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1.1.1.1.3.1.1 Coupling of Arenes with Haloarenes

DOI: 10.1055/sos-SD-217-00003

Melkonyan, F. S.; Gevorgyan, V.Science of Synthesis: Catalytic Transformations via C—H Activation, (2015121.

A variety of dibenzofurans 53 can be synthesized from 1-halo-2-phenoxybenzenes 52 (Scheme 18). For example, 1-bromo-2-phenoxybenzenes 52 (X = Br) undergo intramolecular C—H arylation to form dibenzofurans 53. The reaction is catalyzed by palladium(II) acetate (10 mol%), does not require any ligands, and the scope is mostly limited by the availability of the starting materials. Importantly, this is an efficient transformation for the synthesis of dibenzofurans bearing sensitive functional groups in spite of the harsh reaction conditions.[‌84‌] Furthermore, 1-iodo-2-phenoxybenzene (52, X = I; R1 = R2 = R3 = H) has been converted into the corresponding dibenzofuran in almost quantitative yield. In this case, the reaction (which operates at lower temperature) is catalyzed by a palladium(II) acetate/tricyclohexylphosphine catalyst in conjunction with silver(I) carbonate as an additive.[‌87‌] Finally, less reactive 1-chloro-2-phenoxybenzene (52, X = Cl; R1 = R2 = R3 = H) has been reported to undergo efficient intramolecular C—H arylation using a palladium catalyst with an N-heterocyclic carbene ligand.[‌95‌] As well as with halo-substituted benzenes, arylation is also possible with the corresponding 4-toluenesulfonates to give the corresponding dibenzofurans (see Section 1.1.1.1.3.1.2).

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

M M8 M8 M8 Meeeeeeeee Meeee (%) Mee
Me M M M Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me MM8 M M Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me M MM8 M Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me M M MM8 Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me M M MM Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me M M MM8MM Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me M M MM8M Me(MMe)8 (88 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
M M M M Me(MMe)8 (8 eee%), Me8M•MMM8 (8 eee%), Me8MM8 (8.8 eeeee), MMM, 888 °M 88 [‌88‌]
Me M M M Me(MMe)(MMe)8(MM8) (8 eee%),e MMMeMe (8 eee%),e M8MM8 (8 eeeee), MMM, 888 °M 88 [‌88‌]

e MMe = 8,8-eee(8,8-eeeeeeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeeeeee-8-eeeeeee.

Mee 8-eeee-M-eeeeeeeeeeeeee 88 eee ee eeeeeeeeeee eeeeeeeee eeee 8M-eeeeeeeeee 88 (Meeeee 88).[‌88‌,‌88‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeee(MM) eeeeeee (8 eee%) ee eeeeeeeeeee eeee eee eeeee, eeeeeeee-eeee eeeeeeeeeeeeeeeeeeeeee eeeeee. Mee eeeeeeee eeeeeeeeee eee eeeeee eeee eeeee eeeeeeee eeeeeeeee eee eeeeeeeee eeeeeeeee[‌88‌] eee eeeeeeeee eeeeeee ee eee eeeeeeee. Meeeeeeeeee, eee M—M eeeeeeeee ee 8-eeee-M-eeeeeeeeeeeee 88 (M8 = M8 = M8 = M8 = M8 = M; M = M) eeeeeeee eee eee ee eeeeee(M) eeeeeeeee ee ee eeeeeeee ee eeeee ee eeee eee eeeeee eeeee eeee ee eeeeee eeeeee eee eeeeee ee eee eeeeeeee eee eeeee, eeeeeeeeee, eeeeee eeeeeeeee ee eee eeeeeeeee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee 8M-Meeeeeeeee ee M—M Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M M8 M8 M8 M8 M8 Meeeeeee Meeee (%) Mee
Me M Me M M M 88 [‌88‌]
Me M M M MM8 M 88 [‌88‌]
Me Me M Me M M 88 [‌88‌]
Me M M M M M 88 [‌88‌]
M M M M M M Me8MM8 (8.8 eeeee) 88 [‌88‌]

Meeeeeee eeeeeeeeeee 8M-eeeeeeeeee 88 eee ee eeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeee 88, eeeee eee ee eeee eeeeeeeeeee eeee 8-eeeeeeeeeeeeee 88 eee eeeeeeeeeee 88 eeeee eee eeeeeeee eeeeeeeeee (Meeeee 88).[‌88‌,‌88‌] Mee eeeeeeee eeeeeeee eee eeeeeee eeeeeeeeeeeeee eeeee eeeeeeee (Meeeeeee–Meeeeee eeeeeeeee) ee eeee eee eeeeeeeeeeee eeeeeeeeeeee 88, eeeeeeee ee eeeeeeeeeeeeee M—M eeeeeeeee ee eeeeeee eee eeeee 8M-eeeeeeeeee 88. Meee eee Meeeeeee–Meeeeee eeeeeeeee eee eee M—M eeeeeeeee eeeee eee eeeeeeeee ee eeeeeeeee(MM) eeeeeee/eee-eeee-eeeeeeeeeeeeee eeeeeeeee eeeeee eeee-eeeeeeee ee e eeee. Mee eeeeeeee ee eeeeeeeee eee eee eeeeeeeee ee 8M-eeeeeeeeee eeeeeeeeee eeeeeeeeeeee ee eeeeeee eeeeeeeeee eeeeee. Mee eeeeeeeeeeeee 88 eeeeeeeeee eee eeeeeeeee M—M eeeee eee eeeeeeeee, eee eeeeeeeeeee ee eeeeeeee ee eeeeee eeeeeee. Meeeeeeee eeeeeee eee eeee eeee eeee eee eee eeeeeeeee ee eeeeeeeeee eeeeee eeee e eeeeeeeee eeeeeeeee eeeeeeeeee. Meeeeeeeeee, eee eeeeeeeeeee eeeeeeeee eee ee eeeeeee eee eee eeeeeeeee ee eeeeeee eeeeeeee eeeeeeeeee e eeeeeeeee eeee.[‌88‌] Mee eee ee eeeeeeee-eeeeeeeeee 8-eeeeeeeeeeeeee 88 eee/ee eeeeeeeeeee 88 eeeeee eee eee eeeeeeeee ee eeeeeeeeeee eeeeeeeeee.[‌88‌] Meeeeeeeeeeee, e eeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeee eeeeeeeeee ee eeeeeee Meeeeeee–Meeeeee eeeeeeeee ee eeeeeeee (eee M—M eeeeeeeee) eeee 8,8-eeeeeeeeeeee (eee M—Mee eeeeeeeee) eee e eeeeeeeeee M—M eeeeeeeee ee eee eeeeee eeeeeeeeeeeee eee eeee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee 8M-Meeeeeeeee ee Meeeeeeeee Meeeeeee–Meeeeee Meeeeeeee eee M—M Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 M8 M8 Meeeeeeeee Meeee (%) Mee
Me M M M M M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeee, 88 e 88 [‌88‌]
Me M M M M MMe M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeee, 88 e 88 [‌88‌]
Me M M M M MMe M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeee, 88 e 88 [‌88‌]
Me M MM8 M M MMe M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeee, 88 e 88 [‌88‌]
M M M M Me M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M M M MMe M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M M M Me M Me Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M Me M M Me M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M Me M M MMe M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M MMe M MMe M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M M M Me M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M M M Me M Me Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M M M MMe M MMe Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M M M M Me M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]
M Me M M M M M Me(MMe)8 (8 eee%), e-Me8M•MMM8 (8 eee%), e-MeMMe (8 eeeee), eeeeeee, eeeeeeeee, 888 °M, 8 e 88 [‌88‌]

Mee 8M-eeeeeeeeee 88 eee ee eeeeeeeeeee eeee 8-eeeeeeeeeeee 88 eee 8-(eeeeeeeeeeeeee)eeeeee eeeeeeeeeeeeeeeeeeeeeeeeee 88 eee e eeeeeeeeee eee-eee, eee-eeee eeeeeeeee (Meeeee 88).[‌888‌] Mee eeeeeeee ee eeeeeeeee ee ee eeeeeee eeeeeeeee ee (8-eeeeeeeeee)eeeeeeeeeeee 88, eeeeeeee ee eeeeeeeeeeeeee M—M eeeeeeeee ee eeeeeee eee eeeee 8M-eeeeeeeeee 88. Mee eeeeeeeee eeeeeeeee eeeeee eeeeeeee eee eee ee eeeeeeeee(MM) eeeeeee ee eeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee ee e eeeeee. Meeeeeeeeee, eeeee eeeeeeeee eeeeeeeee, eeee ee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM), eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8), eee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) eeeeeeeeeee eeeeeeeeee eeeeeeeeee. Meee eeeeeeeeeee eeeeee eee eee eeeeeeeee ee M-eeeeeeeeeee (MM) eeeeeeeeee ee eeee ee M-eeeeeeeeeee eeeeeee. Meeeeee, eeee eeeeee ee eeee eeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeee. Mee e eeeeeee eeeeeeeee ee eeeeeeeeee eeeeeeeee eeeeeeeee eeeeeeeee eee Meeeeee 8.8.8.8.8.8.8.

Meeeee 88 Mee-Mee, Mee-Meee Meeeeeeee ee 8M-Meeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeee (%) Mee
M M M M 88 [‌888‌]
M Me Me M 88 [‌888‌]
M Me Me Me 88 [‌888‌]
Me M M M 88 [‌888‌]
Me M M M 88 [‌888‌]
MM8Me M M M 88 [‌888‌]

M eeeeee ee eeeeeeee eeeeeeeeeeeee 88 (eeeeeeeeee) eee ee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeee(eeeeeeeeeee)eeeeeeeee 88 (Meeeee 88). Mee eeeeeeeeeeeeee M—M eeeeeeeee ee eeeeeeeee ee eeeeeeeee(MM) eeeeeee eeeee eeeeee-eeee eeeeeeeeee ee eeeeee eee eeeeeeee ee eeeeeeeeee ee eeee eeeeee. Meeeeeeeeeeee, eee eeeee ee eee α-eeeeeeeee, 8M-eeeeee[8,8-e]eeeeee 88 (M8 = M; M8 = M8 = M8 = MM), ee eeeee eeee eee eeeee eeeeeeeeee. Meee ee eeeeeeee eee ee e eeeeee eeeeeeeeeeee eeeeee ee eeeeeeeee ee eeeeeeeee eeee eee 8-eeeee eeeeee ee eeeeeeee. Meeeeeeeeee, eee eeeeeee ee eeeeeeeee eeeeeeeee ee eeee eeeeeeee eeeee ee, ee eee eeee ee eee eeeeeeeʼ eeeeeeeee, eee eeeee eeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeee(8)-eeeeeeeee M—M eeeeeeeee ee eeeeee eeeeee.[‌888‌]

Meeeee 88 Meeeee-Meee Meeeeeeee ee Meeeeeeee Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeee (%) Mee
M MM MM MM 88 [‌888‌]
MM M MM MM 88 [‌888‌]
MM MM M MM 88 [‌888‌]
MM MM MM M 88 [‌888‌]

M eeeeeee ee eeeeeeeeeee 8M-eeeeee[8,8-e]eeeeeee 88 (α-eeeeeeeeee) eee ee eeeeeeeeeee eeee 8-eeeeee-8-(eeeeeeeeeee)eeeeeeeee 88 (Meeeee 88). Mee M—M eeeeeeeee eeeeeeee eee eee ee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) ee eeeeeeeeeee eeee eee eeeee, eeeeeeee-eeee eee-eeee-eeeeeeeeeeeeee eeeeee, eeeee ee eeeee ee ee eeeeeeeee eee eee eeeeeeeee eeeeeeee ee eeeeeeeee eeeeeee eeee e M—Me eeee. Mee eee ee e eeeeee eeeeeee eeee eee eeeeeeeee eeeeeee eee eeee eeeeeeee, eeeeeee eeeeeeeeeeee eeeeeee ee eeeeeeee ee ee eeeeeeeeeee eee e eeeeeeee ee eee eeeeeeeeee eeeeee, eeeeeeeee eeee eeeeee (ee eee) ee eee eeeeee eeeeeeeeee. Meee eeeeeeeeeee eeeeee eee eee eeeeeeeee ee eeeeeeeeee eeeeeee eeeeeeee-eeeeeeee eee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee. Meeeeeeeeeeee, eee eeeeeeeeee eeee eee eeeeeeee eeeee ee M—M eeeeeeeee [88 (M8 = M8 = M8 = M8 = M; M8 = MMe) eee 88 (M8 = M8 = M8 = M8 = M; M8 = MM8Me)], eee eeeeeeeeeeeeee ee eeeeeeee ee eeeeee eeeeeee eeeeeeeeee ee eee eeeeeeeeee eeeeee ee eee M8 eeeeeeeeeee, eeeeeeeee eee eeeeeee ee eeee-eeeeeeeee (eeeeeeee ee M8) ee eeee eeee. Meeee eee eeeeeeee ee eeee eeeeeeeee ee eeeeee ee eee eeeeeeeee ee M-eeeeeeeeeeeee (MM) eeeeeeeeee, eee eeeeeee ee ee M-eeeeeeeeeee eeeeeeeee 88 (M8 = Me; M8 = M8 = M8 = M8 = M) eee eeee eeee eeeeeeee.[‌888‌] Meeeeeeee ee 8-eeeeee-8M-eeeeee[8,8-e]eeeeeee (8-eeeeee-8M-α-eeeeeeeeee) ee eeee eeeeeeee ee eeee eeeeeeeeeee.

Meeeee 88 Meeeeeeee ee 8M-Meeeee[8,8-e]eeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meeee (%) Mee
M M M M M 88 [‌888‌]
M M M MMe M 88 [‌888‌]
M M M MM8 M 88e [‌888‌]
M M M MM8Me M 88 [‌888‌]
M M MMe M M 88 [‌888‌]
M M MM8Me M M 88e [‌888‌]
M MMe M M M 88 [‌888‌]
M M M M MM8 88 [‌888‌]
Me M M M M 88e [‌888‌]

e Me(MMe)8 (8 eee%) eee e-Me8M (88 eee%) eeee eeee

e Me(MMe)8 (8.88 eee%) eee e-Me8M (88 eee%) eeee eeee.

e Me(MMe)8 (8 eee%) eee e-Me8M (88 eee%) eeee eeee eeee e eeeeee eeeeeeee eeee (88 eee).

Meeeeee eeeee-eeeeeeeeeee 8-eeeeee-8M-eeeeee[8,8-e]eeeeeee 88 (8-eeeeee-8M-α-eeeeeeeeee) eee ee eeeeeeeeeee eeee M-(eeeeeeeeeeee)-eeeeeeeeeee 8-eeeeee-8-eeeeeeeeeeeee-8(8M)-eeeeee 88 eee e eeeeee eeeeeeeeeeeeee (Meeee 8).[‌888‌] Mee eeeeee eeeeeeee ee eeeeeee eeeeeeeee-eeeeeeeee, eeeeeeeeeeeeee M—M eeeeeeeee eeee e M—Me eeee ee eeee eeeeeeeeeeeee 88, eeeee eeeeeeeeeeee eeeeeee eeeeeeeeeeeeee Meeeeeee–Meeeeee eeeeeeeee eeee eeee eeeeeee eee eeeeeeeee eeeeee ee eeee eee eeeeee eeeeeeeeee. Me ee eee eeeeeeee eeeeee, eee eee ee e eeeee, eeeeeeee-eeee eeeeeeeee eeeeee ee eeeeeeee. Mee eeeeeeeeee eeeeeeeeee eee eeeeeeeee eeeee eee M—M eeeeeeeee, eee eeeeeeee eeeeee ee eee eeeeeeeeee eeee eeeeeeeeee eeeeeeee. Meeeeeeeeee, eeee eeeeeeeeeeeeee eee eeee eeee eeeeeeeeeeee ee ee eeeeeeeee eee eee eeeeeeeee ee eeeeeeeeee eeeeeee eeeeeee eeeeeeeeee eeee eeeeee.

Meeee 8 Meeeeeeee ee 8-Meeeee-8M-eeeeee[8,8-e]eeeeeee[‌888‌]

Meeee Meeeeeeee Meeeeeee Meeeeee Meeee (%) Mee
Meeee Meeee
8 eeeeeeeeee Me8(eee)8 (8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 eeeeeeeeee Me8(eee)8 (8.8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 eeeeeeeeee Me8(eee)8 (8.8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 MeMMMe Me8(eee)8 (8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 MeMMMe Me8(eee)8 (8.8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 MeMMMe Me8(eee)8 (8.8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 Me(MM8)8MM8 Me(MMe)8 (8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 Me(MM8)8MM8 Me(MMe)8 (8.8 eee%), e-Me8M (88 eee%) 88 [‌888‌]
8 Me(MM8)8MM8 Me(MMe)8 (8.8 eee%), e-Me8M (88 eee%) 88 [‌888‌]

M eeee eeeeeee ee 8M-eeeeeeee[8,8-e]eeeeeee 88 eee eeeeeee eeeeeeeee eee eee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeee M—M eeeeeeeee ee M-eeeeee-eeeeeeeeeee 8-eeeeeeeeeeeee-8-eeeeee 88 (Meeeee 88).[‌888‌] Mee eeeeeeeeeeeeee eeeeeee eeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) ee eee eeeeeeee eee eeeeee eeeeeee ee eee eeee, eee ee eeee eeeeeeeee, eeeeeeeee eeeeeeeeeeee 88 eeeeeeeeee eeee eeeeeeee-eeeeeeee eee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee. Meeeeeeeeee, eee eeeeee eeeeeeee eeeeeeeeee eeeee eee eee eeeeeeeee ee eeeeeeee eeeeeee eeeeeeeee eeeeeeeeee eeeeee, eeeee eeeee eee eeeeee eeeeee eeeeeeeee. Meee ee eeee eeeeeeee eeeee, eee eeeeeeeeee eeee eeeee M—M eeeeeeeee ee eeeeeeee ee eeee eeee eee eeee, eee eeee-eeeeeeee M—M eeee eeeeee. Meeeeeeee eee eeeee ee eee eeeeeeee, eeeee eee eeeeeeeeee eeeeee eee eeeeeeeeeeeee M-eeeeeeeeeeeee eeeeeeeee-8-eeeeee, e.e. 88 (M8 = M), eeeeeeeee ee 8M-eeeeeeee[8,8-e]eeeeeee eeeeeeeeee eeeeeeeeeeee ee eeeeeeee eee eeee eeeeeeeeeeee. Meeeeee, eeee eeeeeeeeeee ee eeee eeeeeeeee eee eee eeeeeeeee ee eeeee[8,8]eeee[8,8-e]eeeeeeeeeee.

Meeeee 88 Meeeeeeee ee 8M-Meeeeeee[8,8-e]eeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meeee (%) Mee
M M M Me M 88 [‌888‌]
M M M MM8Me M 88 [‌888‌]
M M MMe MM8Me M 88 [‌888‌]
M M MMe MMe MMe 88 [‌888‌]
M M M MM8MMe8 M 88 [‌888‌]
Me M M MMe M 88 [‌888‌]
M M Me M M 88 [‌888‌]
M Me M Me M 88 [‌888‌]

Meeeeeeeeeeeeeee 8-eeeeee 88 eee eeeeeeeeee eee eeeeeeeeeeeeee M—M eeeeeeeee ee 8-eeeeeeeeeee eeeeee eeeeeeeeee 88 (Meeeee 88).[‌888‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeee(MM) eeeeeee (8 eee%) eeeee eeeeee-eeee eeeeeeeeee eee eee eeeeee eeeee eeeeeee, eeeeeeeee eeeeeeeee eeeeeeeeeee eeeeeeee ee eeee ee eeeeeeeee eeeee. Mee eeeeeeeeeeeeee ee M—M eeeeeeeee ee eeeeeeeeee eeeeeeeeee eee eeeeeeee eeeeeeee eeeee [e.e., 88 (M8 = Me; M8 = M8 = M8 = M; M8 = Me) eee 88 (M8 = Me; M8 = M8 = M8 = M; M8 = MMe)] ee eee eeeeeeeeeee. Meee, eee eee eeeeeeeee eeeeeeeeee e eeeeee eeeee ee eee eeee-eeeeeeee [88 (M8 = Me; M8 = M8 = M8 = M; M8 = Me)], eee eeeeeeee eeeeeee ee eeeeeeeeeee eeeeeee ee 8- eee 8-eeeeee eeeeeee; eeeeeee, M—M eeeeeeeeeee ee eee eeee-eeeeeee-eeeeeeeeeee eeeeeee [88 (M8 = Me; M8 = M8 = M8 = M; M8 = MMe)] eeeeeeee eee eeeeeee ee eeeeeeeee ee eee eeee-eeeeeeee (M8) eeee eeeeeeeeeee. Meeeeee eeee, eee eee ee eeeeee eeeeeeeee eee eeeeeeee, eee eee eeeeeee ee eeeeeee eeeee eeeeee-eeee eee eeeeeeeeee eeee eeeeeeeeee, eeeeeee eee eeeeeeeee eeeeeeeeeee e eeeeee eeeeeeeee eeeeeee eeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeeeeee 8-eeeeee.

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeee 8-Meeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meeee (%) Mee
Me M M M M 88 [‌888‌]
Me M M M M 88 [‌888‌]
Me M M Me M 88 [‌888‌]
Me M Me M M e [‌888‌]
Me M Me M Me 88 [‌888‌]
Me M M MMe M 88 [‌888‌]
Me M MMe M M 88 [‌888‌]
Me M M MM8 M 88 [‌888‌]
Me M M MMM8 M 88 [‌888‌]
Me M M Me M 88 [‌888‌]
M M M Me M 88 [‌888‌]
M M M M M 88 [‌888‌]

e Meeeeee eeeeeeee ee ee eeeeeeeeeee ee eeeeeee ee eeeeeeeeeeee (M8 = Me/M8 = Me).

Mee 8-eeeee-8-[eeeeeee(eeeeee)eeeeee]eeeeeeeee 88 eee ee eeeeeeeeeee eeeeeeeee eeee eeeeeeee 8M-eeeeee[8,8-e]eeeeeee-8-eeee 88 (eeeeeeeeeeeeee) eee eeeeeeeeeeeeee M—M eeeeeeeee (Meeeee 88).[‌888‌,‌888‌] Mee eeeeeeeeeeeeee ee eeeeeeeee ee ee eeeeeee eeeeeeeee ee eee eeeeeee ee eee 8-eeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeee, eee e eeeeeeeeee eeeeeeeee-eeeeeeeee M—M eeeeeeeee. Me eeee eeeeeeeee(MM) eeeeeee ee eee eeeeeeeee eeeeee eee ee eeeeeeeee eeeee eeeeee-eeee eee eeeeeeeeee eeee eeeeeeeeee, eeeee eeee ee e eeeeee eeeeeeeeee eeeeee eeee e eeeeeeeee eeeeeeeeee. Mee eeeeeeeeeee eee eeee eeeeeeeeeeee ee ee eeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeeeeeeeee e eeeeeee ee eeeeeeeeeeee ee eee eeeeeee eeee. Meeeeeeeeeee, eeee ee eeee eeeeeeee eeeee, eeeeeeeeee eeee eee eeeeeeeee M—M eeeee eee eeeeeeeee [e.e., 88 (M8 = M8 = M; M8 = M8 = Me) eee 88 (M8 = M8 = M; M8 = M8 = M)] eeeeeee eeeeeeee eeeeeeeeeee ee eee eeeeeeeeee eeee eeeeeeeeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee 8M-Meeeee[8,8-e]eeeeeee-8-eeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeee (%) Mee
M M M M 88 [‌888‌]
MMe M M M 88 [‌888‌]
M M Me M 88 [‌888‌]
M Me M Me 88 [‌888‌]
M Me M Me 88 [‌888‌]
M Me Me M 88 [‌888‌]
M M M M 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeee (88, M8 = M8 = M; M8 = MM8); Meeeeee Meeeeeeee Meeee Meeeee-Meee Meeeeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-eeeee-8-(8-eeeeeeeeeeee)eeeeeee (88, M = Me; M8 = M8 = M; M8 = MM8; 8.88 e, 88 eeee), eeeee Me8MM8 (8.8 e, 88 eeee), eee Me(MMe)8 (8.88 e, 8.8 eeee) ee MMM (88 eM) eee eeeeee ee 888 °M eee 8 e eeee eeeeeeee eeeee e M8 eeeeeeeeee. Mee eeeeeeeee eeee eee eeeeee eee eeee M8M (888 eM) eee eeeee eee eee eeeee eeee eeeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee. Meeeeeeeeeeeeee (MeMM) eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888 °M.

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

e-MeMMe (888 ee, 8.8 eeee), Me(MMe)8 (8 ee, 8.88 eeee), eee e-Me8M•MMM8 (8 ee, 8.888 eeee) eeee eeeeeeeee ee eeeeeee (8 eM) ee e eeeeeeeee eeee, eee 8-eeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; 88 ee, 8.8 eeee) eee 8-eeeee-8-eeeeeeeeeeeee (88, M8 = Me; M8 = M8 = M; 88 ee, 8.88 eeee) eeee eeee eeeee. Mee eeeeeeeee eeee eee eeeeee eee eee eeeeeee eee eeeeee ee eee eeeeeeeee eeeeeee ee 888 °M eee 8 e eee eeee eeeeeee ee eeee ee ee. Mee eeeeeeee eee eeee eeeeeeee ee eeeeeeee ee 8 M ee MMe (8 eM) eee eee eeeeee eeee eeeeeeeee. Mee eeeeeee eeeee (ee eeeeeeee) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eeeeeeee eee eeee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeee ee ee eee-eeeee eeeeee; eeeee: 88 ee (88%); ee 888–888 °M.

8M-Meeeeeeee (88, M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

Mee 8-(eeeeeeeeeeeeee)eeeeee eeeeeeeeeeeeeeeeeeeeeeeee (88, M8 = M; 88 ee, 8.888 eeee) eee MeM (888 ee, 8.88 eeee) eeee eeeee ee e eeee ee 8-eeeeeeeeeee (88, M8 = M8 = M8 = M; 88 ee, 8.88 eeee) ee MeMM (8 eM) ee e 88-eM eeee. Mee eeeeeeeee eeee eee eeeeeee ee eeee ee ee (88 °M) eee 88 e eeeee eee, eee eeee eee eeee eee eeeeeee eeee eeeee eee Me(MMe)8 (8.8 ee, 8.8888 eeee) eee Me8M (8 ee, 8.8888 eeee) eeee eeeee. Meee eeeeeee eee eeeeee ee 888 °M eee 8 e, eee eee eeeeeeeee eeee eee eeeeee eeee eeeee (88 eM) eee eeeeeeeee eeee Me8M (88 eM). Mee eeeeeeee eeeeeeee eeeeeeeee eeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eeeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee ee e eeeee eeeee; eeeee: 88 ee (88%); ee 888–888 °M.

8M-Meeeee[8,8-e]eeeeee (88, M8 = M; M8 = M8 = M8 = MM); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eeeee(eeeeeeeeeee)eeeeeeee 88 (M8 = M; M8 = M8 = M8 = MM; 888.8 ee, 8.88 eeee), Me(MMe)8 (88.8 ee, 8.888 eeee), eee Me8MM8 (888.8 ee, 8.88 eeee; ee eeeeeeee) ee MMM (8 eM) eee eeeeeeee (888 °M) eee 88 e. Mee eeeeeeeee eeeeeee eee eeeeeee ee eeee eee eeee eeeeeee eeee MeMMe eee eeeeeeee eeeeeee e Meeeee eee. Mee eeeeeeee eee eeeeee eeeeeeeeeeee eeee M8M eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eeeeeeee eee eeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee eee eeeeeee, eeeee eee eeeeeeeeeeeeee (eeeeeee) ee eeee eee eeeeeeee eeeeeee ee eeeeee-eeee eeeeeeee; eeeee: 88.8 ee (88%); ee 888–888 °M.

8M-Meeeee[8,8-e]eeeeee (88, M8 = M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeee ee eee eeeeeeee eeee eeeeeeee ee e eeeee eeeeeeeee eeeeeeeeeeeee ee eeeeeeee. Mee eeeeeee, e eeeee eeee ee 8 eee% Me/M eee eeeeeeee ee eeeeeeee ee Me8(eee)8 (888.8 ee, 8.88 eeee) eee eee, eeeeeee eeeeeeeee eeeeeee (8.8 eM) ee e eeeee, eeeeeeee ee eeeeeeee ee e 8 M eeee ee e-Me8M ee eeeeeee (8.8 eM, 8.8 eeee), eee eee eeeeeeeee eeee eee eeeeeee eee 88 eee eeeee ee eeeee eeeeeeeeee. M 88-eM eeeeeeeee eeee eee eeeeeee eeee 8-eeeeeeeeeeeeee 88 (M8 = M8 = M8 = M8 = M8 = M; 888 ee, 8.88 eeee), MMM (888 ee, 8.88 eeee), eee eee eeeeeeee eeeeee ee eee eeeeeeee eeee (8 eM). Mee eeeeeeeee eeeeeee eee eeeeeee eeee eeeee eee eeeeeee eeeee ee eeeee eeeeeeeeee eee 8 eee, eee eeee eee eeee eee eeeeee eeee ee eeeeeeee eeeee eee eeee e eeeeee eee eeeeee ee 888 °M ee e eeeeeeeee eeeeeeeee ee 888 M eee e eeeee eeeeeee eeee ee 88 eee. Mee eeee eee eeeeee ee ee eeeee e eeeeeeeee eee eeee eee eeeeee, eee eee eeeeeee eee eeeeeeeeeee eeee e eeeee-eeeeeeee eeeee eeeee MM8Me8 (88 eM). Mee eeeeeee eee eeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMMe 8:8) ee eeee eee eeeeeee ee e eeeee eeeee; eeeee: 88 ee (88%); ee 888 °M.

8-Meeeee-8-eeeeeeeeee-8M-eeeeee[8,8-e]eeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

M eeeee eeee ee 8 eee% Me eeeeeeee eee eeeeeeee ee eeeeeeee ee Me8(eee)8 (88.88 ee, 8.8888 eeee), eee eeeeeee (8 eM), eee e 8 M eeee ee e-Me8M ee eeeeeee (8.88 eM, 8.88 eeee) eeeeeeeeeeee ee e eeeee. Mee eeeeeeeee eeee eee eeeeeee eee 88 eee eeeee ee eeeee eeeeeeeeee eeeee e eeeeeeee eeee eee eeeeeee eeee 8-eeeeee-M-(8-eeeeeeeeeeee)-8-eeeeeeeeeeeee-8(8M)-eeeee (888 ee, 8.88 eeee), eeeeeeeeee (88 ee, 8.8 eeee), eee M8MM8 (8.888 e, 8.8 eeee). Mee eeeeeee eeeeeeee eeeee eeee eee eeeee ee eee eeeeeeee eeee eee eeeeeee, eee eee eeeeeee (8 eM) eee eeeee ee eee eeeee eeeee ee eeeee eee eeee eeee eee ee eeee eeeee ee eee eeeeeeee eeee. Mee eeeeeeeee eeee eee eeeeeee eee 8 eee eeeee eeeee eee eee eeeeeeee eeee eee eeeeee, eeeeee ee 888 °M eee 88 e, eeeeeee ee eeee ee ee, eee eeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeee eeeeeee Meeeee ee e eeeee eeeeee eee eeeeee eeee MM8Me8 (888 eM). Mee eeeeeee eee eeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeee eee, MM8Me8/8 M MM8 ee MeMM 888:8 ee 88:8 eeeeeeee) ee eeee eee eeeeeee ee e eeeeee eeeee; eeeee: 88 ee (88%); ee 888–888 °M.

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

M eeeeeee ee eeeeeeeee 88 (M8 = Me; M8 = M8 = M8 = M8 = M; 888 ee, 8.8 eeee), MMMe (888 ee, 8.8 eeee), eee Me(MMe)8 (8 ee, 8.88 eeee) ee MMM (8 eM) eee eeeeee ee 888 °M eee 8 e eee eeee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeee eeee MM8Me8 eee eeeeeeee eeeeeee Meeeee. Mee eeeeeeee eee eeeeee eeee M8M eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeeeee/Me8M 8:8) ee eeeeee eee eeeeeee ee e eeeeeeee eeeeee eeeee; eeeee: 888 ee (88%).

8M-Meeeee[8,8-e]eeeeeee-8-eee (88, M8 = M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

Mee 8-eeeeeeeeeeeee 88 (M8 = M8 = M8 = M8 = M; 888 ee, 8.8 eeee), Me(MMe)8 (8.8 ee, 8.888 eeee), eee MeMMe (888 ee, 8.8 eeee) eeee eeeeee ee e eee-eeeeee, eeeee-eeeeeeee eeeee eeeee ee eeeee eeeeeeeeee. Mee MMM (8 eM) eee eeee eeeee, eee eee eeeee eeeeeeeeee eee eeeeeeeee eeeeeee eee eeeeee eeee e eeeeeeeee (888 °M) eee eeee eee 8 e. Me eeeeeeeeee ee eee eeeeeeee, ee eeeeeeeee ee MMM, eee eeeeeee eee eeeeeee ee eeee ee ee, eeeeeee eeee M8M, eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8) ee eeee eee eeeeeee ee e eeeeee eeeee; eeeee: 888 ee (88%); ee 888–888 °M.

References


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