You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via47.1.4.3.1 Variation 1: Elimination from Alkyl Halides
Please login to access the full content or check if you have access via
Kostikov, R. R.; Khlebnikov, A. F.; Sokolov, V. V., Science of Synthesis, (2010) 47, 780.
The introduction of double bonds into organic systems by the elimination of hydrogen halides is a widely applicable transformation.[38] Alkene formation from alkyl halides occurs mainly as an E1, E2, or E1cb base-catalyzed process. The regio- and stereoselectivity depend on the conditions, including structural factors, solvent, type of halide, and base. Reactions of the E1 type usually occur in polar solvents and are directed by the thermodynamic stability of the formed alkene (Zaitsev rule). This mechanism is followed for tertiary, for allyl, and partially for secondary alkyl halides. Reactions of the E2 type occur for primary and secondary alkyl halides preferentially in solvents of low polarity with the use of hard bases. The selectivity of elimination reactions is generally described by the Hofmann rules. Alkene formation according to the E1cb mechanism is initiated by anion formation, and is completed by loss of a leaving group (see Houben–Weyl, Vol. 5/1b, pp 11–44, 184–172).[39]
Mee eeeeeeeee ee e M=M eeee ee β-eeeeeeeeeee eeee eeeee eeeeeee ee ee eeee-eeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee (Meeeee 88). Mee eeeeeeeee ee eeee eeeeeeeee eee eeee eee eeeeee ee eeeeeeeee eeeeeeee. Meeeeeee eeeeeeeeee eeeeeeeeee eeeeeeeeee ee eeee eee eeeeeeee eeee eeee eeeeeeee ee eeeeeeeee eee eeeeeee ee eeeeeeeeeeeeeeee (eee eeeeeeeeeee ee Meeeeee eee Meeeeee eeeeeeee eeee eee eeeeee) eee eeeeeeeeeeeeeeeee (eeeeeeeeee eee M- eee M-eeeeeee eeee eee ee eeeeee). Meee e eeeeeeeeeee eeeee ee eeee, ee eeeeeee eeeee eeeeeeeee eee eeeeeeeeee eeee eeeeeeeeeeeee, eeee ee eeeeeee eeeeeeeee eeeeeeeeee, eeeeeeee eeeeee (ee eeee eee ee eeeeeeeee eeeeeeeeeeee eeeeeeeee), eee eeee eeeeeeee eeeee.[88]
Meeeee 88 Meeeeeeee ee M=M Meeee ee β-Meeeeeeeeee ee MM eeee Meeee Meeeeee
Mee-8-eeee (Meeeeee eeeeeeee) eee eeeeee eeee eeeeeee eeeee eeeeeeee eee eeeeeeeee eeee-eeeeeeee ee eeee-eeeee eeeeeee. Meeeeee eeeeeeee eee eeeeeeee ee eeee eeeeee ee eeeeeeeeeee eeee eeeeeeeee eee eeeeeeee eeeeeeeeee. Meee, eeeeeeeee ee 8-eeeeeeeeeeee eeee eeeeeeeee eeeeeeee ee eeeeeeeee eeeeeee eeeeeee e 88% eeeee eeeee ee eeee-8-eee eee eeee-8-eee, ee e eeeee ee 8:8 eee eeee ee M/M eeeee ee 8.8:8 ee eee eeee-8-eee.[88] Mee eeeeeeeeeeeeeeee eee ee eeeeeeee, eeeeeee, ee eeeee eee eeeeeeeeee eeee eeeeeeeee eeeeeeeee eeee-eeeeeeee eeeeeee ee eeeeeeeee eeeeeeee (Meeee 8).[88–88] Me ee eeee eeeee eeee eeee eeeeeeee ee eee eeeeeeeeeee eeeeee eeeeeeeeeee ee eeeeeeeeee ee eeeeeeeeeeee ee eeeee eeeeeee. 8-Meeeeeeeeee eeee eeeeeeeee eeee-eeeeeeee–eeee-eeeee eeeeeee/eeeeeeee eeeeeeeee eeeee e eeeeeee eeeeeeeeee 88% ee eee-8-eee eee 88% ee eee eeeeeeeeeeee eeeeeee; eeeeeee, eeee 88% ee eee eeeeee ee eeeeee eeee eeeeeeeee eeeeeeeee–eeeeeeee/eeeeeeee eeeeeeeee.[88] Me eeeeeee eeeeeeee, ee eeeeeeee ee eee eeeeeeee ee eee eeee eeeeee ee eeeeeeee ee M/M eeeeee, ee ee eee eeeeeeee eeeeeeeeee ee eee eeeeee eeee eee eeee eeeeeeeee eeeeee eeee (Meeee 8).[88] Meeee eeeeeeeeee eeee eeeeeee eeee ee eeeeeeeeeee eeeeee eeee eeeeeeeeeeee, eeeeeeee eeee eeee eeeeee ee eeeeeeeeeee eeeeeeee, eeeee eee eeeeeeeeeeeee 8-eeeeeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeee eeeeeeee eeeeeeeeeeeee.[88]
Mee eeeeeeeeeeeeeeee ee eee eeeeeeeeeee eeeeeee ee eee eeeeeee. Meee 8-eeeeeeeeeeee eee eeeeeee eeee eeeeeeee eee ee eeeeeeeee eeeeeee, eee eeeeeeeeee ee eeee-8-eee ee eee eeeeee eeeeeee eeeeeeeee ee eee eeeee eeeeee (88%) < eeeeeee (88%) < eeeeeeee (88%) < eeeeeeee (88%). Mee eeeeeeee ee eeee-8-eee eeeeee eeee ~8 ee 8%. Mee 8-eeee-8-eeeeeeeeeeeee eeeee eee eeee eeeeeeeeee, eee eeeeeeeeee ee 8-eeeeeeeee-8-eee ee eee eeeeee eeeeeee eeeeeeeee ee eee eeeee eeeeeee (88%) < eeeeeeee (88%) < eeeeeeee (88%). Me eeee eeeeee, eee eeeeeeee eeeeeee eeeee Meeeeee-eeee eeeeeeee (>88% eee-8-eee).[88]
Mee Meeeeee eeeeeeee, eee-8-eeee (e.e., 88), eee eeeeeeee eeee eeeeeee eeeee eeeeeeee eeee eeeeeee eeeeeeeeeeeeeeee ee eeeeee eeeeeee ee eeeeeeeeeee eeeeeeee (Meeee 8).[88–88] M eeeeee eee eee eeeeeeeeeee ee eeeeeeee eeeeeee eeee eeeee eeeeeee eeeee eeeeee eeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee ee eeee eeeeeeeeeee eee eeee eeee eeeeeeee.[88] Meeeee eeeeeee–eeeeeeeeeeeeeeeeeeee eeeeeeee eee eeeeeee eeeeeeeeee eeeeeeee ee eeeeee eeeeeee–eeeeeeeeeeeeeeeee:[88] eeeeeeeeeee eeeeeeee eee eeeeeeee ee eeee eeeeee eeee eeee eeeeeeeeee eeeeeeeee eeeeeeee eeeeeeeee, eee eee eeee eeee eeeeeee eee eeee eeee 8-eeeeeeeeeeeeeeeee. Meeeeeeeeee ee eeeeeeee eeee eeeeeeeeeeeeeee ee e eeeee ee 88%, eee 8-eeeeeeeeee eeeee eee-8-eee ee 88% eeeee.[88]
Meeee 8 Meee-Meeeeeeee Meeeeeeee ee Meeeeee eeee Meeee Meeeeee[88–88,88–88]
Meeee Meeeee | Meeeeeeeee | Meeeee(e) | Meeee (M/M) eee Mee-8-eee | Meeee (%) | Mee |
---|---|---|---|---|---|
e-MeMM, e-MeMM, 88°M | 8.8:8 | (88:88)e | [88] | ||
MMMM, eeeeeee, 88°M | 8.8:8 | 8 + 88e | [88] | ||
MeMM, MeMM | 8.8:8 | 88 + 88 | [88,88] | ||
MeMM, MeMM | 8.8:8 | 88 + 88 | [88] | ||
e-MeMM, e-MeMM, 88°M | 8.8:8 | (88:88)e | [88] | ||
MMMM, eeeeeee, 88°M | 8.8:8 | 888 | [88] | ||
e-MeMM, e-MeMM, 88°M | 8.8:8 | 888 | [88] | ||
Me8MMe, eeeeeee, 88°M | 8.8:8 | 888 | [88] | ||
MeMM, MeMM | 8.8:8 | 88 + 88 | [88] | ||
MeMM, MeMM | 8.8:8 | (88:88)e | [88] | ||
MeM, MMMM | – | 88 | [88] | ||
e-MeMM, e-MeMM, 88°M | 8:8 | (88:8)e | [88] | ||
MMMM, eeeeeee, 88°M | 88:8 | (8:88)e | [88] | ||
e-MeMM, e-MeMM, 88°M | 88:8 | (88:88)e | [88] | ||
MMMM, eeeeeee, 88°M | 88:8 | (8:88)e | [88] | ||
e-MeMM, MMMM | – | 88 | [88] | ||
MMM, MMM | – | 88 | [88] | ||
e-MeMM, MMMM | – | 88e | [88] | ||
MeM, MMMM | – | 88 | [88] | ||
MeMMe (88% eeeeee), MeMM | – | –e | [88] | ||
e-MeMM, MMMM | – | 88e | [88] | ||
e-MeMM, e-MeMM/MMMM | – | 88e | [88] | ||
MMM, MMM | – | 88 | [88] | ||
e-MeMM, MMMM/eeeeeee | – | 88e | [88] |
e Meeee ee eee-8-eee/eee-8-eee ee eee eeeeeee eeeeeee.
e Mee eeeeeeeeeeeee eeeee eeee-eeeee eeeee eee eeee eeeeeeee.
e Meeee eee eeeeeeee.
e Meeee eeee eeeeeeee eeeeeee.
Meeeeeeee eeeeeeeeeeeeeeee eeeeeeee eee Meeeeee eeeeeee eee ee eeeeeeee eeee 8-eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee eee eeeeeee eeeee M8-eeeeeeee eeeeeeeeee eeee e eeee eeee (eee eeee) eeee.[88,88]
Meeeeeeeeeeeeeeeeee (88) ee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeee eeeee eeee eeeeeeeeee ee 88% eeeee eeeee 8,8,8-eeeeeeeeeeeeeeeee (88) ee e eeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeeeeee[88]
Meeeeeee eeeeeee eeeeeee eeeee eeee ee eeeeeeeeeeeee, M,M-eeeeeeeeeeeeeee, eeeeeeee, eee eeeeeeeee eeee eeee eeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeee, eeee eeeee eeeeeee eeeeeeeeeeeeee eeeeee. Meeeee eeeeeeee eeeeeeee eeeeee eee eeeeeee ee eeeeeeeeee eee ee eeeeeeeee eeee.[88] Meeee eee 8888e, 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee (MMM) eee 8,8-eeeeeeeeeeee[8.8.8]eee-8-eee (MMM) eeee eeeeee eeeeeee eeeeeeeeeeeeeeeeeee eeeeeeee eeeee ee eeeee eeeeeeeeeeeeeee eeeeee eee eeeeeee eeeeeeee. Meeeeee, eeeee eeeeeeee eeeeeeeeee eeeeeee eeeeeee eee eeee ee eeee ee eeeeeeeeeeeeee eeeeee. Meeeeeee, eeeeee eee eeeee eeee eeeeeeee.[88]
Mee eeeeeeeeeee ee eeeeeee 88 eee 88 eeeeeeee eeee eee eeeeeeeeeeeeeeeeeee ee eeeeeeeee eee eeeeeeee eeeeeeeee eeeeeeee, eeeeeeeee, eee eeeeeee eeee eee eeeeeeee eeeee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee eee eeeeeeeee ee Meeee 8.[88] Mee eeeeeeeee eeeeeeee, eee eeeeee ee eee eeee eeeeee eeeeeeeeeee eeeeee (Meeeeee eeeeeee) ee eee eeee eeeeeeeeeee eeeeee (Meeeeee eeeeeee) eee ee eee eeeee ee 8:8; eee eeeeeeee eeeeeeee, eee eeeeeeeeeeeee eeeeee eee 8–8:8 eee eeeeeeeee eeeeeee eee >8:8 eee eeeeeeeeee eeeeeeee. Mee eeeeeeee ee e eeeeeeee β-eeeeeeee eeeeee eee Meeeeee eeeeeee. Meeee eeeeeeeee ee eeeeeeeeee ee eee eeeeeeee eeeeeeeee eeeeeeee eee eeee e eeeee eeeeee eeee eee eeeeeeeeeeeeeeee. Mee eeeeeeeeee ee Meeeeee eeeeeee eeeeeeeee ee eee eeeee eeeeeeee < eeeeeee < eeeeee, eeeee eee M/M eeeee eeeeeeeee ee eee eeee eeeee eeee 8.8:8 ee 8:8 (Meeee 8).[88–88]
Mee eeeeeeeeeeee eeeeeeeee eee-eeeee eeeeeeeee eeeeeeeeeeeeeeeeee, [M(MeMMM8MM8)8M, 88], ee eee eeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee eee eee eeeeeeeeee ee eeeeeee eee eeeeeeeee eeeee eeeeeee eeee eeeeeee. M eeeeee eee eee eeeeeeee ee eeeeeeeeeeee ee e eeeeeee eee eee eeeeeee eeeeeeeee eeeeeeee eeeeeeee eeeee ee eeeeeeeee. Me eee eeeeeeeeee eeee eeeeeeeee 88 ee e eeeeeeee eeeeeeeeeeeeeeeeeee eeeee eee eeeeeee eee eeeeeeeee eeeee eeeeeee (Meeee 8).[88] 8-Meeeeeeeeeee eeeee eeee-8-eee (88%) eee (M)-eeee-8-eee (88%) eeee eeeeeeeeeeeeeeeeee, eeeee ee eeeeeeee ee eeee eeee eeeeeeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeeee eeee eeeeee eeeeeee.[88]
Meeee 8 Meeeee Meeeeeeee eeee Meeeeeeee eee Meeeeeee Meeee Meeeeee Meeee Meeeeeee Meeeee[88–88]
Meeee Meeeee | Meeee eee Meeeeeeeee | Meeeee | Meeee (M/M) ee Mee-8-eee | Meeee (%) | Mee |
---|---|---|---|---|---|
MMM, 88°M, 88 eee | 8.8:8 | 8 + 88 | [88] | ||
MMM, 88°M, 88 eee | 8.8:8 | 88 | [88] | ||
MMM, 88°M, 88 eee | – | 88 + 88 | [88] | ||
MMM, 88°M, 88 eee | – | 8 + 88 | [88] | ||
MMM, 88°M, 88 eee | 8.8:8 | 8 + 88 | [88] | ||
eeeeeeeeeeeeeeeeee (88)e, ee, 88 e | – | 88 | [88] | ||
eeeeeeeeeeeeeeeeee (88)e, ee, 88 e | – | 88 | [88] | ||
MMM, 88°M | – | 88 + 88 | [88] | ||
MMM, 88°M, 88 eee | – | 8 + 88 | [88] | ||
MMM, 88°M, 88 eee | – | 8 + 88 | [88] | ||
MMM, 88°M, 88 eee | 8.8:8 | 88–88 + 88–88 | [88,88] | ||
eeeeeeeeeeeeeeeeee (88)e, ee, 88–88 e | – | 88 + 88 | [88,88] | ||
MMM, 88°M | – | 88 | [88] | ||
MMM, 88°M, 88 eee | – | 8 + 88 | [88] | ||
MMM, 88°M | – | 88 + 88 | [88] | ||
MMM, 88°M, 88 eee | – | 8 + 88 | [88] |
e Mee eeee eeee ee eeeeeeee eeee eee eeeeeeeeeeeee eee MeM.
Meee(eeeeeeee eeeeeee), MM(MM8MM8M)eM, eeeee e > 88, eee eeeeee eeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeeeeeee ee eeeeeee–eeeeeee eeeeeeeee eee-eeeee eeeeeee.[88] Meeeeeee ee 8-eeeeeeeeeee ee eeeeeee eeee 88% eeeeeee eeeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eeeee-eeeeeeee eeeeeeeee eeee ee 88-eeeee-8 ee 88°M eeeeeeee eeee eee eeeeeeeeeeeeeeeeeee eeeeeee eeee 888% eeeeeeeeeee (eeeee ee eee-8-eee/eee-8-eee = 8:8).[88]
Meeeeeee eeee eeeeeeee eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee ee eeeeeeee eeeeeeeeeeee eeeeeeeeeeee eeee. Me eee eeeeeeee ee eeeee eeeeee ee eeeeeeee eeeee, eeee eeeeeee eeeeeeeeeee e eee eee ee eeeeeeee “eeeee” eeeeeeeeeeee. M eeeeee M=M eeee-eeeeeee eeeeeeee eee eeee eeeeeeeee eeee eeeee eeeeeee eee eee(eeeeeeeeeee) eeeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee eee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee ee Meeeee Meeee Mee(eeeeeeeeeee) Meeee eee Meeeee Meeeeeee Meeeeeee[88]
Meeeeeeeee eeeeeeeee ee eeeee eeeeeee eeeeeee ee eeeee eeeeee eeeeeeee ee eeeeeeeeeeee M8 eeeeeeeee ee eeee eeeeeeeeeeee eeeeeeee, eeeee eeee eeeeeee. Meeeeee, ee e eeeeeeeeeeeee eeeeeeeeee eeeeee, eeee eeeeeeee ee eeeeeeeee eeee eee eeeeeeee eeeee eeeeeee. Mee eeeeeeeeee ee 8-eeeeeeeeeeeee (eeeeeeee eeeeee eeeeeeeee eeeee) ee e eeeee ee eeee-eeeee eeeeeeee, M8MM8MMeMe8 (M8 = Me, Me, eMe, e-Me), eeeeee eeee eee eeeee ee eeeeee eeeeeeeee eeee eeeeeeeeee eeeeee eeee ee M8: Me, 88%; Me, 88.8%; eMe, 88%; e-Me, 88%. Mee eeeee ee eee-8-eee ee eee-8-eee eeeeeee ee eee eeeeeeeee ee ee eeeeeeee ee eeee ee eee eeeeeeeeee eeeeee ee eee eee-8-eee eeeeeeeee eeee eeeeee eeeeeeeeeee eeeeeee eee M8 eeeee eee eee eeeeee eeeee: M8 = Me, 8.88:8; Me, 8.88:8; eMe, 8.88:8; e-Me, 8.88:8.[88] Mee eeeeeeeeeeeeeeee ee eeeeee eeeeeeeee eeee eeeeeeeeee ee eee eeeeee ee eeeeeeee eeeee eeeeeeee ee ee eeeeeeeeee eeee eee Meeeeee eeee. Meeeeee, eee eeeeeeeeee ee 8-eeeeee-, 8-eeeee-, eee 8-eeee-8,8,8-eeeeeeeeeeeeeeee eee eeeeeee ee eeee 88% ee 8,8,8-eeeeeeeeeeeee-8-eee eee 88% ee 8,8,8-eeeeeeeeeeeee-8-eee, eeeeeeeee e eeee ee eeeeeeeeeee ee eeeeeeeeee eeee eee Meeeeee eeee. Mee eeeeeeeee eeeeeee eeeeeeee eeee eee eeeeeeee, eeeeeee, eee eeeeee eeeeeee eee eeeeeeeeee eeee eee eeeeeeeeeee eeee eeeeeee eeeeeee e eeeeeeeee eee eeeeeeeeeeee. Meeeeeeeeeee eeeeeeeeeeee eeeeeee ee eeee eee eeee eeeeee eeeeeeee eeeeee. Meee eeeeeeeeeeee eee eeeeeeeeee ee eeeeee eee Meeeeee eeeee ee eeeeeeeeeee (Meeee 8).[88]
Meeee 8 Meeeeeeeeeeeeeee ee Meeeee Meeeeeeee eee Meeeeeeeee ee 88% Meeeeee 8-Meeeeeeeeeeee[88,88]
Meeee Meeeeee | Mee-8-eee | Mee-8-eee | Meeee (Mee-8-eee/Mee-8-eee) | Meeee Meeee (%) | Mee |
---|---|---|---|---|---|
88:88 | 88–88 | [88] | |||
88:88 | 88 | [88] | |||
88:88 | 88 | [88] | |||
88:88 | 88 | [88] | |||
8:88e | 88 | [88] | |||
88:88e | 88–88 | [88,88] |
e Meeeeee ee M- (88%) eee M-eeeeeee (88%).
e Mee eeee eeeee ee eeeeeeeeeeee ee eeeeeeee eeee eee eeeeee eee eeee eeeeeeeee.
Meeeee-eee-eeeeeeee eeeeeeeeeeee eeee 8-eeeeeeeeeeee eee eeeee ee eeeeeee eeee eeee eeee eeeeeeeeeeeeeeee (Meeeeee eeeeeeee eeeeeeeee) eee eeee M/M eeeeee eeeeeee eeee 8.8:8 ee 8.8:8. Mee eeeeeeee ee 8-eeeeeeeeee eeee eeeeee(M) eeeeeee ee eeeeeeee eeeeeeeee ee 88°M eeeee e eeeeeee ee eeeeeee (88%): (M)-eee-8-eee (88%), (M)-eee-8-eee (88%), eee eee-8-eee (8%). M eeeeeee eeeeeee ee eeeeeeee ee eee eeeeeeee ee eeee eeeeee eeee eeeeeee(MM) eeeeeee. Me eee eeeeeeeee ee 8-eeeeeeeeeee, 8-eeeeeeeeeeee, eee 8-eeeeeeeeeee eeee eeeeee(M) eeeeeee ee eeeeeeee eeeeeeeee, eee eeeeeeee ee eeeeeee eeeeeeee eeeeeee ee M-eee-8-eee (88–88%), M-eee-8-eee (88–88%), eee eee-8-eee (8–8%).[88]
Meeeee-eee eeeeeeeee eeeeeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeee ee eeeeeeee eeeee eeeeeee ee eeee eeeeee Meeeeee eeeeeeee. Meeeeeeeee ee (eeeee)-8e-eeeeeeeeeeeeeeeeeeeeeeeeee ee 88% eeeeeee eeeeeee eeeeeeee e eeeeeee ee eeeeeeeeeeeeeeeeeeeee 88 eee 88 ee e eeeee ee 88:88 (Meeeee 88).[88] Me eee eeeeeeee ee eeeeee(M) eeeeeee, eee eeeee eeeeeee ee 8:88 (eee Meeeee–Meee, Mee. 8/8e, ee 88–88, 888–888).
Meeeee 88 Meeeee-Mee Meeeeeee Meeeeeeeee ee (eeeee)-8e-Meeeeeeeeeeeeeeeeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeeeee-8-eee (88); Meeeeee Meeeeeeee:[88]
Me e eeee ee 8-eeeeeeeeeeeeeeee (8.88 e, 8 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeee e 8 M eeee ee e-MeMM ee MMMM (88 eM, 88 eeee). Mee eeeee eeee eeeeee eeeeee eee eeeeeeee eeee. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee (Meeeeeee, eeeeeeeee eeeee). Mee eeeee 888 eM eeeeee ee eee, eeeee ee eeeeeeeeeeeeeeee eeeeeee eee eeeeeee ee eee eeeeeeeee eeeee eeeeeeeee; eeeee: 8.88 e (88%); eM88 8.8888; MM (MM8) ν̃eee: 8888, 8888, 888, 888 (eeeee) ee-8. Meee eee eeeeeeeee eeeee/Me8M (8:8) eeeeeeeee, eeee-eeeee eeeeeeeee eeeee eee eeeeeeee; eeeee: 8.88 e (88%); eM88 8.8888.
88,88-Meeeeeeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[88]
MMM (8.8 eeee) eee eeeeeeee ee MMM (8 eM) eeee eMe8MM (888 ee, 8.8 eeee) eee e 8.8 M eeee ee MeMe ee eeeeee (8.8 eM, 8.8 eeee). Meeee 8 eee, 8-eeeee-88,88-eeeeeeeeeeeeeeeeee (888 ee, 8.88 eeee) ee MMM (8 eM) eee eeeee. Mee eeee eee eeeeeee eeeeeeeee, eeee eeeeeee eeee eeeeee, eeeeee eeee 88% M8MM8 eee eeee eeeee, eeeee, eee eeeeeeeeeeee. Meeeeeeeeeeeee eeee eee eeeeeee; eeeee: 888 ee (88%); 8M MMM (MMMe8, δ): 8.88 (e, 8M), 8.88 (e, M = 88 Me, 8M), 8.88 (e, M = 88 Me, 8M), 8.8 (e, 8M), 8.8–8.8 (e, 88M), 8.88 (e, 8M), 8.88 (e, 8M).
Meeeeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
M eeee ee 8-eeeee-8-eeeeeeeeeeeeeeee (888 ee, 8 eeee) eee 8,8,8-eeeeeeeeeeeeeeeee (88; 888 ee, 8 eeee) ee MeMM (888 eM) eee eeee ee ee eee 8 e. M8M (888 eM) eee eeeee, eee eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee, eeeee, eee eeeeeeee ee 88°M; eeeee: 888 ee (88%); ee 888°M; 8M MMM (MMe8, δ): 8.88 (e, 88M, 8MM + 8MM8), 8.88 (e, 8M, 8MM), 8.88 (e, 8M, =MM8).
Meeeeee 88 eee 88; Meeeeee Meeeeeeee Meeee 8,8-Meeeeeeeeeee[8.8.8]eeeee-8-eee:[88]
MMM (8–88 eeee) eee eee eeeee eeeeeee (8–88 eeee) (eeeeeee eeeeeeeee, eeeeeee eeeee eeeeeee eeeeeeee) eeee eeeee eee eeeeee ee ee eee eeee ee 88°M. Meeeeee eee eeeeeeee eeee eeeeeeeee eee 8–88 eee eeeee eee eeeeeeeeee (eeeee 8 eee) ee e eeeeeeeee eeeeeeeeeee ee eeeee. Mee M8 eeeeeee eeee eeeeeeeee eee eeeeeeeee ee e eeee eeee (eee eee/eeeeeee). Mee M8–M8 eeeeeee eeee eeeeeeeee (eee-M8 eeeeeee) ee eeeeee eeeeeeee ee ee. 8 Meee. Meeeee eeeeeee eeee eeeeeeeee eeee eee eeeeeee ee eeeeeeeeee eeee Me8M eeeeeeee ee eeeeeeeeeee ee eee eeeeeee. Meeeeeeee eeeeeeeee eeeeeeee ee e eeeeeee ee 8%; eeeee: 88–88%.
Meeeeee 88 eee 88; Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeeeeee:[88]
Me e eeee ee eeeeeeeeeeeeeeeeee 88 (8.88 eeee) ee MeMM (88 eM) eee eeeee ee 88°M, eeeee M8, eee eeeee eeeeee (8.88 eeee) ee MeMM (8 eM), eee eee eeeeeee eee eeeeeee eee eee eeeeee eeee (Meeee 8). Meee, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eee eeeeee eeee M8M (8 × 88 eM) eee eee eeeeeee eeeee eee eeeee (Me8MM8). Meeeeeeeeeeee ee eee eeeeeee eeeeeeee eeeee eeeeeee eeeeeeee eeeeeeee MMM-eeee eeeeeee; eeeee: 88–88%. Meeeeeee 88 eee eeeeeeeeeee eeee eee eeeeeee eeeeeeeee eeeee eee eeeeeeeeee.
References
[30] | MeMeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[38] | Meeeeeeee, M., Me Mee Meeeeeeee ee Meeeeee, Meeeee-Meeeeee eee Meeeee: Meeeeeeeee M, Meeee, M.; Meeeeeeee, M., Mee.; Meeee: Mee Meee, (8888); eeee 8, e 8888. |
[39] | Meeee, M.; Meeeeee-Meeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 888–888. |
[40] | Meeeeeeee, M.; Meeeee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[41] | Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[42] | Meee, M. M.; Meeeee, M. M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[43] | Meeee, M. M.; Meeeeeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[44] | Meeeeee, M. M.; Meeee, M. M.; Meee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[45] | Meeeee, M.; Meeeeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[46] | Meeeeeee, M. M., Me.; Meeeeeeeeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[47] | Meee, M. M.; Meeeeee, M.; Meee, M. M. M.; Meeeeeee, M. M.; Meeeeee, M., Mee M. Meee., (8888) 88, 888. |
[48] | Meeee, M.; Meeee, M.; Meee, M. M. M.; Meeee, M. M., M. Meee. Meee., (8888) 88, 8888. |
[49] | Meeee, M.; Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[50] | Meee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[51] | Meee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeee, M., Meee. Meee. Meee. Meee-Mee, (8888) 88, 888. |
[52] | Meeeeee, M. M.; Meeeeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[53] | Meeeeeee, M., Meeee. Meeeee., (8888) 88, 8888. |
[54] | Meee, M. M.; Meee, M. M.; Mee, M. M.-M.; Meeeeee, M. M.; Mee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[55] | Meeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888), 888. |
[56] | Meeeeeeeee, M. M.; Meeee’eeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M., Me. Mee. Meee., (8888), 88, 888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
[57] | Meeeeee, M.; Möeeee, M.; Meeee, M., Meeeeeeee, (8888), 888. |
[58] | Meeeeee, M., M. Mee. Meee., (8888), 88, 8888. |
[59] | Meeeeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[60] | Mee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[61] | Meeeeee, M.; Möeeee, M., Meeee. Meee., (8888) 88, 88; Meeee. Meee. Mee. Me. Meee., (8888) 8, 88. |
[62] | Meeeee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[63] | Meeee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[64] | Meeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[65] | Meeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[66] | Meeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[67] | Meeeeeee, M. M.; Meeeee, M.; Meee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 88.
- 8.Meeeee-Meee, (8888) M 8e, 888.