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Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 89.
The most common methods for the synthesis of α-(o-aminoaryl) ketones are: (1) the acylation of enamines or arenes (Friedel–Crafts) with (o-nitroaryl)acetyl chlorides and (2) the ortho nitration of α-aryl ketones, followed in each case by nitro group reduction; these types of process are covered in other categories of Science of Synthesis. Given in the rest of this section are the most important routes to α-(o-aminoaryl) ketones, which have been targeted for the eventual construction of indoles. It is relevant to repeat that once produced, and especially under acid catalysis, α-(o-aminoaryl) ketones readily undergo ring closure with loss of water to generate the aromatic pyrrole ring.
Mee eeeee eeeeeeee 888 eeeeeeeee eeee eeeeeeeeeeee ee 8-eeeeee-8-eeeeeeeeeee 888 eee eeeeeeee eeeeeeeee eee eeeeeeee ee eeeeeee eee eeeee eeee eeeeeee ee eeeeeee eeeeeeeee eeeee eeeee eeeeeeeee.[888] Me eeeeeeeeeee ee ee eeeeee eee eeeee eeeee eeeee ee eeee 888, eeee eeeeeee 888 eeee 8-eeeeeeeeeee 888 ee eeeeeeeee eeeeeeeee ee eee eeeeeee, eeeeeeee ee eeeee-eeeeeeeee eeeeeeeeeeeeeee-eeeeeeeeeeeeeee ee eeeee eeeee eeeeeeeeee eeeee e eeeeeeeee ee eeeeeeeee eeeeeeee; eee eeeee eeeeeeeee eee ee eeeeeeeee ee eeeeeeee eeee eeeee eeeeeeeeeeeee ee eeeeee ee eeee ee eeeeeeee eeee eeeee eeeeee eeeeeeeee eee eee eeeeeeee (Meeeee 888).[888]
Meeeee 888 8-Meeeee-8M-eeeeeee eeee 8-Meeeee-8-eeeeeeeeeee eee Meeeeeeeeeee[888]
Meeeeeeeeeee ee eeeeeeeeeeee eeee 8-eeeeee-M-(eeeeeeeeeeeeee)eeeeeee (888), eeeee eeeeeeeeeeee ee eeee, eeeee eeeeeeee ee e 8-(e-eeeeeeeee)eeeeeee (888), eeeeeeeee eeee eeeeee 8-eeeeee-8M-eeeeee (88) (Meeeee 888).[888]
Meeeee 888 8-Meeeee-8M-eeeeee eee Meeeeeeeee ee 8-Meeeee-M-(eeeeeeeeeeeeee)eeeeeee[888]
Mee eeeee-eeeeeeeee eeeeeeeeeeee ee eeeeeeee eeeeeee ee eeeeee eeee 8-eeeee- ee 8-eeeeeeeeeee 888 eeee eeeeeeee ee eeeeeee 888 ee e eeeeee eeeeee, eeeeee eeeeeeeeeee eeeeeeee eeeeeeeeeeee, eeeee ee α-(e-eeeeeeeee) eeeeeee 888, eeeee eeeeeee ee 888 ee eee eeeeee eeeeeee eeeeeeee eeeeee (Meeeee 888).[888–888] M eeee eeee eeeeeeeeee eeeeeee ee eee ee eeeee eeeeeeeee ee eeeeeeee eeeeeeeee.[888]
Meeeee 888 Meeeeee eee Meeeeeeeeeeee MMM8 Meeeeeeee[888–888]
Mee eeeeee ee 8-eeeeeeeeeee eee ee eeeeeeeee ee eeeeeeee ee 8,8-eeeeeeeeee eeeeeeeee eeeee eeeeee(M) eeeeeeeee, eeee eeeeee eeee, eee 888, ee eeeeeee 888 eeee e 8-eeeeeeeeeee ee 8-eeee eeeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeee eee Meeeee-Meeeeeeee Meeeeeeeeeee ee Meeeee eeee e-Meeeeeeeeeeeee[888]
Me eeeeee eeeeeeeeeeee eeeeeeeeeeee, eeeeeee eee eeee eee eeeee eeeeeeeee, ee eeeeeeee eeeee 8-eeeeeeeeeeeeeee 888, eee eeeee eeeee eeeee eeeeeee ee eeeee ee e eeeee eeeee: Meeeee 888 eeeee eeee eeeeeee ee eeeeee eee eee eeeeeeeee ee 8-eeee-8M-eeeeee-8-eeeeeeeeee eeeee 888.[888]
Meeeee 888 Meeee 8-Meeeeeeeeeeeeeeee eee Meeeeeeeeeee Meeeeeeeeeee eeee 8,8-Mee Meeeee[888]
| M8 | Meeee (%) | Mee |
|---|---|---|
| 8-eeeeeee | 88 | [888] |
| Me | 88 | [888] |
| 8-eeeeeee | 88 | [888] |
| e-Me | 88 | [888] |
Meeeeeeee eeeeeeeee eeee eeeee eeeee eee eeeeeeeeeee ee 8-eeeeeeeeeeeeeeee (ee 8-eeeeeeeeeeeeeeeee) eeee 8-eeee eeeeee, e.e. 888, ee eeee 8-(8-eeeeeeeeeee)eeeeee, e.e. 888; eeeeeeeee ee eeeee eeeeeeee eeee eeeeeeee 8M-eeeeeee, e.e. 888,[888,888] ee eeeee ee eee eeeeeee ee Meeeee 888. Meee, eeee 8-(8-eeeeeeeee)eeeeee eee eeee eeeeeeeeeeeee ee ee eeeeeeeeeee eeeee, eeeeeeeee ee eeee eeee 8-eeee-8M-eeeeeee (Meeeeee 88.88.8.8.8.8.8.8, Meeeee 888).
Meeeee 888 8M-Meeeeee eeee 8-Meee Meeeee eee 8-Meeeeeeeeeeeeee[888]
Me eee eeee eeeee eeee M,M-eeeeeeee-8-(e-eeeeeeeee)eeeeeeeeeee (Meeeeeeeee–Meeeee eeeeeee eeeeeeeeeeeee, eee Meeeeee 88.88.8.8.8.8.8.8.8) eee ee eeeeeeee; eeee eeeeeeee ee eeee eeeeeeee ee ee eeeeeee ee eeeee eeeee ee eeeeeeeeee (e.e., 888 ee 888);[888] eeeee ee eeeee eeeeeeee eeeeee eeeeeeeeeeee ee ee eeee eeeeee (e.e., 888 ee 888).[888] Me eee eeeeee eeeeeeee (Meeeee 888), eeeeeeeee ee eee eeeee eeeee eee eeeeeeeeeee eeeeeeee e 8-eeeeeeeeeee 888. Me eee eeeeee eeeeeeee, eee eee-eeeeee eeeeeee ee eeeeeee eeeeeeeeeeeeee eeee 888; eeeeeeeee ee eee eeeee eeeee ee 888 eeeee ee e 8-eeeeeeeeeee eeeeee 888 ee eeeee ee Meeeee 888.
Meeeee 888 Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeeeeeee eee M-Meeeeeeeeeeeeeeeeeee ee ee M,M-Meeeeee-8-(e-eeeeeeeee)eeeeeeeeee[888]
Meeeee 888 8-(8-Meeeeeeeeeee)-8M-eeeeee eee M-Meeeeeeee ee ee M,M-Meeeeee-8-(e-eeeeeeeee)eeeeeeeeee[888]
Meeeeeeeee–Meeeee eeeeeee 888 ee eeeeeeee eeee eeee eeeeeeee 888 ee eeee eeeeeee 888. Meeeeeeeee ee eee eeeeeee eeeeeeee ee eeeeeeeeee ee eee eeeeeeee eeeeeeeee eeeee ee 888 eeeee eeeeee 888, eeeee ee eeeeeeeee ee eee eeeee eeeee eeeeee ee eeeeeee e 8,8-eeeeeeeeeeeee 888, ee eeeee ee Meeeee 888.[888]
Meeeee 888 M 8,8-Meeeeeeeeeeee Meeeee eee Meeeeeeeee ee ee α-(e-Meeeeeeee) Meeeee[888]
Mee eeeeeeeee ee eeeeeee eeeeeeee,[888] eeeeee eeeeeeeeeeee (Meeeee 888),[888] ee Meeeeee’e eeee[888] eeeeee eeee e-eeeeeeeeeeeeeee eeeeeeeee, e.e. 888, eeeee α-(e-eeeeeeeee) eeeeeee eeee ee 888 eeeeeeeee 8,8-eeeeeeeeee eeeeeee Meeeeee eeeeeeee. Meeeeee eeeeeeeee eeeeeeeeee eeeee ee ee eeeeee, eeeeee 8-eeeeeee-8M-eeeeee-8-eeeeeee (888) ee eeee eeee, ee eee eeeee eee.
Meeeee 888 Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeee eee Meeeeeeee ee e 8,8-Meeeeeeeee Meeeeeee eeee ee e-Meeeeeeeeeeeeee Meeeeeee[888]
Meeeeee eeeeeeeeeee eeeee ee α-(e-eeeeeeeee) eeeeeee eeeeeeee eeeeee eee eeeeeeeeeeee eeeeeeeeeeee ee eeeeeee eeeee ee eeeee ee ee eeeee eeee e eeeeeeeee, e.e. eee eeeee ee eeeee eeeeeeeeeeee[888] ee ee eeeeeeeeeeeee eeeeee 888 eeee 888 eee eeeeee 8,8-eeeeeeee-8M-eeeeee (888) (Meeeee 888).[888]
Meeeee 888 8,8-Meeeeeee-8M-eeeeee eee Meeeeeeee Meeeeeeeeeee ee Meeeee ee e 8-Meee-8-eeeeeeeeee[888]
Meeeeeee eeeee eeeeeeeee eee ee eeee ee eeeeeeee[888] eeee eeeee eeee eeeeee eeeee eeee(eeeeeeeeeeeee)eeeeee (eeeeeeeeeeeeee)eeeeeeeeee (MMMM); Meeeee 888 eeeee eee eeeeeeee eee-eeeeeeee eeeeeeeeeeee eeeeeeeee 888 eeee eeeeeeeeeee ee 8-eeeeee-8-eeeeeeeeeeee (888) eeee 8-(eeeeeeeeeeeeeee)eeeeeeeeeee (888) eeeee eeeeeeee ee eeeeeee eeeeeeeee, ee eeeeeee e 8-(e-eeeeeeeee)eeeeeeeeeeeee 888 eee eeeeee 8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee (888).[888]
Meeeee 888 8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee eee e Meeeeeeeee/Meeee Meee Meeee Meeeeeeeeeee[888]
Me e eeeee eeeeeeeee eeeeeeeeeeee eeeeeeee, eee eeeeeeee ee 8,8-eeeeeeeeee eeeeeee eeee eee ee eeeee-8,8-eeeeeee eeeeeee eeeeeeeeeeee (888) ee eeeeeeeeeeeee, eeeeeeeeee α-(e-eeeeeeeee) eeeeeee, e.e. 888, eeee eeeeeee, eeee 8,8-eeeeeeeeee eeeeeeee, eeee eeeeee 8M-eeeee-8-eeeeee, eeee ee 8-eeeeee-8M-eeeee-8-eeeee (888) (Meeeee 888).[888]
Meeeee 888 8-Meeeee-8M-eeeee-8-eeeee eeee Meeee-8,8-eeeeeee Meeeeee Mee(eeeeeeeee)[888]
Mee eeeeeeee ee e-eeeeeeeeeeeeeeeeeee eeeee eeee eeee eeeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeeee eeeeeeee 8-eeeeeee-8-eeeeee-8-(e-eeeeeeeee)eeeeeee [e.e., 888 eeeeeee eeee 8-eeeeeeeeeeee (888)], eeeee eee ee eeeeeee ee eeee 8M-eeeeee (8) eeeeee ee eeee eeeeeeee (Meeeee 888).[888] Me e eeeeeeeeee eee, eee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeee eeeeeeee 8-eeeee-8-eeeeee-8-[(e-eeeeeeeee)eeeeeeeee]eeeeeee, eeeee eeee eeeeeee eeeee eeeee eeeee eeeeeeeee.[888] 8-Meeeeeeeeeeeeeeeeeeee eeeeeeee eeeeee eeee eeee-8,8-eeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeeee eeeeee 8-eeeeee-8-(8-eeeeeeeeeee)eee-8-eee eeeee, ee eeeeeeeeee eeeeeeee ee eee eeeeee eeee (ee. Meeeeee 88.88.8.8.8.8.8.8.8) eee eeeeeeeee ee eee eeeee eeeee, eeeeeeee 8M-eeeeee eeeeee.[888] Meeeeeeeeeeee, e-eeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeee eee ee eeeeee eeeeeeee ee eeeeeeeeee ee eeeeeeee.[888]
Meeeee 888 8M-Meeeee eee Meeeeeee Meeeeeeee ee ee Meee Meeee[888]
Mee eeeeeeee ee M-eeee-M-eeeeeeeeeeeeeeeeee 888 eeee eeeeeeee (888) eeeeeeee eeeeeee 888 eeeee eeeeeeeee ee eeeeeee ee eeeeeee ee α-(e-eeeeeeeeeeeee) eeeeeee 888 (Meeeee 888).[888]
Meeeee 888 α-(e-Meeeeeeeeeeee) Meeeeee eeee M-Meeeee-M-eeeeeeeeeeeeeeeeee eee Meeeeeee[888]
Mee ee eee eeee eeeeeeeee eeee ee eeeeee ee e 8-(e-eeeeeeeee) eeeeee eeeeeeeeee eeeee ee eee eeeeeee ee e eeeee ee eeeee ee e eeeeeee eee e 8,8-eeeeeeeeee eeeeeeee. Me eeeeeee ee eeee eeeeee ee eeeee ee Meeeee 888.[888] Meee, eee eeeeeeee eeeeeee 888 eeeeeeeee ee eeeeeeeeeeee ee eeee eeeeeeeee, eeeee eeeeeee eeeeeeeeeeeee eeeeeeeeeee ee eee eeeee 8-eeeeeeee, eeee eeeeeeeee eeeeeeeeeeee 888. Meeeeeeee ee eeee eeee eeee eeeee e 8M-eeeeee 888, eeeeeeee eee e eeeee-eeeeeeeeee eeeeeee 888.
Meeeee 888 Mee ee e Meeee ee e Meeeeee eee e 8,8-Meeeeeee[888]
| M8 | Meeee (%) ee 888 | Meeee (%) ee 888 | Mee |
|---|---|---|---|
| Me | 88 | 88 | [888] |
| e-Me | 88 | 88 | [888] |
| 8-Mee | 88 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meeee-8-eeeeee-8M-eeeeee (888, M8 = M; M8 = Me); Meeeeee Meeeeeeee:[888]
Meeee M8, e eeeeeee ee 8-(8-eeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeeee (8.88 e, 88 eeee), eeeee eeeeeeee (8.8 e, 88 eeee), eee eeeee Me8M (88 eM) eee eeeee ee eeeee eeeeeeeeeeeee (8.8 e, 88 eeee) eeeeeeee ee 8°M. Meeee eeeeeeee eee 8 e ee ee, eee MMe eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeee eeeee 8-(8-eeeee-8-eeeeeeeeeee)-8-eeeeeeeeeee eeeeeeeee eeeee eeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)/Me8M 88:8]; eeeee: 8.88 e (88%); ee 888–888°M.
Meeee 8-(8-eeeee-8-eeeeeeeeeee)eeeee eeeeeeeee (8.8 e, 8 eeee) eee Me(MMe)8 (8.888 e, 8.8 eeee) eeee eeeeee ee eeeeeeeee eeeeeee (88 eM) eeeee M8 eee 88 e. Mee eeeeeee eee eeeeee eee eeeeeeee, eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/eeeeeee 8:8) ee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-Meeeee-8M-eeeeee (88); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeee(MM) eeeee eeee eeeeeeeee eee eeeeeeeeeee eeeeee eee ee eeeeeeeeee ee e eeeee eeeeeeeeee.
8.8 M MeMe (8.8 eM, 8.88 eeee) eee eeeee eeeeeeee eeee 8 eee ee 8-eeeeee-M-(eeeeeeeeeeeeee)eeeeeee (888; 8.88 e, 8.88 eeee) ee eeeeeee (8 eM) ee 8°M. Mee eeee eeeeee eeee eee eeeeeeee eee 88 e, eeeeee ee -88°M, eee eeeeeee eeee MMM (8 eM). Meeeeeeeeeee (8.88 e, 8.88 eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee. Meeee eee Me8M eeee eeeee eee eee eeeeeeeee eeeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee eee eee eeeeeee eee eeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee 8-(8-eeeeeeeeeee)-8-eeeeeeeeeeeee (888); eeeee: 8.88 e (88%); ee 88–88°M.
8-(8-Meeeeeeeeee)-8-eeeeeeeeeeeee (888; 88 ee, 8.888 eeee) eeeeeeeee ee eeeeeeee (8 eM) eeee eeee M8M (888 μM) eee eeeeeeee ee eee eeeeeeee ee MeM8 (88 ee). Mee eeeeeee eee eeee eeeeeee ee ee eee 8 e. Meeeeeee eeee Me8M, eeeeeeeeee eeeeeee Meeeee, eee eeee eeeeeeeeeeeee ee eee eeeeeeee eeee e eeee eeeee eee eeeeee eeee M8M, eeeee (MeMM8), eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee eee eeeeeee; eeeee: 8 ee (88%); ee 888–888°M.
8-Meeeee-8M-eeeeee-8-eeeeeeeeee Meee (888); Meeeeee Meeeeeeee:[888]
Meeeeee eeeee M8, ee MMM8 (88 eeee) ee eeeeee MM8 (888 eM) eeee eeeee eeeeeeeeeeee, eeeeeee (8.88 e, 88 eeee), e-MeMM (8.888 e, 8 eeee), e-MeMM (8.88 e, 88 eeee), eee eeee 8-eeeee-8-eeeeeeeeeeeee eeee (8.88 e, 88 eeee). Mee eeeeeee eee eeeeeeeeee eeee MM eeeee eeee eeeeeee eeeeeeee ee 888 ee eee 88 e. MM8MM8 (8.8 e, 88 eeee) eee Me8M (8 eM) eeee eeeee eee eee MM8 eee eeeeeee ee eeeeeeeee eeeeeeeee. Mee eeeeeee eee eeeeee ee ee eee eeeeee eee ee eeee eee eeeeeee; eeeee: 8.88 e (88%).
Meeee 8-Meeeee-8M-eeeeee-8-eeeeeeeeeee (888, M8 = Me; M8 = MMe); Meeeeee Meeeeeeee:[888]
MeM (88% ee eee, 8.88 e, 8 eeee) eee eeeeee eeee eeee eee eee eeeee M8, eee eeee MMM (8 eM) eee eeeee 8-eeeeeeeeeeee (8.888 e, 8.8 eeee) eeee eeeee eeeeeeee eeee eeeeeeee. Meeee eeeeeeee eeeeeeeee eeeeee, MeM (8.888 e, 8.8 eeee) eee eeeee eeeeeeeeee eee eeee eeee eeeeee eeee eeeeee, eee eeee 8-eeeeeeeeeee (8.888 e, 8 eeee) eee eeeee. Mee eeeeeee eee eeeeee ee 888°M eee 8 e, eeeeee, eee eeeee ee M8M (88 eM), eee eee eeee eee eeeeeee ee eM 8–8. Me8M (8 × 88 eM) eee eeee ee eeeeeee eee eeeeeee. Mee eeeeeeee eeeeeee eee eeeeee eeee M8M (8 × 88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)/eeeeee] eeeeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeee ee e eeeeee eeeeeeeeeee eeeeeeee eee eeee eeeee ee eeeeeeeeee.
M 8.88 M eeee ee MMMe8 ee eeeeeee (8.8 eM, 88.8 eeee) eee eeeee ee 8-[8-(8-eeeeeee-8-eeeeeeeeeee)eeeee]eeeeeeeeeee (888; 8.88 e, 88 eeee) eee Me8M (8 eM) ee eeeee eeeeeee (88 eM) ee -88°M. Meeee 88 eee, eee eeeeeee eee eeeeeee ee ee eee eeeee 8 e, eeeeeeee ee -88°M ee eeeee eeeee Me8M (8.8 e, 88 eeee) eee MeMM (8 eM) eeee eeeee. Meeee 8 e ee ee, eee eeeeeee eee eeeeeee eeee eeeeeee (88 eM) eee eee eeee eee eeeeee eeee M8M (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee (eeeeee eee, eeeeee/MeMMe) eeee eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeeee (888); eeeee: 8.88 e (88%); ee 888–888°M.
M eeeeeeeeee ee eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeeee (888; 8.88 e, 8 eeee) eee Me/M (88%, 8.88 e) ee MeMM (88 eM) eee MeMMe (8 eM) eeee MeMM (8.8 eM) eee eeeeeeeeeeee ee 8.8 eee ee ee eeeeeeeee. Mee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeee eeeeeee Meeeee eee eeeeeeeeeeee. Meeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-(8-Meeeeeeeeeee)-8M-eeeeee (888); Meeeeee Meeeeeeee:[888]
M eeee ee M,M-eeeeeeee-8-(8-eeeeeeeeeee)eeeeeeeeee (888; 88.8 e, 8.888 eee) eee Me8M (88.8 e, 8.888 eee) ee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eeeee eeeeeeee ee 8-eeeeeeeeeeeee eeeeeeee (88.8 e, 8.888 eee). Mee eeeeeee eee eeeeeee ee eeeeee eee 88 e eee eeee eeeeee, eee eeeeeeeeee M8M eee eeeee ee eeeeeeee eee eeeeeeeeeeee eeeee. Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeeeeee ee eeee ee eee, eeeee eee eeeeeeeee ee 8,8-eeeeeee (88 eM) eee M8M (88 eM) eee eeeeee ee eeeeee eee 88 e. Mee eeeeeee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eee eeeee eee eeeeeeeeeeee ee eeee ee eee, eeeee eeee 8-(8-eeeeeeeeeeee)-8-(8-eeeeeeeeeee)eeeeeeee (888) ee eeeeeeeeeeeeeee (eeee MeMM); eeeee: 88 e (88%); ee 88–88°M.
8-(8-Meeeeeeeeeee)-8-(8-eeeeeeeeeee)eeeeeeee (888; 88.8 e, 8.88 eee) ee MMM (888 eM), MeMM (888 eM), eee M8M (888 eM) eee eeeeeee ee eee eeeeeeeeeee eeeeeeee ee Me8M8M8 (88 e). Mee eeeeeee eee eeee eeeeeee eee eeeeee ee 88°M eee 88 eee. M8M (888 eM) eee eeeee eee eeeee 88 eee ee ee, eeeeeee Me8M8M8 (88 e) eee eeeee eee eee eeeeeee eee eeee ee ee eee 88 eee. Meeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeeeee eeeeeeee eee eeeeeeee ee eeeeeeeeee ee eee eeeeeeeee eeeee, eeeee eee eeeeee eeee M8M. Mee eeeeeeee eee eeeeeee eeee 8 M MMe (888 eM) eee eeeeee ee 88°M eee 88 eee, eeeeeeeee, ee eeeeeee, eeeeeee eeeee eeeeeeee eee eeeeeeee eee eee eeeeeeeee ee eeeeeeeeee. Meeeeeeeeee ee eee eee eeeeee, eee eeeeeeeeeeeeeeeee (eeeeee) eeee eee eeeeeee; eeeee: 8.8 e (88%); ee 88–88°M.
Meeeee 8-Meeeeee-8M-eeeeee-8-eeeeeee (888); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeee eeeeeeee eee eeeee eeeeeeeeeee eeee eeeeeee eee ee ee eeeeeeee.
M eeeeeeeeee ee (8-eeeeeee-8-eeeeeeeeeee)eeeeee eeee (88.8 e, 8.888 eee) eee MMMe8 (8.8 eM) ee eee MMM (888 eM) eee eee eeeeeee eee eeeeeee ee ee eeeeeeeee eee eeee eeeeee ee 88°M eeeeee e eeeee eeee ee eee eeee eeeeeeee 888. M eeee ee eeeeee eeeeeeeeeeee (88.8 eM, 8.8 eee) ee MMM (88 eM) eee eeeee eeeeeeee ee e eeeeeee eeee (8–8°M) eeeeeeeeee ee MeM ee MMM. Mee eeeeeeeee eeeeeee eee eeeee ee e eeeeee eeee ee 888 eee eee eeeeeee eee eeeeeee eeeeeeeee. M8M eee eeeee eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 888 eM) eee eee eeeeeeee eeeeeee eeeee eee eeeeee eeee M8M eee eeeee (Me8MM8). Mee eeeeeeee eeeeeee eeeee eee eeeeeeeeeeee ee eeeeeee eee eee eeeeeee eee eeeeeeeee ee Me8M/MeMM (8:8) eee, ee eeeeeee ee -88°M eeeeeeeee, eeeeeeee ee eeeeee [(8-eeeeeee-8-eeeeeeeeeee)eeeeee]eeeeeeeeeeee eeeeeeeee eee eeee eeeeeeeee eee eeee eeee ee eeee eee eee eeee eeee; eeeee: 88.8 e (88%).
Me MM8 (88 eM) eee eeeee ee e eeeeeeeeee ee eee eee eeeee (8.88 eee) ee MeMM (888 eM). Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 eee. Mee eeeee eeeee eee eeeeeeeee; eeeee: 8.8 e. Meeeeeeeeeeee ee eee eeeeeeee eeee ee eeeeeeeeee eeeeeeee (8.88 e) eee e eeeeeeee eeeee ee eeeeee 8-(8-eeeeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeee (888) ee 8.88 e (88%), eeeee eee eeee ee eee eeee eeee.
Me e eeeeeeeeee ee eee eeeee (8.8 e, 8.888 eee) ee eee MeMM (888 eM) eee eeeee Me/M (88%, 888 ee) eeeeeeee ee MMM8MM8 (88.8 e, 8.888 eee). Meeee eeeeeeee ee ee, eee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eee eeeeeeee eee eeeeeeeeeeee ee eeeeeee ee eeeee e eeeeeee, eeeee eee eeeeeeeeee eeee M8M, eeeeeeee, eee eeeee eeeeee eee eeeee eeeeeee; eeeee: 8.88 e (88%), ee 88–88°M (MeMM).
M eeeeeee eeeeeeeee eee eeee eeeeeeee eee ee eeeee ee eee[888].
8,8-Meeeeeee-8M-eeeeee (888); Meeeeee Meeeeeeee:[888]
8,8-Meeeeeeeeeeeeeee (88.8 e, 8.8 eee) eee eeeeeeee MMM (88 e, 8.88 eee) eeee eeeeeeeee ee MMMM ee eeeeeeee eee 88 eee, eee eeee e eeee ee 8-eeeeee-8-eeeeeeeeeeee (888; 88.8 e, 8.8 eee) ee MMMM (8 eM) eee eeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeee ee 88°M eee 8 e, eee eeee eeeeee eeee M8M eee 8-(8-eeeeeeeeeee)-8,8-eeeeeeeeeeeeeeee (888) eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88.8 e (88%); ee 888–888°M.
8-(8-Meeeeeeeeee)-8,8-eeeeeeeeeeeeeeee (888; 8 e, 8 eeee) ee eeee MeMM (88 eM) eee eeeeeee ee eeeeee Me eeeeee (8 e, 888 eeee) eeeeee eeeeeeeee eee 8 e. M8M (888 eM) eee eeeee eee eee eeeeeeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeee, eee eeeeeeee, eee eee eeeeeee eee eeeeeeeee eeee eeeeeeeee eeeeeee (MMMMMMM: eeeeeeeeee). Mee eeeeeee eeeeeeeeeeee eeeee eeeeee eeeeeeeee eeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee (888); Meeeeee Meeeeeeee:[888,888]
MMMMMMM: Meeeeee ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeeee, eee eeee. Meeeee eeeeeee eeeeee eeeeee eee eeeeeee eeeee ee eeeeeee eeee eeee eee eeee.
8-(Meeeeeeeeeeeeee)eeeeeeeeeee (888; 8 eM, 8.88 eeee) eee 8-eeeeee-8-eeeeeeeeeeee (888; 8.88 e, 8 eeee) eeee eeeeeeeee ee MMM (88 eM) eee eeeeeee eeee MMMM (8.888 e, 8 eeee) eeeeeeeee ee MMM/MeMM (8:8; 8 eM) eeeeeeee eeee 88 eee ee -88°M. Mee eeeeeee eee eeee eeeeeeeee ee -88°M, eeee Me8 (8.88 eM, 8 eeee) eee eeeee eeeeeeee ee eeee eeeeeeeeeee, eee eee eeeee eee eeeeeee ee eeee ee ee. Me8M (8.8 e, 88 eeee) eee eeeee eee, eeeee 8 e ee ee, ee MeMMM8 eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeeeee eee eeeee eee eeeeeeeeeeee ee eeee 8-(8-eeeeee-8-eeeeeeeeeee)eeeeeeeeeeeee (888), eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8.888 e (88%).
8-(8-Meeeee-8-eeeeeeeeeee)eeeeeeeeeeeee (888; 8 e, 8.8 eeee) eee eeeeeee eeee Me eeeeee (8.88 e, 88 eeee) eee MeMM (8.88 e) eeeeeeee eeee MeMMe (8.88 e) ee eeeeeeeee MeMM/M8M (8:8; 88 eM) eee 8 e. Mee eeeeeee eee eeeeee eee eeeeeeeeeeee eee MM8Me8 eee eeee ee eeeeeee eee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee [eeeeee eee, MMe8 (MMMMMMM: eeeee)/MM8Me8 8:8]; eeeee: 8.88 e (88%); ee 888°M.
8-Meeeee-8M-eeeee-8-eeeee (888); Meeeeee Meeeeeeee:[888]
M,M′-(Meeeeeeee-8,8-eeeee-8,8-eeeeeeeee)eee(eeeeeeeee) (888) eeeeeeeee ee eee eeeeeee ee eee 8,8-eeeeeee eee eeeeeee eeee e eeeee eeeeeeeeee ee eeeeeee-8,8-eeeee eee e eeeee eeeeee ee MeMMe ee eeee 8-[8,8-eee(eeeeeeeeeeee)eeeeee]eeeeeee-8,8-eeeee. Mee eeeeee 888 (8 e, 8.8 eeee) eee eeeeee ee eeeeeeeee eeeeeeee-eeeeeee MMe (88 eM) eee 88 e. Meeeeeeeeeee eeeeeee eeee eee eeeeeee eeee eee eeeeee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeee ee eM 8 ee eee eeeeeeee ee 88% ee MeMM eee Me8M eee eeee ee eeeeeee eee eeeeeee (8.88 e, 88%), eeeee eee eeeeeeee ee eeeeeeeeeee (888°M/88 Meee); eeeee: 8.88 e (88%); ee 888–888°M.
8M-Meeeee (8); Meeeeee Meeeeeeee:[888]
8-Meeeeeeeeeee (888; 8.88 e, 88 eeee) eee eeeeeeeee ee 88 M MMe (8.8 eee, 88 eeee). Mee eeee eee eeeeee ee -8°M eee e eeee eeee ee MeMM8 (8.88 e, 88.8 eeee) ee M8M (8 eM) eee eeeee eeee 88 eee. Meeee e eeeeeee 88 eee, eeee (88 ee, 8.8 eeee) ee M8M (8 eM) eee eeeee. Meee eeee eee eeeee eeee 88 eee ee e eeee ee eeeee eeeeeee (8.88 eM, 88 eeee) eee MeMe (8.88 e, 88 eeee) ee eeeeeee/M8M (88:88; 88 eM) ee -8°M. M eeee eeee ee MeMe8 (8.88 e, 8.8 eeee) ee M8M (8 eM) eee eeeee eeee 88 eee eeeeeeeee ee eee eeeeeeeee ee M8. Mee eeeeeee eee eeeeeeeeee eeeee 88°M eee 8 e eee eeee eeeeeee ee ee eee 8 e. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeee ee M8M. MM8Me8 (8 × 88 eM) eee eeee ee eeeeeee eee eeeeeee eee eee eeeeeeee eeee eeeeee eeee M8M eee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee. Meeeeeeeeeee eeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeee 8:88) ee eeee 8-eeeeee-8-(8-eeeeeeeeeee)eeeee eeeeeee (888) ee ee eee; eeeee: 8.88 e (88%); eee 8-(8-eeeeeeeeeee)eeeeeeeeeeee; eeeee: 8.88 e (88%).
8-Meeeee-8-(8-eeeeeeeeeee)eeeee eeeeeee (888; 8.88 e, 8 eeee) eee Me eeeeee (8.88 e, 88.8 eeee) eeeeeeee eeee MeMM (8.8 e, 88 eeee) eee MeMMe (8.88 e, 8 eeee) eeee eeeeee ee eeeeee ee MeMM/M8M (8:8; 888 eM) eee 8 e. Mee MeMM eee eeeeeeeeee eee MM8Me8 (8 × 88 eM) eee eeee ee eeeeeee eee eeeeeee eeeeeeee. Mee eeeeeeee eeee eeeeee eeee M8M eee eeeee, eeeee (M8MM8), eeeeeeeeeeee, eee eeeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeee 8:8) eeeeee 8M-eeeeee; eeeee: 8.88 e (88%); ee 88–88°M.
References
| [274] | Meeee, M. M., MMM; Meeeeee, M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [301] | Meeee, M.; Meeeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [320] | Meeee, M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
| [321] | Meeee, M.; Meeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [322] | Meeeeeeeee, M.; Meeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [323] | Meee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [324] | Meeeeeeeee, M.; Meeeee, M., Meeeeeeeeee, Meeee., (8888) 8, 888. |
| [325] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [326] | Meeeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeíe, M. M.; Meeeeee, M. M.; Meeee, M. M., Meeeeeeee, (8888), 8888. |
| [327] | Meeeee, M.; Meeeeeeeeeeee, M. M.; Meeee, M., Meeeeeeee, (8888), 888. |
| [328] | Meeeee, M.; Mee, M.; Mee, M.; Meeeeeeeee, M.; Meee, M.; Meeeeeeeee, M.; Meeee, M., Meeeeee, (8888), 888. |
| [329] | Meeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeee, M. M., Mee. Meee., (8888) 8, 8888. |
| [330] | Meeee, M. M.; Meeee, M.; Meeeeee-Meeeíeee, M.; Möeeeeeee, M. M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [331] | Meeeeee, M.; Me Meeeeee, M.; Meeeee, M.; Meeee, M., Meeee. Meeeee., (8888) 88, 88. |
| [332] | Meeeee, M. M.; Meeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [333] | Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeeeeee, M.; Meeee, M. M.; Me Meeee, M., Meee. Meee. Meee., (8888) 888, 888. |
| [334] | Meeeeee, M.; Meee, M.; Meeeeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [335] | Meee, M. M.; Meeeeee, M. M.; Meeeee, M., Mee. Meeee., (8888) 88, 888. |
| [336] | Meeee, M. M.; Meeeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [337] | Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [338] | Meeeeeeee, M.; Meeeeee-Meeeeeeeee, M.; Meeeeeeeee, M., Mee. M. Meee., (8888) 88, 888. |
| [339] | MeeeeMeee, M. M.; Meeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [340] | MeeeeMeee, M. M.; Meeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [341] | Meeeeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [342] | Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [343] | Meee, M.; Meeeeeee, M.; Meeeeee, M. M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 88. |
| [344] | Meeeee, M. M.; Meee, M. Me., M. Me. Meee. Mee., (8888) 88, 8888. |
| [345] | Meeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M.; Meeeee, M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
| [346] | Meee, M. M.; MeMeee, M.; Meeee, M.-M.; Meeeeee, M. M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
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