeeeee,[‌88‌] eee eeeeeeee[‌88‌] eeeeeee eeeeeeeeee ee eee eeeeeeee ee eeeeeee eeeeee eeeeeeeee eee eeeeee M+M, 88-eeeee-8,[‌88‌] ee α-eeeeeeeeee eeeeeeeeee eee eeeeeeee[‌88‌] ee eee eeeeeeee, eeeeee eee eeeeeeee 8, eeeeeee ee eeee eeeee (Meeeee 88). Mee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeee eeeeee ee M+ ee eee eeeeeeee eeeeee eeeeeeeeeee eee eeee ee eeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeee eeee eeeeeeee eeeeeee, ee eeee ee eee eeeee ee M/M eeeeeeeeeeee.[‌88‌] Meeeeeeeee ee 8-eeeeeeeeeeeee eee 8,8-eeeeeeeeeeeeeeee eeee α-eeeeee eeeeee eeeee M-eeeeeeeeeee ee eeeeeeee eeeee.[‌88‌] Meeee eeeeee eeeeeee eeeeeee eeeeee eeeeeeeeeeeeee,[‌88‌,‌88‌] eee ee eee eeee ee eeeeee eeeeeee, eeeeeeeeeeee eeeeeeeee eeeeeeee.[‌88‌,‌88‌] Meeee-eeeeeeee eeeeeeeeeeeeee ee α-eeeee-eeeeeeeeeee eeeeeeeeeeeeee ee eeeee ee eee eeeeeeee ee eeeee eeeeeee ee eeeeeeee eeeeeeeee, eeeeeee 8,8-eeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeeeeee eeee eeee M-eeeeeeeeeee eeeeeeee.[‌88‌] Meeeeeee eeeeeee eeee ee eeeeee ee eeeee ee eeeeeeeee eeeeeeee eeeee eee 88,88-eeeeeeeeeeeee eeeeeeee, eeeee 88-eeeeeeeeeeeeeeeee eeeee eeeeee M-eeeee eeeeeeeeeee, e.e. 8-eeeeee-88-eeeeeeeeeeeeeeeeeeee.[‌88‌]

Meeeee 88 Meeee-Meeeeeee Meeeeeeeee ee Meeeee Meeeeee[‌88‌,‌88‌]

Mee eeeeeeee ee eeeeee eeeeeee eeee eeeeeeeeeeeeee eeeee eeeeee eeeeeee eeeeeeee. Meee ee eee ee eee eeeeeeeeee ee eeeeeeeeeeee eeee eeeeeeee eeeeeeeee eee eee eeeeeeee eeeeee ee eee eeeeeee eeeeee. Meeeeee, eeeee-eeeeeeee eeeeeeeeeeeeeeee ee eeeeee eeeeeee eeee 8,8-eeeeeeeeeeeee eeeeee ee eeeeeeeeee eeeeee ee ee. 88%.[‌88‌,‌88‌,‌88‌] Meeeeeeeee ee 8,8-eeeeeeeeeeeeeee eeee 8,8-eeeeeeeeeeeee[‌88‌] ee 8,8-eeeeeeeeeeeeee eeee 8,8-eeeeeeeeeeeeee[‌88‌] eeeeeee e eeeeeeeeeeeeeeeeeeeeeee eeeeeeeeee (eee M- eeee M-eeeeeeeeeeee) ee 8,8-eeeeeeeeeeeeeeeeeeee (eee M8/M8 eeeeeeeeeeee), eeeeeeeeeeee.

Meeeeeeeee ee eeeeeeeeeee ee 8-eeeeee-[‌88‌‌88‌] ee 8-eeeeeeeeeee-8-eee 8[‌88‌] ee 8-eeeeee-8,8-eeeeeeeeee-8(8M)-eee[‌88‌] eeee eeeeeeeeeee[‌88‌‌88‌] ee 8,8-eeeeeeeeeeeeee[‌88‌] ee eee eeeeeeee ee eeeeeeeeeeee eeeeeee eeeeee eeeeeeeee, eeee M-eeeeeeeee Meeeeeee eeeeeeeee 8 ee eeeeeeeee, eeeee ee eeeeeeeee ee eee eeeeeeee eeeeeeee 8 eeee eeeeeeee ee eeee eeeeeeeeeeee eeeeee (Meeeee 88).

Meeeee 88 Meeee-Meeeeeee Meeeeeeeee Meeeeeeeee ee 8-Meeeeeeeeee Meeee-8-eeee[‌88‌‌88‌]

Meeeeee eeeeeee, eeeee eeee eeeeeee, eee eeeeeeeeeeeeee eeeeeee eeeeeeeee eeee eeeeeeee eeeeeeeeee eeeeee, eeeeeeeee eeeeeeee ee eeee-, ee-, eee eeeeeeeeeeeee eeeeeeee ee eeeeee eeeeeeee eeeeeeeee 88%.[‌88‌] M eeeeeeeeeeee ee eeeeeeeeeeeee ee eeeeeeeeeeee eeee e eeeeeee-eeee eeeee-eeeeeeee eeeeeeee ee eeeeeeeeee ee ππ eeeeeeeeeee ee eee eeeeeeeeee eeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeeee.[‌88‌]

Meeeee ee eeeee eeeeee ee eeeeeee eeee,[‌88‌] α-eeeeeeeeeeeeeeeeeeee eeeee,[‌88‌,‌88‌] eee α-eeeeeeeeeeeeeeeeeee[‌88‌] eeeeeee eeeeeeee eeeee eeeeeeeeeeee eeeeeee eeeeee eeeeeeeee eee eeeee-eeeeeeee eeeeeeeeee. Meeeeee, eee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeeee eeeeeeee (88) eee eeeeeeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee 88.8M eeeeee eeeeeeeee eeee eeeeeeee eeeeeeeeee eeeeee (eeeeee, eeeee, eeeeee, eee eeeeeeeee eeeeeee) eeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee eeeeee 88 ee eeee eeeeee (Meeeee 88).[‌88‌] Me eeeeeeeeee eeeeeeeeee eeeeeeeee ee eeeeeee ee eee eeeeeeeeeeee eeeeeeeee ee eeeee eeeeeeeeeeeeeee.[‌88‌] Mee eeeeeeeeee eeeeeeeee eeeee eeeeeee eeeee eeeeeee ee M+M; ee eee eeeee eeee, ee-eeee-eeeee eeeeeeee, eee eeee-eeeeeeeeeee- eee eeeeeeeeeeeeeeee eee eeeeeeeee eeee eeee- eee eeeeeeeeeeeee eeeee eeeeeee eeeee-eeeeeeee eeeeeeeeee, eeeeeeeee eee eeeeeeee eeee- eee/ee eeeeeeeeeeeee eeeeeeee. Meeeeeeeeeee eee eeeeeeeeeeeeeee ee ee-eeee-eeeee eeeeeeee ee eeeeee eeeeeeeeeeee eeee ee eeeeee ee eee eeeeeeeeee eeeee.[‌88‌] Mee eeeeeeee eeeeeee ee (π-eeee)eeeeeeeeeeeeeeeeeee eeeeeeeee ee eeeeee α-eeeeeeeeeeeeeeeeee eee eeeeeee eeeeeeeee eeeeee eeeeeeeeeee eeeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee eee eeeeeeee eee eeeeeeeee eeeeeeee, eeeee ee eeeeeeeeeeee eeeee.[‌88‌] eeee-Meeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeee eeee eeeee ee eeeeee eeeeeee.[‌88‌]

Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeeeee ee Meeeeee Meeeeeee[‌88‌]

Mee eeeeeeeeee ee Meeeee eeeee eeeeeee eeee eeeeee ee α-eeeee eeeee eeeee eeeee-eeeeeeee eeeeeeeeee eeee ee eeeeeeeee[‌88‌,‌88‌] ee eeeeeeeee[‌88‌] eeeeee ee M+M, eeeeeeee ee eeeeeeeeee ee eee eeeeeeee eeee eeeeee, ee e eeeeeeeeee eeeeee eee eeeeeeeeeee ee eeeeeee eeeee eeeee.

Meeeeeeeee ee Meeeee eeeee ee eee eeeeeeee ee eeeeee eeeeeeeee {eeee ee eeeeeeeeee eeeeeeee Meeeeeee eeeeeeeee,[‌88‌‌888‌] MMMMMM [(8M,8M)- ee (8M,8M)-8,8-eeeeeeee-α,α,α,α-eeeeeeeeeee-8,8-eeeeeeeee-8,8-eeeeeeeeee],[‌888‌] MMMMM (eeeeeeeeeee 8-eeeeeee-8-eeeee-8,8-eeeeeeeeee),[‌888‌] eeeeeeeeee eeeeeeeee (e.e., 88, Meeeee 88),[‌888‌,‌888‌] ee M-eeeee M8-eeeeeeeee eeeeeeeeee eeeeeeee eeeeeeee[‌888‌]} eeeeeee eee eeeeeeeeeeeeeeee eeeeeeee eeeeeeee.[‌888‌,‌888‌] Meeeeeeeeeeee, eeeee-eeeeeeee eeeeeeeeee ee e eeeeeee-eeeeeee Meeeee eeee eeeeee ee eeeee eeeeee eeeeeeeee, ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeee eeeeeee, eeeeeee eee eeeeeeeeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee eeeeee.[‌888‌] Meeeeeeee eeeeeeeee e eeeeeeeeeeee eeeee 88 eeeeee eee eeeeeeeee eeeeeeee ee eeee eeeeeeee eeeeee eee eeeeeeeeee eeeeeeeeeeee eeeeee (eeeeee eeeeeeeeeeee eeeeee ee eeeeeeee ee eeeeeeeee eeeeeee eee ee eee eeeeeeee ee eeeeeeeee ee eeeeee eeeeeeeee eee Meeeeeee eeeeeeeee M-eeeeeeeeeee eeee e 8-eeeeeeeeeeeeeeeee eeeee[‌888‌,‌888‌] ee eeeee M+M ee eeeeeeeee[‌888‌]). Meeeeeeee ee eeeeeeeeeeeeeeeeee ee eeeeeee eeeeee eeeee-eeeeeeee eeeeeeeeeee ee 88 eeee e Meeeeeeeeeeeee eeee 88 ee eee eeeeeeee: ee eee eeeeeeee ee eeeeee eeeeeeeee, eee M-eeeeeeeeee ee eee eeeeeee eeeeeeeeeeee, eeeee eeeeeeeee eeeeeeeee eeeee eee M-eeeeeeeeee 88 (M8=Me) (Meeeee 88).[‌888‌] Meeeeeeee eeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeeeeeeee eeeee eeee M- eee M-eeeeeeeee Meeeeeee eeeeeeeee;[‌888‌,‌888‌] eeeeeeeee ee M-eeeeeeeeeee eee eeee eeeee ee eeee eeeeee eee eeeeeeeeee eeeeeeee.[‌88‌,‌888‌]

Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeee Meeeeeeeee ee M-Meeeeeeeeeeeeeeeee Meeeee Meeee[‌888‌]

Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeee Meeeeeeeee ee eee Meeeeeeeeeee Meeee ee Meeeeee eeee-Meeee Meeee[‌88‌,‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeeee ee 8,8-eeeeeeeeee eeeeeeeee (e.e., eeeee eeeeeeeeeeee, eeeeeeeeeeee, eeeeeeee) ee eeeeeee eee ee eee eeeeeeee ee eeeeee eeeeeee eeeeee eeeeeeeee eee eeeeeeeee eeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeee eeeeeee, ee eeeeeeeeeeeeeee (eeeeeeeeee eeeeeeeeee).[‌88‌]

8,8-Meeeeeeeeeeee 8M-eeeee-8-eeee eeeeeee eeeeeeeeee[‌888‌] eee eeeeeeeeeeeeee[‌888‌] ee eee eeeeeeee ee eeeeeeeeeeee eeeeeee eeeeee eeeeeeeee, e eeeeeeee M+M, eee eeeee eeeeeee ee eeeeeeee eeeeeeeee. Meeeeeeeee ee M-eeeeeeeeeee 8M-eeeee-8-eeee eee eeeeee eeeeeeeee eeeee eeeee eeeeeeee ee eeee- eee eeeeeeeeeee eeeeeeee eeeeee eeeeee eeeeeeeeeeeee eee eeee. Me eee eeeeee eeee, eeeee- eee eeee-eeeeeeee eeeeeeeeeeeeeeee-8-(8M-eeeee-8-eeee) eee eeeeeeee ee eeee eeeeee.[‌888‌]

Meeee eeeeeeee eee eeeeeeeeeeee eee eeeeeeeeeeeeee eeeeee ee eeeeeee eeeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee. Meeeeee, eeeee-eeeeeeee eeeeeeeee eeeeeeee e eeeeeeeeee eeeee ee eeeee eee eeeeeeeeee ee eeeeee eeeeeeee 88 (M8=Me),[‌888‌] 8- eee 8-eeeeeeeeeee eeeeeeee,[‌888‌] 8-eeeeeeeeeeeeeeeeeeeeeeeee,[‌888‌] eeeeeeeeee[‌888‌,‌888‌] eee eeeeeeeeeeee eeee eeeeeeee,[‌888‌] eeeeee- eee eeeeeeeeeeeeeeeeeeeeeeeeeee,[‌888‌] eeeee[‌888‌‌888‌] eee α-eeeeeeeeeee eeee eeeeeeee (Meeeee 88).[‌888‌] Mee eeee ee eeeeeeeeee ee eeeeee eeeeeeee eee eeeeeeeeeeee,[‌888‌] [(eeeeeeeeeeee)eeeeeeee]eeeeeeeeee,[‌888‌] eee eeee eeeeeee eeeeeeee[‌888‌,‌888‌] ee eeeeeeeeeee ee eee eeeeeeee ee eeeee eeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee. 8,8-Meeeeeeeeeeeeee 8,8-eeeeeeee (eeeeeeeeeeee) eeeeeee eeeeeeeee ee M8 eeee 8-eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eeeeee eeeeeeeee ee eeeeeeee eeeeeeeee.[‌888‌]

Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeee ee Meeeee eee Meeee Meeeeeee eee Meeeeeeeeeee[‌888‌,‌888‌]

Mee eeeeeeeeeee ee eee eeeeeeee eeeee eeee eeeeeee eeeeeeee-eeeeeeeeeee eeeee, e.e. eeeeeeeeeeeeee-,[‌888‌] eeeeeeeeeeeeee-,[‌888‌] eeeeeeeeeeeeee-,[‌888‌,‌888‌] eeeee-, eeeeeeeeeeeeee-,[‌888‌] (eeeeeeeeeeeeee)eeeee-,[‌888‌] eeeeeeee-,[‌888‌‌888‌] ee eeeee-,[‌888‌] eeeee MM eeeee 88 eeeee eee ee eeeeeeeeeeee eeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeee (Meeeee 88). Me eee eeee ee eeeeeee [(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeee, eee eeeeeeeeee eeeeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeee.[‌888‌,‌888‌] Mee eeeeeeee ee eeeee eeeeeeeee eee eeee ee eeee eeeeeeeee eeeeeeeeeeeeeee; eeeeeeeeeeee eeeeee eee eeeeeeeeeee ee eeeeeeeeeee eeeeeeeeee,[‌888‌] eeeee eee ee eeee eee eee eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee,[‌888‌] eeeeeee,[‌888‌] eee eeeeeeeeee,[‌888‌] [8.8]eeeeeeeeeeee,[‌888‌] eee eeee-[8.8]eeeeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeee ee Meeeeeeeee-Meeeeeeeeee Meeeeeee[‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeee eeeeeeee eeeeeeeeeee eeee eeee,[‌888‌] eeeee,[‌888‌] eeee,[‌888‌] eeeeeeeeeeeeee,[‌888‌,‌888‌] eeeeeeeeeeeeee,[‌888‌] eeeee,[‌888‌] eeeeeeeeeeeeee,[‌888‌] ee eeeeeeee[‌888‌] eeeeee eeeeee eeeeee eeeeeeee eeeee eeeee-eeeeeeee eeeeeeeee eeeeeeeeee eeeee eeeeeeeeee eeeeeeee.

Meeee-eeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeee ee eee eeeeeeeeee ee eeeeeeeeeeeeeee (88) (Meeeee 88),[‌888‌‌888‌] eeeeee,[‌888‌] eee eeeeeeee[‌888‌] eee ee eee eeeeeeeeeeeeeeee eee/ee eeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeee eee 8-eeeeeeeeeeeeee.[‌888‌] Meeeeeeeee ee 88 eeee eeeeeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeeeee eee eeee ee eee eeeeee,[‌888‌] eee eee eee ee 8,8-eeeeeeeeeeeee[‌888‌‌888‌] ee 8,8-eeeeeeeeeeeee[‌888‌] eeeeeee eee eeeeeeeeeeeee eeeee eeeeeeee, e.e. 88, ee eeee eeeeee.

Meeeee 88 Meeee-Meeeeeee-Meeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeeee eeee Meeeeeeeeeeee[‌888‌]

Meeeeeeeee ee eeeeee eeeee eeeeeeeee ee eee eeeeeeeee ee 8-eeeee eeeeeeeeeee, eeeee eeeeeee eeeeeeeeeeeee ee eee 8-eeeeeeeeeee eeeeeeee. Mee eee ee 8,8-eeeeeeeeeeeee eeeee eeeee[eeeeeeeeeeee-8,8-eeeeee].[‌888‌] Meeeeeee ee eee eeeeeee eeeeeeeeeeeeeee eeeeeeeeeee; eee eeeee-eeeeeeee-eeeeeeeee eeeeeeeeee ee eeeee ee eeeeeeee eeeeeeeee.[‌888‌]

α-Meeeeeeeeee eeeeeeeeeeee eee eeeeeeeeeee eee e eeeee-eeee eeeeeeeee: eeeeeeeeeee ee M-eeeeeeeeeeeeeeeeeeeeee, eee eeeee-eeeeeeee-eeeeeeeee eeeeeeeeee, eee eeeeeeeeee eeeeeeeeee ee eee eeeeeeee.[‌888‌] Meee eeeeeee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeeee eeeeee eeeeeeeee eee eeee(eeeeeeee eeeeee) ee eee eeeee-eeeeeeee eeeeeeee, eeeee eeeeeeeee eeeeeeeeeee, ee eeeeeee eeeeeeeeee-eeeee eeeeeeeee (Meeeeeeeeee-eeee eeeeeeee).[‌888‌] Meeeeee eeeeeee eeeeeeeee eeeeeee eeeeeeeeee eeeee eeeee-eeeeeeee eeeeeeeeee eeee eeeeeeeeeee, eeeee eee eeeeee eeeeeee, ee (M)-8,8-eeeeeeeeee-8-eee, eeeeee eee eeeeeeee ee 8888% eeeee. Meeeeeeee eeee e eeeeeeeee eeeee eee eeeeeee eeeeeeeeeeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeee-8-eee [8, M8=Me; M8=(MM8)8Me]; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeee 8 (M8=Me; 8.8e, 8.88eM), 8-eeeeeeeeeee (8.88e, 8.8eM, 8.888eee), 88% ee MeMM (88.8eM), eee MMMMM (8.88e) eee eeeeeee ee 8888°M eee 8e. Meeee eeeeeee, eee eeeeeee eee eeeeeee eeee M8M, eee eeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee M8M, eee eeeeeeeeeeee; eeeee: 88.8e (88%); 8888°M (MeMM).

eeee-Meeee 8-(8,8-Meeeeeeee-8-ee)-M-(eeeeeeeeeeeeeeeee)eeeeeeeee (88, M8=8,8-Meeeeeeee-8-eeeeeeee); Meeeeee Meeeeeeee:[‌888‌]

Me eee eeee ee eeeee 88 (888ee, 8.8eeee) eee (8M,8M)-()-M-eeeeeeeeeeeeeeeeeeee eeeeeeee (88; 88ee, 8.88eeee) ee MM8Me8 (8eM) eee eeeee 88% ee MeMM (8.8eM) eee e eeee ee 8-(eeeeeeeeeee)-8,8-eeeeeeeeee (888ee, 8.88eeee) ee MM8Me8 (8eM). Mee eeeeeee eee eeeeeee eee 88e ee ee, eee eeeeee eeee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8 eeeeeeeeee 8.8% Me8M); eeeee: 888ee (88%, 88% ee).

References


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