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1.12.6.1.1 Halogenation (Chlorination, Bromination, Fluorination)

DOI: 10.1055/sos-SD-234-00262

Bietti, M.; Dénès, F.Science of Synthesis: Free Radicals: Fundamentals and Applications in Organic Synthesis, (20211555.

Halogenation of alkanes can be achieved upon irradiation or thermal initiation in the presence of molecular halogens X2 (X = Br, Cl, F). Chlorination of alkanes can be achieved upon irradiation with molecular chlorine[‌211‌] or sulfuryl chloride.[‌212‌] Important solvent effects have been observed in the chlorination of short-chain alkanes. In this case, the selectivity of the chlorination is improved in aromatic solvents, in which the chlorine radical is assumed to form a complex with the solvent, switching the HAT step from an exothermic to an endothermic process.[‌213‌‌215‌] Several issues arise from the high reactivity of the chlorine radical, including problems of site selectivity and product chemoselectivity (di- and polychlorination). Reaction parameters (e.g., molar ratio, light power, reaction times) need to be controlled to favor monochlorination. In this respect, the process is relatively clean with cycloalkane substrates when conducting the chlorination with sulfuryl chloride under microflow conditions.[‌216‌]

Meee MMM ee e eeeeeee eeeeeee eeeee eeeeeeeeeee, eeeeeeeeeee ee eeeeeee eee eeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeee.[‌888‌] Meeeeee eeeeeeeeeee eeeee M-eeeeeeeeeeeeeeee (Meee–Meeeeee eeeeeeee)[‌888‌‌888‌] eee ee eeeeeeeee eeee eeeeeeeeeee ee eeeeeee, eeeeeee ee eee eeeeeeee ee e eeeeeee eeeeeeeee. Me eeeeeee eeeeeeeee (Meeeeee 8.88.8.8), eeeeee eeeeeeeeeeeee ee eee eeeeeee ee eeeeee ee eeeee eee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeeee, eee eeeeeeeeeeee, eeee ee eee eee ee eee eeee eeeee eeeeeee (eeeeeeeeeeeeeee)eeeeeee, eee eeee eeeeeeee.[‌888‌] Me eeeeeeeee ee Meeeeee 8.88.8.8, eee eeeeeee eee eeeeeeee eeeeeeeeeee eeee M-eeeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeee eeeeeee e eeeeeeeee eeeeeeeee eeeeeeee ee Meeeeeeeee,[‌888‌,‌888‌] eeeee M-eeeeeeeeeeeeeeee eeeeeeee e eeeeee ee eeeeeeeee eeeeeee. Me eeee eeee, eee eeeeeee eeeeeee eee eeeeeeeee eeeeeee eee eeeeeeeeeee eee MM eeee eeeeeeeeee eee MMe eeee eeeeeeeee, eeeeeeeeeeee. Mee eeeeeeeee eeeeeee eeeeeeeeeeee ee eee eeee ee eeeeeeeeeeee eeeeeee, eee eeeee MMM eeee eeeeee MM eeeee ee eee eeeeeee eeeeeee ee eeeeee eeeeeeeeeee. Meee, eee eeeeeee eeeeeeeee e eeeeeeee-eeeeeeee eeeeeee (eeeeeeeeeeee eeeeeee) ee eee eeeeeeee-eeee-eeeeeeeeeee eeeeeee (Meeeeeeeee eeeeeeeee) ee eeeeeeeeeee ee eee eee ee e eeee eeeee eeeeeee (e.e., eeeeeeeeeeeeeee, eeeeeeeeee, eeeeeeeeeeee), eeeee eeeeeeeee eee eeeeeeeeee ee M-eeeeeeeeeeeeeeee. Mee eeeeeeeeeeee ee e eeeeeeeeeeee eeeeeee eeeee eeeee eeeeeeeeee ee eeeeeeeee ee eee eeeeeeeee ee 8-eeeeeeeeeeeeee eeeeeeeeee eeeeeeeee eeee e eeeeeeeeeeeee eeeeeee.[‌888‌] Mee eeeeee ee eeeeeeeeeee ee eee eeeeee eeeeeeeee ee eee eeeeee-eeeeeeee eeeeeee eeeeeeeee eeee eee eeeeeeeeeeeee, ee eeee ee e eeeeeeeeee eee eeeeeeeeee eeeeeee, eeeeeeeee ee 8.8 eM · eee−8 ee eee M8M8 eeeee.[‌888‌]

Meee eeeeeeeeeeeee ee eee eeeeeeee-eeeeeeee eeeeeee eee eeee eeeeeee ee eeee eeeeeeeee ee eeeeeeeeeeee eeeeeeee (eeeeeeeeee eee ee e eeeeeee eeeeee ee eee eeeeeeeeeeee eeeeeee),[‌888‌] eee, ee e eeeeee, eee eee ee M-eeeeeeeeeeeeeeeee (8-eeeeeeeeeeeeeee-8,8-eeeeee) eeeeeee ee M-eeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee ee eeeee eeeeeeeeeee eeeeeeee eeee eeeeeeeee eeeeeeeeee eee ee eee eeeeeee eee eeeeeeeeeeeee eeeeeee.[‌888‌] Mee eee ee e eeeeeeeeeee eeeeee eeee eeeee eeeeeee eeeeeeee eeeee (e.e., 8,8-eeeeeeeeeeeeee), eee eeeee ee e eeee eee eeeeeeeee eeeeeee, ee eeee ee eee eee eeeeeee eeeeeee, eeee eeeeeeee eee eeeeeeeeee eeeeeeeee eeeeeeeee eeeeeee eeeeeeee.[‌888‌] Meeeeeeeeeee eee eeeeeeeeeee ee eeeeeee eee ee eeeeeeee eeee M-eeeeee-8,8-eeeeeeeeeeeeeeeeeee eee M-eeeee-8,8-eeeeeeeeeeeeeeeeeee, eeeeeeeeeeee. Meeeeee eeeeeeeeeee eeeeeeee eee eeeeeeee eeee eeee eeeeeeee, eeee eeeeee eee eee eeeeeeeeeee ee eee eeeeeeeeeeee ee eeeeeeee eee eeeeeee eeeeeeee eee eee eeeeeeeeeeee ee eeeeeeeeeeee MM eeeee eeeee eeeee eeeeeeeeee. Meee eeeeeeeee eeee eee eeeeeeeeeeee ee eeeeeeeeee eeeeeeeeee eeee MM eeeee (eeee ee eeeeeee eee eeeeeeee eeeeeeeeee), eee eeeee MMM ee eee eeeeee eeeeeee ee eeee eeeeeeeee ee eeeeeee.[‌888‌] Mee eee ee eeeeeeeeee eeeeeeee eee eeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee eee eee Meeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeeee ee ee eeeeee ee eeeeeeeeeee ee eeee-eeee eee eeeeeeeee ee eee eeeeeeee-eeeeeeee eeeeeee eee eeee eeeeeee eee eeeeeeeeeee.[‌888‌]

Meeeeeeee ee ee. eeee ee-eeeeeeeeeeee eeee eeeeeeeee eee eeeeeeeee e eeeeee ee eeeeeeee M-eeeee eee M-eeeeee eeeee eeeeeeee ee eeeeeee eee eeeeeeeee eeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeee MM eeeee.[‌888‌] Mee eee ee eeeeeeee M-eeeee eeeeee eeeee eeeeeeeee eeeeeee eee MM eeee eeeeeeeeeee. Meee eeeeeeeeeee eeee eeeeeee eeeee, eee eeee MMe eeee ee eee eeeeeeee M-eeeee eeeee (e.e., 88) ee eeeeeee eee eeeee e eeeeeee eee eeeeee eeeeeee eeeeee. Me eeeeeee eeeeeeeee, eee eeeeeee eeeeeee ee eee eeeeeeeeeeee eeeeeeee ee eeeeeeee eeeeeeee eeeee eeee eeeeee MM eeeee; eeee, eee eeee eeeeeeee eeeeeeee-eeeeeeee eeeeeee eeeeeeee MMM. Meeeeeeeee eeeeeee eeeeeeee eeee eee eeeeeee M-eeeee eeeeeee eeeee eee eeeeeeeeee eeeeeee eee ee eeeeee eeeeeee eeee eeeeeeee eee eeeeeee eeeee, ee eeeeeeeeee eeeeeeee ee Meeeeeeeee. Me e eeeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeeee, eee eeeeeeeeeee ee eee eee eeee ee eeee eeeeeeee eeeee M-eeeeeeeeeeeeeeee. M eeeeeeee eeeeeee ee eeeeeeeeeee ee Meeeee 88 eeee eee eeeeeeeeeee ee eeeeeeeeeeeeeeeee. Me eeee eeee, eeeeeeeeeee eeee M-eeeeeeeeeeeeeeee (MMM, MMMM, 88 °M, eeee eeeeeeeeee) eeeee e eeeeee eeeeeeeeee eee MMM eeee eee eeeeee, eeeeeeee, MM eeee (ee. 88% eeeeeeeeeee eee eee eeeeeeee eeeeeeee). Me eeeeeeee, eeeee eee Meeeeeeee eeeeeeeee eeee eeeeee ee eee eeeeeeee eeeeeee eee eeeeeeee, eeee eee eeeee eeeeeeee eeeee eeeeeeee eee MMM eeee eee eeeeeeee eeeeeeeee MM eeeee (88.8% eeeeeeeeeee eee eeeeeeeee eeeeeeeee) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee Meeeeeeeeee ee Meeeeeeee MM Meeee[‌888‌]

Mee eee ee eee eeeeeeeeeeeee M-eeeeee eeeee eeeeeeee (e.e., 88) eeeeee eee eeee eeeeeeeeeee eeee-eeeeeeeee eeeeeeeeeeeee ee ee eeeeeeee (Meeeee 88).[‌888‌‌888‌] Meeeeeee ee eeeeeeeeeeee eeeeeeeee eeeee eeeeeeeee eeeeeeee ee M-eeeeeeeeeeeeeeeee (eeeee eeeeeeeeee eeeeeeee Meeeeeeeeeʼe eeeeeeeee), eeeee eee eeeee ee eeeeeee eeee eeee eee eeeeeeeeee eeeeeeee, eee Meeeeeeee eeeeeeee eeeeee eee eeee eeeeeeeee eeeeeeeeeeeeeeeee eeeeeeeee, eeeee eeee e eeeee eeeeee ee eeeeeee. Mee eeeeeee, 8-eeeeeeeeeeeeeeeee (88) ee eeeeee eeeeeeee ee e eeee eeeee eeee (+)-eeeeeeeeeee ee 88% eeeee. Mee eeeeeeeeeeeee eee eeeeeeeee eeeeeee eee ee eee eeeeeeee ee e eeee (eeeeee eeeeeeeee), eeeee eeeeeeeeee eee eeeeeeee eeeeeeeeee eeeeeeee eeee e eeeeeeee eeeeeee eeeeee ee eee eeeeeeee ee eeeeee ee eeeeeeeeeeee eeee.

Meeeee 88 Meee-Meeeeeeee eee Meeeeeeeeeeeeee Meeeeeeee MM Meee Meeeeeeeeeee ee Meeeeeeeeee[‌888‌]

Mee eeee eeeeeeeeeee ee eee eeee eeeeeeee ee eee eeeeee eeeeeeeeee ee eee eeeeeeeee MM eeeee, eee eeee ee eee eeeeeeeee ee eee eeeeee eeeeeee eeee eeeeeeeee eee eeeeeeee eeee. Meeeee, eeeeeeeeee eeeeeeeeeeee ee eee M-eeeeee eeeee eee eeeeeeeee ee eeee eeeeeee eee eeeeee eeeeeeeeeee, ee eeeeeeeeeee eeee eee eee ee eee eeee eeeeeeeeee eeeeeeeee M-eeeeee eeeee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee eee Meeeeeeee ee eee M-Meeeee Meeee MMM Meeeeee[‌888‌]

Meeeeeeeeee 88

M-Meeeee Meeee MM Meeee (%) Meeeeeeeeee (Me/Me) Mee
88 e.e.e 88:88 [‌888‌]
88 88 88:88 [‌888‌]

e e.e. = eee eeeeeeee.

M eeeeeeee eeeeeee ee eeeeeeee ee Meeeee 88 eeee eee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M-Meeeee Meeee Meeeeeee Meeee (%) Meeeeeeeeee (Me/Me) Mee
88 e.e.e 88:88 [‌888‌]
88 88 88:88 [‌888‌]

e e.e. = eee eeeeeeee.

Mee eeeeeeeeeee ee e eeeeeeeeeeee eeeeeeeeee eee eee e eeeeeeeee eeeee, eeeee eeeeee ee ee eeeeee-eeeeeeee eeeeeee eeeeee, eee ee eeee eee eee eeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeee MM eeeee.[‌888‌] Me eeee eeee, eeeeeeeeeee ee eeee eeeeeeeee eeeee eeeeeee eeeeeeeeeeeee ee eee eeeeee ee eee eeeeeee eeee ee eeee eee eeeeee-eeeeeeee eeeeeee, eeeeeee M-eeeeeeeeeeeeeeeee ee eeee ee eeeeeee eeee ee eeeeeeeee e eeeeeeee eeee. Meee eeeeeeeee eee ee eeeeeee ee eeeeeee eeeeeeeee, eeeeeeeeeeee (eee eeeee), ee eeee ee MM eeee eeeeeeeee.[‌888‌]

Meeeeee eeeeeeeeeeee ee eeeeeeeee MM eeeee eeeee Meeeeeeeeee [8-(eeeeeeeeeeee)-8-eeeeee-8,8-eeeeeeeeeeeeeee[8.8.8]eeeeee eee(eeeeeeeeeeeeeeeee)] ee eee eeeeee ee eeeeeeee eeee ee eeeeeeeeee eeee eee eee ee eeeee-eeeeeee eeee eeeeeee (eeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeee) ee eeeeeeee eee eeeeeeee eeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee Meeeeeeeeeee eee MM Meeeeeeeee eeee Meeeeeeeeeee Meeeeeeeeeee[‌888‌]

Meeeeeeeeee eee eeee ee eeee ee eeeeeee eeeee eeeeeeeee ee eeeee ee eeeeee ee eeee eee eeeeee ee eee eeeeeeee eeee eee eee eeeeee ee e eeeeeee eeeeeee ee eeeeeee eee MM eeee eeeeeeeeee. Mee eeeeeeee, eee eeeeeeeee ee Meeeeeeeeee eeee e eeeeee(M) eeeeeeee eeeee eee eeeeeeeeeeeee eeeeee eeeeeee eeeeee, eeeee ee e eeeeeeee eeeeeeeeeeeee MMM eeeeeee eeee eee eeeeee eeeeeeee e eeeeeeee eeee eeee eeeeeeeee MM eeeee. Mee eeeeeeeee eeeeeeeeeeee eeeeee-eeeeeeee eeeeeee eeee eeeeee eeee Meeeeeeeeee ee eeee eee eeeeeeeeeee eeeeeeee eee e eee eeeeee eeeeeee eeeeee eeee eeeeeeee eee eeeeeee eeeee (Meeeee 88).[‌888‌‌888‌] Mee eeeeeeee eeeeeeeee ee Meeeeeeeeee eeeeeeeee α-MM eeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeee eeeeeee eeeeee, eeee eeeeeeee eee eeeeeeeeeeeee ee eee eeeeeeee eeeeeee ee eeee ee eee eeeeeeeee eeeeeeee ee eee eeeeee-eeeeeeee eeeeeee eee MMM.

Meeeee 88 Meeeeeeeeeee Meeee ee MMM ee e Meeeeeeeeee-Meeeeee Meeeee Meeeeee Meeeee[‌888‌‌888‌]

Mee Meeee eeeee eeeeeeee e eeeeeee eeeeeeeee ee eeeeeee eee eeeeeeeeeeee ee MM eeeee, eeeee ee eeee eeee ee eeeeeeeeeeeeeee eeeeeeee. Me eeee eeeeeeeee eee eeeeeeee ee eeeeeeeee ee eee eeeeeeeee ee eeeeee eeeeeee (88 eee%) ee eeee e MM8 eeeeeee, eeeee ee eeeeeeeeeeee eeeeeeee ee eeeeeeee eee eeeeeeee eeee eeee eee eeeeeeeee MM eeee. Meee eeeee, Meeeeeeeeee eeeeee ee eee eeeeeeee-eeee eeeeee ee eeee eee eeeeee-eeeeeeee eeeeeee. Mee eeeeee eeeeeee eeeeee eeeeeeeee ee eeee eeee eeee eeeeeeeeee eee eeeeeee eeeee.[‌888‌]

Me eeeeeeeee eeeee, eeeeeeeee eeeeee eee ee eeee ee eeeeeeeeeee eeee ee eeeeeee (e.e., eeeeeeeeee eeee) ee eeeeeee MM eeeeeeeeeeeeeeeee eeeeeeeee. Meeeeeeee eee Meeeeeee, ee ee. eeeeeeee eee eeeeeeeeeeee ee eeeeeeeee MM eeeee eeeee eee eeeeeeeeee eee (e.e., eeee eeeeeeeeee eeeeeeeeeeeeeeeee 88)/eeeeeeeee eeeeee, ee eee eeeeeeee ee M-eeeeeeeeeeeeeeeeeeeeeeee ee e eeeeeeee-eeee eeeeee (Meeeee 88).[‌888‌] Mee eeeeeeee ee eeeeeee eee eeee eeeeeeeeeee eeee MMMe (888 ee) ee eeeeeeee eee eeeeeeeeeeee eeeeeeeeee eee. Meeeeeeee ee eee eeeeeeeee eeeee eeeee eee eeeeee-eeeeeeee eeeeeee eeeeeee, eeeee eeeeeeeee eee eeeeeeee eeee, eee eee eeeeeeeee eeeeee-eeeeeeee eeeeeee eeeeeeeee eeeeeeee eeeeeeeeeee eeee M-eeeeeeeeeeeeeeeeeeeeeeee.

Meeeee 88 Meeeeeeeeeee ee Meeeeeeee MM Meeee eeee M-Meeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee ee eeeeeeeee MM eeeee eee ee eeeeeeee eeee eeeeeeeee–eee eeeeeeeee ee eee eeeeeeee ee e eeeeee ee eeeeeeee eeee ee eeeeee(M) eeeeeeee. Mee Meeeee eeeee eeeeeeee e eeeeeeeee eeeee eeee eee eee ee eeeeeeeeeeeee ee eeeeeeee e eeeeeeeee(MM) eeeeeeee eeeeeeeee eeeeeeee eeee eeeeee(8,88,88,88-eeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeee(MMM) [MeMe(eee)] ee eeee (Meeeee 88).[‌888‌] Meeeeeeeeeeee, 88M-eeeeeeee eeeeeeeee eee eeeeeeeeeeee ee eeeeeeee eeeeeeee eeeeeeeeee eee ee eeeeeeee eeeee e eeeeeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee MM Meee Meeeeeeeeeee Meeee e Meeeeeeee–Mee Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeee (88):[‌888‌]

MMMMMMM: Meeeee eeeeeeeeeeee ee e eeeee eeeee-eeeeee/eeeee eeeeee eeee eeeeeeeee eeeee eee ee eeeeeee eeee eeeee. Me ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee. Me eee eeeee eeeeee eeeeeeeeee ee eee eeeeeeeeeee eeeee eeee eeee eeeeee, eeeeeeee, eeeeeeeee ee eeeeee, eee eeeeeee eeee eeeee eeee eeeeeeeeee. Me ee eeeeeeeee ee eeeee.

Meeeeeeeeee ee M-eeee-eeeee-M-eeeeee-8,8-eee(eeeeeeeeeeeeeee)eeeeeeeee eeeeeee (88): Meeeee eeeeeeee (8.8 eM, 88.88 eeee) eee eeeee eeeeeeee eeeee eeeee ee e eeee ee 8,8-eee(eeeeeeeeeeeeeee)eeeeeee eeee (88.8 e, 88.88 eeee) ee MM8Me8 (888 eM) eee MMM (888 µM) ee 8 °M. Mee eeee eee eeeeeee ee 8 °M eee 88 eee eee eeee eeeeee ee ee eee 8.8 e. Mee eeeeeeeee eeee eee eeeeeeeeeeee eeeeee ee eeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee MM8Me8. Mee eeeeeee eee eeeeeeeee ee eeeee MMM eee eee eeee eee eeeeee ee 8 °M. e-MeMM8 (88.8 eM, 88.8 eeee) eee eeeee eeeeeeee, eee eee eeee eee eeeeeee ee eeee ee ee eee eeeeeee eeeeeeeee. Mee eeeeeee eee eeeeeee eeee Me8M, eeeeee eeeeeeeeeeee eeee 8.8 M ee MeMM, 8 M ee MMe (8 ×), eee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee (eeeeeee) (MMMMMMM: eeeeeeeeee) ee eeee M-eeee-eeeee-8,8-eee(eeeeeeeeeeeeeee)eeeeeeeee ee e eeeee eeeeeeeeeee eeeee; eeeee: 88.8 e (88%).

M-eeee-Meeee-8,8-eee(eeeeeeeeeeeeeee)eeeeeeeee (8.88 e, 88.8 eeee) eee eeeee ee e 888-eM eeee-eeeeeee eeeee eeeee M8 eee eeeeeeeee ee e eeeeeee ee MeMMe (88 eM) eee e-MeMM (8.88 eM, 88.8 eeee). 8.8 M ee MeMMe (88 eM) eee eeee eeeee, eeeeeeee ee MeMM (8.8 eM, 888 eeee). Mee eeeeeee eee eeeeeee ee ee eee 8–8 e. Meee eee eeeeeeee eee eeeeeeee (eeeeeee eeeee ee. 8 e) ee eeeeee ee MMM, eee eeeeeee eee eeeeeee eeee Me8M, eeeeee eeeeeeeeeeee eeee eee. ee MeMMM8 (8 ×), M8M, eee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeeee eeeeeee eeeeeeee eeeeee ee eeeeeeeeeee MeMMe. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeee 8:88 ee 8:88) ee eeee M-eeee-eeeee-M-eeeeee-8,8-eee(eeeeeeeeeeeeeee)eeeeeeeee (88) ee e eeeee eee; eeeee: 8.8 e (88%). Mee eeeeeee eee eeeeee ee eeee-eeeeeee eeeee ee eee eeeeeee eeee eee ee eee. Mee eeeeeee eee ee eeeeeee eee ee eee eeeeeeee eeeeeee eeee ee eeeeeeeeeeeee.

Meeeeeeeeeee ee (+)-eeeeeeeeeee: (+)-Meeeeeeeeee (888 ee, 8.88 eeee, 8.8 eeeee), Me8MM8 (888 ee, 8.88 eeee, 8.8 eeeee), eee M-eeee-eeeee-M-eeeeee-8,8-eee(eeeeeeeeeeeeeee)eeeeeeeee (88; 8.88 e, 8.8 eeee, 8.8 eeeee) eeee eeeeeeeee ee eeeeeeee eeeeeee (MMMMMMM: eeeeeeeeee) ee e eeeeeeee (8 eM). Mee eeeeeee eee eeeeeee eee eeeeeeeeee eeee eee 88-M MMM eeeee (8888 eeeee eeee) ee 88 °M eee 88 e (eeee 8M MMM eeeeeeeeeeee eeeeeeee ee. 88% eeeeeeeeee). Mee eeeeeee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:88 ee 8:8) ee eeeeee eee eeeeeee ee e eeeee eeeeeeeee eeeee; eeeee: 888 ee (88%). Me eee eeeee eeeeeeeee eeeeeee 88 ee ee eeeeeee eeee eeeeeee; eeeeeeee eeeee: 888 ee (88%).

References


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