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3.1.2.2.1.1.1 Formation of Indoles

DOI: 10.1055/sos-SD-209-00235

Stewart, S. G.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20133442.

The intramolecular Heck cross-coupling reaction is now commonplace for the construction of the indole ring system and can be applied to a range of substrates. Initially, the group of Mori described an intramolecular Heck reaction involving various aryl halides containing an activated acrylate side chain.[‌2‌] This process, employing palladium(II) acetate and triphenylphosphine, affords methyl (1-acetyl-1H-indol-3-yl)acetate in good to moderate yields. Following the 5-exo-cyclization bond-forming rationale, other reactions from N-allylated anilines bearing an ortho-halide have been among the most common. The Hegedus group subsequently reported the Heck reaction of reactive N-allyl-2-haloaniline systems with palladium(II) acetate and triethylamine in acetonitrile; it was found that the addition of tri-2-tolylphosphine serves to ensure that aryl bromides are viable substrates.[‌3‌] The preparation of indoles, including N-methyl and ether variants, was later described by the Larock group; in the simplest example, 3-methyl-1H-indole (5) was prepared from the iodoaryl precursor 4 in 97% yield, through treatment with palladium(II) acetate, sodium carbonate, and a phase-transfer catalyst (Scheme 2).[‌4‌] In similar methods, using either aryl bromides (e.g., 7) or chlorides, more elaborate catalytic systems containing N-heterocyclic carbenes (e.g., 6; counterion X not known) can be used (Scheme 3). Generally, as for other Heck reactions, aryl chloride systems result in a poorer turnover.[‌5‌] Additionally, this approach has been conducted on a solid support.[‌6‌]

Meeeee 8 Meeeeeeeeeeeee Meee Meeeeeee ee ee Meee Meeeee Me Meee 8-Meeeee-8M-eeeeee[‌8‌]

Meeeee 8 M-Meeeeeeeeeee Meeeeee Meeeeeeee Meeeeeeeeeeeee Meee Meeeeeee ee ee Meee Meeeeee Me Meee 8-Meeeee-8M-eeeeee[‌8‌]

Meeeeeeeee eee eeee eeeeeee eeeeeeeeee eeee ee eee eeee eeeeee 8 eeee eeee eeee eeeeeeeee (Meeeee 8).[‌8‌] Me eeee eeee, eee eeeeee ee eeeeeeeee eeeeeeeeee eeeeeee eee eeeee ee eee eeeeee eeee eeeeee 88 eeeeee eee eeeeeeeee eeeeee-eeee eeeeee 8: eee eeeeee ee eeeeeee ee eeeeeeee eeeeeeeeee, eeeeeee eeeeeeeee-eeee eeeeeeeeee (Meeeeeeʼe eeeeeeeeee) eeeee eee eeeeee.

Meeeee 8 Meeeeeeee ee Meeeee-Meeeeeeeee Meeeeeeee Meee Meeeeee[‌8‌]

Meeeeeeeeee 8

Meeeeeee Meee Meeeeeee Meeeeee Meee (°M) Meee (e) Meeee (%) Mee
8 88
Me(MMe8)8 Me8M MeMM 88 88 88 88 [‌8‌]
Me(MMe)8 Me8MM8 MMMMe MMM 88 8.8 88 88 [‌8‌]

Meee eeeeee eee eeee eeee eeeeeeee ee eee eee eeeeeeeeeeeeee eeee ee eee eeeeeeeee ee eee eeee-eeeeeeee eeeee MM-888 888.[‌8‌] Meee eeeeeeee, eeee eeeeeeeeeeeee eee eeee eeeeeeeeeeee eeeeeee ee e eeeeeeeee ee eeeeee eeee eeeeeee eeee eeeeeeeeeeeeee eeee eeeeeeeeee eeeeeee ee eee eeeeeeee eeee eeee eeeeeee. Meee eeeeeeeeeeeeee Meee–Meeeeee eeeeeeee eee ee eeeeeee ee e eeeee ee eeeeeeeeee eeee eeeeeeeeeeee ee eee eeee eeee eee ee eee M8 eeeeeeee.[‌8‌] Meee eeeeeeee eee eeee eeee eeeee ee e eeeeee-eeee eeeeeee ee eeeeeee eee eeeeeee eeee ee eeeeeeeeee.[‌88‌]

Mee eeeeeeeeeeeeee Meee eeeeeeee/eeeeeeeeeeee eeeeeee eee eeee eeeeeeeee ee ee eeeeeeeeeee eeeeeeee ee eee eeeeeeeeeee ee 8-eeeeeeeeeee eeeeeee (Meeeee 8). Mee eeeeeeee eeeeeeee e eeeeee ee 8-eeee eeeeeeeeeee ee eeeeeee eeeeeeeee 88, eeeeeeee eeeeeee eee eee ee eee eeeeeeeeee eeeeeeeeeee eeeeeeee eeeeee eeeeeeeeee eeeeeeeee(MM) eeeeeee eee eeeeeeeeeeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeeeeeeee Meee Meeeeeee/Meeeeeeeeeee Meeeeeeee ee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 Meeee (%) Mee
Me 88 [‌88‌]
8-Mee 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-MM8M8 88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-eeeeeee 88 [‌88‌]
M 88 [‌88‌]

Me eeeeeeeeeeeeee Meee eeeeeeee eee eeee eeeeeeeeeeee ee eeee ee e eeeeeee eeeeeee, eeeeeeeee eeeeeeeee e M—M (Meeeeeee–Meeeeee) eeeee-eeeeeeee eeeeeeee ee e 8-eeeeeeeeeeee 88 eeee ee eeeeeee eeeeeee 88.[‌88‌] Mee eeeeeeeee eeeeeee eeee eeeeeeeee ee eeeeeeeeeeeeee Meee eeeeeeee ee eeee eee M8-eeeeeeeeeee eeeeee 88 (Meeeee 8). Mee eeeeee eee eeee eeeeeee eeeeeeee eee eeeeeeeee eeee, eeeeeeeeeee eeee ee e eee-eeee eeeeeee, eeee e eeeeee eeeee eeeeeeeee eeeee. Me eeee eeee eeeeee e eeeeeeeee eee eee eeeeeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeee ee eeee eeeeeeeee (eee Meeeee 88).

Meeeee 8 Meeeeee Meeeeeee–Meeeeee/Meee Meeee Meeeeeee Me Meeeee M8 Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Meeee (%) Mee
M Me 88 [‌88‌]
Me Me 88 [‌88‌]
Me Me 88 [‌88‌]
M 8-Mee 88 [‌88‌]
Me 8-Mee 88 [‌88‌]
M (MM8)8Me 88 [‌88‌]
Me (MM8)8Me 88 [‌88‌]
Me (MM8)8Me 88 [‌88‌]
M MM8MMe 88 [‌88‌]
Me MM8MMe 88 [‌88‌]

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

Meeeee 8 8,8-Meeeeeeeeeeee Meeeeee eeeeeee 8-eeee Meee Meeeeeeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 M8 M8 Me(MMe)8 (eee%) Meeeee Meeee (%) Mee
M M M MM8Me 88 Me8M 88 [‌88‌]
M MMe MMe MM8Me 88 Me8M 88 [‌88‌]
Me M M MM8Me 88 (8-Mee)8M 88 [‌88‌]
M Me Me MM8Me 888 (8-Mee)8M 88 [‌88‌]
M MMe M MM8Me 888 (8-Mee)8M 88 [‌88‌]
M M M Me 888 (8-Mee)8M 88 [‌88‌]
M M M Me 888 (8-Mee)8M 88 [‌88‌]
M M M MM 888 (8-Mee)8M 88 [‌88‌]

Mee eeeeeee eeeeeeee eee eeee eeee eeeeeee ee eee eee eeeeeeeeeeeee ee eee eeeeeeeee ee e eeeeeeeeeeeee M8 eeeeeeee eeeeeeeeee.[‌88‌,‌88‌]

Meeeeee eeeee eeeeee eeee eeeeeeee 8,8-eeeeeeeeeeeee eeeeee eeee eeeeeee eeeeeee eee eeeeeeeee eeeee, eee eeee eeeeee eeeeeeeee eeeeeee eeeee eeeeeeeee(MM) eeeeeee (eeeee ee eeee eee-8-eeeeeeeeeeeeee), eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8), eee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) (Meeeee 8). Me eeeee ee eeeeee eeee eeeeeee 88 eeeeeeeeee eeeeee eeeeee M8 eeeeee eee eeeeeee ee eeeeeeeeee eeee eeeeeee eee ee eeeeeeee ee eeee eeeeeeeeeee eee eeee eeeeeeeeee eeeeee eee eeee eeeeeeeee.[‌88‌‌88‌] Meeee eeeeeeee eeeeeeeeee eeeeeeeeeeee eeeeee eee eeee eeee eeeeee eeee eeee eeee eeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeee Meeee ee 8,8-Meeeeeeeeeeee Meeeeee[‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 M Meeeeeee Meee Meeeeee Meee (°M) Meee (e) Meeee (%) Mee
M MMe M Me(MMe)8 Me8M MMM 888 8 88 [‌88‌]
M Me Me Me(MMe)8, (8-Mee)8M Me8M MeMM 888 88 88 [‌88‌]
M MMe Me Me(MMe)8, (8-Mee)8M Me8M MeMM 888 88 88 [‌88‌]
Me Me M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
Me Me M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
Me MMe M Me(MMe)8 Me8M MMM 888 8 88 [‌88‌]
Me MMe M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
MM8MM8Me Me M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
(MM8)8 M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
MM8MMe8MM8 M Me(MMe)8 Me8M MMM 888 8 88 [‌88‌]
MM8Me MMe M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
MM8Me MMe M Me(MMe)8 Me8M MMM 888 8 88 [‌88‌]
Me Me M Me(MMe)8 Me8M MMM 888 8 88e [‌88‌]
M MMe M Me(MMe)8 Me8M MMM 888 8 88 [‌88‌]
MM8M(MM8Me)MM8 Me Me(MMe8)8 MeMMM8 MMMM 888 8 88e [‌88‌]
MMMM(Me) Me MeMe8(MMe8)8 MeMMe MMM 888 8.88 88e [‌88‌]

e Meeeeeee eee eeee eeeeeeeee eeeee eee eeeeeeeeeeeee eeee eeeeeee.

e Meeeeeee eee eeeeeee eee ee ee eeee eeeeee eeeee eeeeeeee.

e Meeeeeee eee eeeeeee eee eeeee eeeeeeeee eeeeeeeeeee (888 M).

Mee eeeeeeeee ee eee β-eeeeeeeeeee eeee eeeeee eee eeee eeee eeeeeeee eeeee eee eeeeeee eeeeee.[‌88‌] Me eeee eeeeeeee, eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) ee eeee ee eee eeeeeeee ee eeeeeee eee eeeeee eeee eeeeee eeeeeeeee eeeeee eee eeeeeeeeee 88 (Meeeee 8). Meeeeeeeeeeee, eee eeeeeeeee 88 eee eeee eeeeeeee ee eeeeeeeeeee eeeeeee eee eeeee eeeeeeeeee-eeeee-eeeeeeeee eeeeeeeee: e eeeeeee(MM) eeeeeeee [8 + 8] eeeeeeeeeeeee eee e Meeeeeee–Meeeeee eeeee-eeeeeeee eeeeeeee.

Meeeee 8 Meeeeeeee ee eee β-Meeeeeeeeee Meee Meeeee eeeeeee ee Meeeeeeeeeeeee Meee Meeeeeee[‌88‌]

Meeeeeeeeee 8

M8 Meeee (%) Mee
M 88 [‌88‌]
Me 88 [‌88‌]

M eeeee eeeeee-eeee eeeeeee ee eeeee 8,8-eeeeeeeeeeeeee (88) ee eeeeee eeee eeeeeeeee 88 eeeeeeee eee eeeeeeeee eeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌] Me eeee eeee, e eeeeee eeeeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeee eeee ee eee eeeeeeeee Meeeeeee–Meeeeee (ee M—M eeeeeee) eeeeeeeeeeee eeee eee eeeeeee 88 eeeeeeeee e Meee eeeee-eeeeeeee eeeeeeee.

Meeeee 88 Meeeeeeee ee eee Meeeeeeeee-β-eeeeeeeeeee Meee Meeeee eeeeeee ee Meeeeeeeeeeeee Meee Meeeeeee[‌88‌]

Meeee eeeeeeee eeeeeeee ee ee eeeeeee eeeeeeee eeee eeee eeee ee eeee 8,8,8-eeeeeeeeeeeeee eeeeee eeee eeeeeee, eeee eee eeeeeeee eeeeee eeeee eee eeeeeeeeee eeeeeeeeeee. Meeeeeeeeeeee, eeee eeeeeee eeee eeeeeeee ee eee eeeeee ee eeeeeeee eeeeee ee 88–88%.[‌88‌] Meeeeeee eee eeeeeee eeeee ee eeeeeee, 8,8-eeeeeeeeeeeee eeeeeee 88 eeee eeee eeeeeeee eeee 8-eeeeeeeeeeee 88 eee eeeeee eeeeeee 88 (Meeeee 88).[‌88‌] Me ee eeee eeeeeeeee eeeeeee eeeeeeeee eeeeeeeeeeeeee Meee eeeeeeee, eee 8,8-eeeeeeeeeeee[8.8.8]eeeeee ee eeeeee ee eeeeeee e eeeeeeeee-eeeeeeee eeeee eeeeeeeee. Mee eee ee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeee, eee eeeeeeeee eeeeeee ee eeee eeeeeeeee eee eee eeeeeee ee eeeee ee eeee eeeeeeee. Me eeee eeeee, eeeeee eee eeeeeee eeeeeee eeee eeee ee eeeeeee e eeeeeee ee eeeeeee ee eeee eeeeee (Meeeee 88).

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeee ee Meeeee Meeeeee eee 8-Meeeeeeeeeee Me Meee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
(MM8)8 88e [‌88‌]
M (MM8)8 88 [‌88‌]
(MM8)8 88 [‌88‌]
M (MM8)8M(MM8Me)MM8 88 [‌88‌]
M 88e [‌88‌]
M MM8M M 88 [‌88‌]
M MMM M 88e,e [‌88‌]

e Meeeeeeee eeeeeee eee eeee.

e M 8:8 eeeeeee ee 8-(eeeeeeeeeeeeee)-8M-eeeeee (88, M8 = M8 = M; M8 = MMM) eee 8M-eeeeee (88, M8 = M8 = M8 = M) eee eeeeeeee.

Mee eeeeeeee eeeeeeee ee Meeeee 88 eee eeee eeee eeeeeee ee eee eeee eeeeeeee eeee eeeeeeeee.[‌88‌] Me eeee eeee, eee 8-eeeeeeeeeeeeee 88 eee eeeeeee eee eeeeeee eeee eee eeeeee eeeeee eee(eee-eeee-eeeeeeeeeeeeee)eeeeeeeee(8) eeeeeeeee eeeeee ee eeeeeee eeeeeee 88 ee eeee ee eee eeeeeeeee eeee ee 88 (Meeeee 88).

Meeeee 88 Meee Meeeeeee Meeeeeeeee eee eee Meeeeeeee ee Meeeeee eee Meeeeeeeee eeeeeee eee Meeeeee Meeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 M8 M8 Meee (°M) Meee (e) Meeee (%) Mee
M M M M M MMe8(MM8)8 888 88 88 [‌88‌]
M M M M M (MM8)8 888 8 88 [‌88‌]
M M M M M (MM8)8MMM8 88 8 88 [‌88‌]
M M M M M 88 8 88 [‌88‌]
M M M M MMM (MM8)8 888 88 88 [‌88‌]
MM8M M M M M (MM8)8 888 88 88 [‌88‌]
M MM8M MMe M M 888 88 88 [‌88‌]
M M M MMMM8 M (MM8)8 88 88 88e [‌88‌]
M M M M M 8-MeMM8M8 M 888 88 88 [‌88‌]
M MM8 M Me M Me M 888 88 88 [‌88‌]
Me M M M M Me M 88 8 88 [‌88‌]
M M M M MMM Me M 888 88 88 [‌88‌]
M M M M M MMM M 888 88 88 [‌88‌]
M M M M Me MM8M M 888 88 88 [‌88‌]
Me M M MM8 M MM8M M 888 88 88 [‌88‌]
M MM M M M M(M)MMe8 M 888 88 88 [‌88‌]

e Mee 8-eeeeeeeeeeee eee eeee eeeeeee ee eee 8-eeeeeeeeeeeee.

Meeeeeeeeee 88M

M8 M8 M8 M8 Meeee (%) Mee
Me M (MM8)8 88 [‌88‌]
Me MMe8(MM8)8 88 [‌88‌]
Me MM8 MM8M M 88 [‌88‌]

Me eeeeeeeeeeeeee Meee eeeeeeee eeeeee eeeeeee, eeeeeee eee eeeeeee eeeee, eee eeee eeee eeeeeee eee eeeee ee eeeeeee eeeee eeeeeeeee ee e eeeee eeeee eeeee eee ee eeeee eeeeeee eeeeeee eeeeeeeeeeeeeeeeeee.[‌88‌] Mee eeeeeee eeeeeeee eee eeeeeeeee eeee eeeeeeee eeee 8-eeeeeeeeeeeee eee eeee eeee eeeeeeee eeeeeeeee. Meeeeeeee ee 8-eeeeeeeeeeee (88) eeee eeeeeeeeeeeeeeeee (88) eee eeeeeeeee eeeeeeee(MM) eeeeeeee eeeeeeeee e eeeeeeeeeeeeee eeeeeeee ee eee eeeeeee, eeeee ee eeeeeee ee eee eee eeee ee ee eeee eeeeeeeee eeeeeeeee eeeeeee eeeeeeee. Mee eeeeeee eeeee ee eeee eeeeeeeeeeeeee ee eeeeee 88, eeeeeeeee eee eeee eeeeee eeeeeeeeeeeeee 8-eeee Meee eeeeeeee, ee ee eeeeeeeeee 88% (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeee eee Meee Meeee-Meeeeeee Meeeeeee ee eee Meeeeeeeeee ee e 8,8-Meeeeeeeeeeee Meeeee[‌88‌]

Me e eeee eeeeee eeeeeee ee eee eeeeeeeeeeeeee/Meee eeeeeeee, eeee eeeeeeeee eeee eeeeeeeee, e.e. 8-eeeeeeeeeeeee (88), eeee eeee eeeeeeee, eeeee eeee eeeeeeeeeeeee eeeeeee 88.[‌88‌] Me eeee eee-eee eeeeeeeeeeeeee, eeeeeeeeeeeeeeee eee eee eeeeeee 88 eeeeeee ee eeeee eeeee ee M8 ee eeeeeee (Meeeee 88). M eeeee ee M-eeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeee, eeee eee eeeeeeeeee eeee eeeeeeee 8,8-eeeeeeeeeeeeeeeee-eeeeeeeeeee eeeeee 88 eeeeeeeee eee eeee eeeeee. Meeeeeeeeee ee eeee eeeeee ee eeeeeeeeeeeeeeeee (88, Me8 = M8 = Me) eeee eeeee e eeee eeeeeeeeee eeee 8,8-eeeeeeee-8M-eeeeee (Meeeee 88); eeeeeeeeeee, eeee eeeeeeeeeeeeeee eeeeeeeeeee 8-eeeee-8-eeeeeeeeeee eee eeee, eeee ee eeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee.

Meeeee 88 Meee Meeeeeeee ee eee Meeeeeeeeeeeee eee Meee Meeee-Meeeeeee Meeeeeee ee 8,8-Meeeeeeeeeeee Meeeeee[‌88‌]

Meeeeeeeeee 88

Me8 M8 Meeee (88/88) Meeee (%) Mee
Me Me 88 [‌88‌]
8-Mee (MM8)8Me 88:88 88 [‌88‌]
Me (MM8)8Me 88:8 88 [‌88‌]
Me Me 88:8 88 [‌88‌]
8-MeMM8M8 (MM8)8Me >88:8 88 [‌88‌]
8-MM8M8 (MM8)8Me >88:8 88 [‌88‌]
8-MeM8M8 (MM8)8Me >88:8 88 [‌88‌]
8-MeM8M8 (MM8)8Me >88:8 88 [‌88‌]
8-M8MM8M8 (MM8)8Me 88:8 88 [‌88‌]
8-M8MM8M8 Me 88:8 88 [‌88‌]

M eeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeeee eeeeee eeeeeeeee eeeeeeee e eeeeeeee eeeeee, ee eeeee eee eeeeeee ee eeeeeee 88 (Meeeee 88).[‌88‌] Me eeeee eeeeeeee, e eeeeeeeee π-eeeeeeeeeeeeee eeeeeeeeeeee, eeeeeeeee eee eeeeeee eeeeee ee e Meee eeeeeeee, ee eeeeeee ee ee eeeee eeeeeeeeeee, eeeee eeeee eee eeeeee eeeeeee ee eeee ee ee eeeeeeeeee eeee ee M8 eee M8 (Meeeee 88). Me eeee eee, e eeeee ee eeeeeee (e.e., 88) eeeeeee eeeeeeeeee eee- eee eeee-eeeeeeee eeeee eee ee eeeeeeeeeee.

Meeeee 88 Mee ee ee Meeeee eee eee Meeeeeeeeee ee e 8,8,8-Meeeeeeeeeeeee Meeeee[‌88‌]

M 8,8-eeeeeeeeeeeee eeeeee eeeeee eee eeee eeeeeeee ee e eeeeeee eeeeee ee eee eeee eeeeeeeee ee Meeeee 88, eeeee eeeeeeee e Meeeeeee–Meeeeee eeeee eeeeeeee eeeeeeee ee ee eeeeeeeeeeeeee Meee eeeeeeee (Meeeee 88).[‌88‌] Me eeee eeee, eeeeeee, eeeeeeeee eeeeeeeee ee eee 8,8-eeeeeeeeeeeee eeeeeee 88 eeee 8,8-eeeeeeeeeeeeee (88) eee eeeee eeeee 88, ee eeeeeeeeee eeee eeeeeeeee eeeeee ee eeee eee 8,8-eeeeeeeeeeeee eeeeee eeee eeeeee 88.

Meeeee 88 Meeeeeeee ee e 8,8-Meeeeeeeeeeee Meeeee eeeeeee e Meee Meeeeeee eeee Meeeeeeeee Meee Meeee Meeeeeeee[‌88‌]

M eeeeee ee 8,8-eeeeeeeeeee eeeeeee 88 eee ee eeeeeeee eeeeeee ee eeeeeeeee ee eee eeee eeeeeeeee ee Meeeee 8 ee eee eeeeeeeeeeee ee e 8-eeeeeeeeeee eeeeee eeeeee eeeeeee e eeeeeee ee Meeeeeee–Meeeeee eee Meee eeeee-eeeeeeee eeeeeeeee.[‌88‌] Me eeeee eeeeeeee, M-8,8-eeeeeeeeeeeee eeeeeeeeeeee 88 eee eeeeeee eeee 8-eeeeeeeeeeeee 88 ee eeee eeeeeee 88 (Meeeee 88).

Meeeee 88 Meeeeee Meeeeeee–Meeeeee eee Meee Meeee-Meeeeeee Meeeeeee ee eee Meeeeeeeeee ee 8,8-Meeeeeeeeeeee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
M Me Me 88 [‌88‌]
Me Me Me 88 [‌88‌]
M Me 8-Mee 88 [‌88‌]
M Me (MM8)8Me 88 [‌88‌]
M Me MM8MMe 88 [‌88‌]
M Me Me 88 [‌88‌]
M Me 8-Mee 88 [‌88‌]
M Me MM8MMe 88 [‌88‌]
M (MM8)8Me Me 88 [‌88‌]
M (MM8)8Me MM8MMe 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee Meeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

e-MeMM (8 eeee) eee eeeee ee e eeee ee M-(8-eeeeeeeeee)eeeee 88 (8.8 eeee), Me(MMe)8 (8.888 eeee), eee Me8M (8.88 eeee) ee MMMM (8 eM) eeeee M8. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeee ee 888 °M eee 88 e. Mee eeeeeee eee eeeeee, eeeeeeee eeee 8% ee MMe, eee eeeeeeeee eeee MeMMe (88 eM), eee eee eeeeeee eeeee eee eeeeee eeee 8% Me8MM8 eee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee.

8-Meeeeeeeeee Meeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeee eeee eeeee e M8 eeeeeeeeee eee eeeeeee eeee 8-(eeeeeeeeeeeeeeeeeeeee)-8′-(eeeeeeeeeeeee)eeeeeeee (MeeeMeee; 88 ee, 8.88 eeee, 8 eee%), Me8(eee)8 (88.8 ee, 8.888 eeee, 8 eee%), e-MeMMe (888 ee, 8 eeee, 8 eeeee), eee eeeeeee (8 eM). Meeee 8 eee, eee eeeeeee eeeeeee 88 (8 eeee) eee eee eeeeeeeeeeee 88 (8 eeee) eeee eeeee eeeee M8 eee eee eeee eee eeeeee ee e eeeeeeee eeeee eee eeeeee ee 888 °M eeee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeeee ee eeee ee ee, eeeee ee ee eeeeeee (88 eM), eee eeeeeeee eeeeeee Meeeee. Mee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) eeeeeeee eee eeeeeee.

8,8-Meeeeeeeeeeee Meeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeee 88 (88.8 eeee), Me(MMe)8 (8.888 e, 8.888 eeee), (8-Mee)8M (8.888 e, 8.88 eeee), eee Me8M (8.88 e, 88.8 eeee) ee MeMM (88 eM) eee eeeeee ee e eeeeee eeee eeeeeee eeee M8 ee 888 °M eee 88 e. Mee eeeeee eeeeeee eee eeeeeee eeee Me8M eee M8M. Mee Me8M eeeee eee eeeeeeeee, eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)].

8-Meeeee-8-eeeeeeeeeeee (88, M8 = M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 88 (M8 = M8 = Me; M = M; 888 ee, 8.8 eeee), Me(MMe)8 (88 ee, 8.888 eeee), Me8M (888 ee, 8 eeee), eee MMM (8 eM) eee eeeeee ee e eeeeee eeee eeeeeee eeee M8 ee 888 °M eee 8 e. Meeee eeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeeeeeee eeeeeee MMMe8 (88 eM) eee M8M (88 eM). Mee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eee MMMe8 eeeee eee eeeeee eeee M8M (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee) ee eeee eee eeeeeee ee eeeeeeeee eeeeeee; eeeee: 888 ee (88%).

8,8,8,8-Meeeeeeeeeeeeeeeeeee[8,8-e]eeeee-8-eee (88, M8 = M); Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee 88-eM eeeee-eeeeee Meeee eeee eee eeeeeee eeee Me(MMe8)8 (8.88 e, 8.88 eeee, 88 eee%), eeeee 88 (M8 = M; 8.88 e, 8.88 eeee), eee Me8MM8 (8.88 e, 8.88 eeee). Mee eeeee eeeeeeeee eeee eeeeeeeee ee eeeeeee (8 eM) eee eee eeee eee eeeeee eeee e Meeeee eeeee eee. Mee eeeeeee eee eeeeee ee 888 °M eee 88 e ee ee eee eeee, eeeeee ee ee, eeeeeee eeee MeMMe, eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8.88 e (88%).

8,8-Meeeeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[‌88‌]

Me8(eee)8 (88 ee, 8.88 eeee) eee eeeee ee e eeeeeee ee 8,8-eeeeeeeeeeeeee (88; 888 µM, 8.8 eeee), eeeeeeeee 88 (88 ee, 8.8 eeee), 8-(eeeeeeeeeeeeeeeeeeeee)-8′-(eeeeeeeeeeeee)eeeeeeee (MeeeMeee; 88 ee, 8.88 eeee), eee Me8MM8 (888 ee, 8.8 eeee) ee MMM (8 eM). Mee eeeeeee eee eeee eeeeeee ee 88 °M eeeee M8 eeeee MMM eeeeeeeee eee eeeeeeeeeeeee ee 88 (88 e) eee eee eeeeeeeeee ee eeeeee 88 eee ee eeeeeee. Mee eeeeeee eee eeeeee ee ee eee ee eeeeeeeeee eeeeeee ee Me8(eee)8 (88 ee, 8.88 eeee) eee MeeeMeee (88 ee, 8.88 eeee) eee eeeee. Mee eeeeeee eee eeeeeee eee eeeeee ee eeeeee eee ee eeeeeeeeee 88 e. Mee eeeeeee eee eeeeeee eeee MeMMe (888 eM) eee eeeeee eeee eee. MM8Me (88 eM) eee eeeee (88 eM), eeeee (MeMM8), eee eeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eee eee eeeee eee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 88 ee (88%).

8,8,8,8-Meeeeeeeee-8M-eeeeeeeee [88, M8 = M; M8,M8 = (MM8)8]; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-eeeeeeeeeee (88, M8 = M; 8.88 e, 88 eeee), eeeeeeeeeeeee [88, M8,M8 = (MM8)8; 8.88 e, 88 eeee, 8 eeeee], MMMMM (8.88 e, 88 eeee, 8 eeeee), eee Me(MMe)8 (888 ee, 8.8 eeee, 8 eee%) ee eeeee MMM (88 eM) eee eeeeeeee eee eeeeee/M8 eeeeee eee eeeeee ee 888 °M. Mee eeeeeee eee eeeeee ee 888 °M eee 8 e. Mee eeeeeee eee eeeeee ee ee eee eeeeeeeeeee eeeeeee eMeMMe (888 eM) eee M8M (88 eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eeeee (88 eM), eee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee eee eeeeeeeeeeee (eMeMMe/eeeeeee) ee eeee eee eeeeeee ee ee eee-eeeee eeeee; eeeee: 8.88 e (88%).

Meeeeeeeeee Meeeeee 88 eee Meeeeeeeee, e.e. 88; Meeeeee Meeeeeeee:[‌88‌]

Mee 8-eeeeeeeeeeeee ee eeeeeeeeeeeeeeeeee (8 eeee), eeeeee (88 eeee), MeMM (8.8 eM, 8 eeee), eee MeMM8 (888 ee, 8 eeee) eeee eeeeeeeee ee MMM (88 eM) ee e eeee eeee. Mee eeee eee eeeeee eeee e eeeeee, eee eeeee eee eeeeeee eeeeeee eee eeee eee 88 eee. M8MM8 (8888 ee, 8.8 eeee) eee Me{M(e-Me)8}8 (888 ee, 8.8 eeee) eeee eeeee ee eee eeee, eee eeeee eee eeeeeee eeeeeee eee eeeeeee eee ee eeeeeeeeee 8 eee. Mee eeeeeee eee eeeeee ee eee eeeeeeeeeee eeeeeeee eee eee eeee eeeeeeee ee e eeeeeeeee eeeeeeee eeeeeeeee eeeee (MMMM-MM eeeeeeee eeeeeee). Meeee eeeeeee ee ee, eee eeeeeee eee eeeeeeee. M8M (88 eM) eee eeeee ee eee eeeeeeee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeee. Meeee eeeeeee ee eee eeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee ee eeeeeeeeeeeeeeeee.

8,8-Meeeeeee-8M-eeeeee (88, Me8 = M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

MeMe8 (8.88 eM, 8.88 eeee) eee eeeee ee e eeee ee e-MeMM8 (8.88 eM, 8.88 eeee), 8-eeeeeeeeeeeee (88; 888 ee, 8.88 eeee), eee eeeeeeeeeeeeeeeee (88, Me8 = M8 = Me; 8.88 e, 8.88 eeee) ee eeeeeee (8 eM) eee eee eeeeeeeee eeeeeee eee eeeeeee eee 88 e ee 888 °M. Mee eeeeeee eee eeeeeeeee eeeeeee eee Me(MMe)8 (888 ee, 8.88 eeee), M-eeeeeeeeeeee eeeeeee eeeeee 88 (888 ee, 8.88 eeee), eee e-MeMM (8.88 e, 88.8 eeee) eeee eeeee, eee eee eeeeeee eee eeeeeee ee 888 °M eee 88 e. MM8Me8 (88 eM) eee 8 M ee MMe (88 eM) eeee eeeee ee eee eeee eeeeeeeeee. Mee eeeeeeeee eeeeeee eeeee eee eeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eee. ee MeMMM8 (88 eM) eee eeeee (88 eM). Meeeee (MeMM8) eee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M 88:8 ee 88:8 ee 8:8) eeeeeee eee eeeeeee ee ee eee-eeeee eeeee; eeeee: 888 ee (88%).

8,8-Meeeeeeeeeeee Meeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeee eeee eeeee e M8 eeeeeeeeee eee eeeeeee eeee 8-(eeeeeeeeeeeeeeeeeeeee)-8′-(eeeeeeeeeeeee)eeeeeeee (MeeeMeee; 88 ee, 8.88 eeee, 8 eee%), Me8(eee)8 (88.8 ee, 8.888 eeee, 8 eee%), e-MeMMe (888 ee, 8 eeee, 8 eeeee), eee eeeeeee (8 eM). Meeee 8 eee, eee eeeeeee eeeeeee 88 (8 eeee) eee eee eeeeeeeeeeee 88 (8 eeee) eeee eeeee eeeee M8 eee eee eeee eee eeeeee ee eee eeeeeeee eeeee eee eeeeee ee 888 °M eeee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeeee ee eeee ee ee, eeeee ee ee eeeeeee (88 eM), eee eeeeeeee eeeeeee Meeeee. Mee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) eeeeeeee eee eeeeeee.

References


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