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37.9.1.1.1 Intramolecular Williamson Etherification of 1,5-Halohydrins

DOI: 10.1055/sos-SD-137-00104

Vashchenko, B. V.; Grygorenko, O. O.Science of Synthesis Knowledge Updates, (20213244.

The base-mediated intramolecular cyclization of 3-chloro-2-(2-hydroxyethoxy)propan-1-ol (11), obtained by the reaction of allyl alcohol (10) with molecular chlorine in ethylene glycol, leads to (1,4-dioxan-2-yl)methanol (12) in 18% yield for two steps. The possible oxetane 13 is not observed (Scheme 2).[‌22‌]

Meeeee 8 Meeeeeeeee 8,8-Meeeeee Meeeeeeee eeee 8-Meeeee-8-(8-eeeeeeeeeeeee)eeeeee-8-ee[‌88‌]

Me eeeeeee, eeeeeeeee ee eee eeeeeeee 8,8-eeeeeeeeeee eeeeee ee eeeeeee eeee eeeeeee. Meee, eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee eeeeeeeee eeee eeeeeee ee eee- eee eeeee-eeeeeeeeeee eeeeeeee 88 eeee 8-eeeeeeeeeeee eeeee eee eeeeeeeeeeeee eeeee- eee eee-eeeeeee eeeeee 88, eeeeeeeeeeee, eeeee eee ee eeee ee eeeeeeeeee eeeeeeeeeeee eeeeeee eeeeeeeeee eeeeeeeeeeee (Meeeee 8).[‌88‌] Mee eeeeeeeeeeeeee ee eeeeeeeee eee eeeeeee ee eeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeee, eee eee eeeeeeeeeeeee 8,8-eee(eeeeeeeeeeeeeee)-8,8-eeeeeeee 88 eee eeeeeeee ee 88 eee 88% eeeee eee eee eeeee- eee eee-eeeeeeeeeee, eeeeeeeeeeee. Meeeeeeeee eeeeeeeeeeeee ee 88 eeeee eeee 88, eee eeeeeeeeee ee 88 eeeeeeee eee(eeeeeeeeeeeeeeeee) 88, eeeee eee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeee 88 eeee eeeeee eeeeeee eeeeeeeeeee (Meeeee 8). Meeeeee, eeeeeeeeeeeeeee ee 88 eeeeeeeee eeee 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee eeeee 8,8-eeeeeeeeeeeeeeeeeeeeee (MMMM, 8) ee 88% eeeee eeee eee eeeee-eeeeee ee 88 ee ee 88% eeeee eeee eee eee-eeeeee, eeeee eeee eeeeeeeee 88 ee 88% eeeee.

Meeeee 8 Meeeeeeeee Meeeeeeeeeeeee ee e 8,8-Meeeeeeeeeee eee Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8

Meeeee Meeeee (%) Mee
88 88 88 88 8
eeeee 88 (8 e) 88 88 (88 e) 88 (88 e) 88e (8 e) [‌88‌]
eee 88 (88 e) 888 88 (88 e) 88 (88 e) 88e (8 e) [‌88‌]

e Meeeeeeee eeeee eee eeeee ee eeeeeeeeeee.

e Meeee ee eeeeeee 8 eeee eeeee-88.

e Meeee ee eeeeeee 8 eeee eee-88.

8,8-Meeeeeeeeeeeeeeeeeeeee (8) ee e eeeeeee eee eee eeeeeeeeeee ee eeee(8,8-eeeeeeeeeeeeeeeeeeeeee) (MMMMM, 88), e eeeeee eeeeeeeeee eeeeeee eee eeeeeeee eeeeeee.[‌88‌‌88‌] Meeeeeeee ee MMMMM eeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeee (8) eeee eeee(MMM) eeeeeeee ee ee eeeeeeeee eeeee ee eee eeeeeeeeeeeeeeeeeeeee. Meeeeeeeee ee MMMMM eeeeeee eeeeeee eeeeeeeeeeee ee eee eeeeeeeeee eeeee, eeee eeeeeeeee, eee eeeeeeee eeee eee eeee eee eeeee eeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeee ee eeeeee 88 eeee 8-[(8-eeeeeeeeeeee)eeeeee]eeeeeee (88) eeeee ee eeeeeeeee ee 8,8-eeeeeeeeeeeee 88, eee eeeeeeee ee eeeeeee eeee eeeeeee eeeeeee ee eeeeeeee eeeeeeeeeeee eeeeeeeeeeee (Meeeee 8).[‌88‌] Meeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee ee 8-(8-eeeeeeeeeeee)eeeeee-8-eee 88 eeeeeeee eeeeeeee eeee eeeeeee eeee eeeeee eeeeeeeee ee 8,8-eeeeeee eee eeeee 8-eeeeeeeeeee 8,8-eeeeeee eeeeeeeeeee 88.

Meeeee 8 Meeeeeeeeee ee M-[(8,8-Meeeee-8-ee)eeeeee] Meeeee[‌88‌]

Meeeeeeeeee 8

M8 Meeee ee 88 (%) Meeee ee 88 (%) Mee
eMe 88 88 [‌88‌]
Me 88 88 [‌88‌]

Meeeeeeee ee eeeee-eeeeeeeee-8M-[8,8]eeeeeee[8,8-e]eeeeeee 88 eeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee eeeeeeee eeeeeee eeee eeeeeee ee 8-eee-8-eeeeeeeeee[8.8.8]eeeeee 88 eeee 8-eeeeeeeeeeee, eeeee eeeeeee ee 8,8-eeeeeeeeeee 88 ee 88% eeeee (Meeeee 8).[‌88‌] Meeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee eeee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeee eeeee eeeee 8,8-eeeeeee eeeeeeeeee 88 ee 88% eeeee, eeeee eee ee eeee ee e eeeeeeee eeeee eee eee eeeeeeeeeee ee eeeeee eeeeeeeeee ee eeeeeeeeeeeeeeeeeeee 8-eeeeee (MM8Me).

Meeeee 8 Meeeeeeeee Meeeeeee eee Meeeeeeee ee Meeeee eeeee-Meeeeeeee-8M-[8,8]eeeeeee[8,8-e]eeeeeee-8-eeeeeeeeeee[‌88‌]

Meeeeeeee ee eeeeeeeeeeee 8,8-eeeeeeeeeeeee 8,8-eeeeeee 88 eeeeeeeee eeee eee eeeeeeee ee eeeeee eeeeeee eeee (M)-8-(eeeeeeeeeeee)eeeeeee ee eee eeeeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee 8,8-eeeeeeeeeeeeee (Meeeee 8).[‌88‌] (M)-8-(Meeeeeeee)-8-eeeeeeeeeeee-8-ee (88) eeee eeeeeeee eeeeee eeee (M)-eeeeeeee 8-eeeeeeeeeeeeeeee (88) eeeee eee eeeeeeeeeeeeee eeeeeeeeee, eee eee eeeeeeeeeeeee 8,8-eeeeeeeeeeee 88 ee eeeeeeee ee 88% eeeee. Mee eeeeeeeeee 8-eee-eee eeeeeeeeeee ee 88 eeeeeeee eeeee eeeeee eeeeeeeeee (ee MeMM, 88°M) eee eeeeeeeee {(8M,8M)-8-[(eeeeeeeee)eeeeee]-8,8-eeeeee-8-ee}eeeeeeee (88) ee 88% eeeee.

Meeeee 8 Meeeeeeee ee {(8M,8M)-8-[(Meeeeeeee)eeeeee]-8,8-eeeeee-8-ee}eeeeeeee[‌88‌]

Meeeeee eeeeeee ee eeeeeee eeee eeeeeee eeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee eeeeeeee eeeeeeee ee eeeeeee 88 eeee 8-eeeeeeeeeeee ee eeeeeeeeeeeeeee, eeeee eeeee eeeee eeeeeee 88 ee 88% eeeee (Meeeee 8).[‌88‌] Meeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee ee 88 ee eeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeee/eeeee eee eeeeeee eee eeeeeeeeeeeee 8,8-eeeeeee 88 ee 88% eeeee.

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

Meeeeeeeeee ee 8-(eeeeeeeeeee)-8,8-eeeeeeee 88 eeeeee ee eee eeeeeeeeeee ee eeeeeeeee [8-(8-eeeeeeeeeeee)-8-eeeeeeeeeeeee]eeeeeeeeee 88, eeeee eeeeeeee eeeeeeee ee eeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee (Meeeee 8).[‌88‌] Meee eeee eeeee ee 8,8-eeeeeee-eeeeeee eeeeeeeeee 88 ee eeeeee eeeeeeeeeeee eeeeee, eee eeeee eeeeeeeeee eeeeeeeeeee eeeeeee ee 8-(eeeeeeeeeee)-8,8-eeeeeeee 88 ee 88–88% eeeee. Meeeee eeeeeeeeeeeeee ee eeeeeeeee [8-(8-eeeeeeeeeeee)-8-eeeeeeeeeeeee]eeeeeeeeee 88 eeee 8-(eeeeeeeeeee)-8,8-eeeeeeee 88 eeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeee ee eeeeeee ee e eeeeee eeee ee 888°M. Meeee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeee eeeee ee eeeeeeeee ee eee eeeeeeeeeeeee eeeee eeeeee.

Meeeee 8 Meeeeeeeee Meeeeeeee ee 8-(Meeeeeeeeee)-8,8-eeeeeeee[‌88‌]

Meeeeeeeeee 8

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

e Meeeeeeeee ee 8M MMM eeeeeeeeeeee.

e Meeeeeee eeeee.

Me eee eeee ee 8,8-eeeeeeeeeeeeeee-eeeeeeeeeee eeeeeeeeee 88, eee eeeeeeee eeee eeeeeeeee eeeeeeeee ee eeeeeee eeeee ee eeeee eeeee 88 eeeeeee ee eee eeeeee 8,8-eeeeeee 88 (Meeeee 88).[‌88‌] Meeeeeeee ee eee eeee (MMMM8, M8MM8, ee Me8M) eeeeeee eeee ee e eeeeee ee eee eeeeeeee eeee eee eeee eee eeeee eee eee eeeeeeeeeee ee 88.

Meeeee 88 Meeeeeeee Meeeeeeeeee ee Meeeeeeee [8-(8,8-Meeeeeeeeeeeeee)-8-eeeeeeeeeeeee](eeeeee)eeeeeeeee[‌88‌]

Meeeeee, eee eeeeeeee 8,8-eeeeeeeeeeeeee-8-ee eeeeeeeeeee eeeeeeeeee 88 ee e eeeeeeee eeeeeeee eeeeeeee eee eee eeeeeeeeeee ee 8,8-eeeeeeee (Meeeee 88).[‌88‌] Meeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeee ee eee eeeeeeeeeeee 8-(eeeeeeeeeeee)eeeeeeee 88 eeee eeeeeeee eeee eeeeeeeeeee ee eeeeeeeeee eeeee ee 8,8-eee(eeeeeeeeeee)eeeeeeee 88 ee 88 eee 88% eeeee, eeeeeeeeeeee. Meeeeee, eee eeeeeeeeeeee eeeeeeeeeeee eeee ee eee eeeeeeee, eee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeeeeee eee eeee eeeeeeee ee eeeeeeeeee.

Meeeee 88 Meeeeeeee ee 8,8-Mee(eeeeeeeeeee)eeeeeeee[‌88‌]

Meeeeeeeeee 88

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

Meeeeeeee ee eeeee β-e-eeeeeeeeeeeeeee 88 ee eeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeee 88 ee eee eeeeeeee ee eeeeeeeee eeee-eeeeeeee ee eeee-eeeee eeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee e Meeee β-e-Meeeeeeeeeeeeee[‌88‌]

Mee eeeeeeeeeeeeee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee 88, eeeeeeee eeee e-eeeeeeee ee eeeeeeeee eeee 8-eeeeeeeeeeeee eee eeeeee eeeeeeee, eeeeeeee eeee eeeeeee eeeee ee eeeeeee eeeeeeee ee eeee eeeeeeeeeee 8,8-eeeeeee 88 ee 88–88% eeeee (Meeeee 88).[‌88‌‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-M-Meeeeeee-β-e-eeeeeeeeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

Meeeeeeeee Meeee (%) Mee
8. MeMMe, MeMM, eeeeee, 88 eee
8. Meeeeeeee MM-888 (M+) eeeee
8. eeeeeeeee eeeeee Meeee M
88 [‌88‌]
8. 8 M MeMM ee MeMM, eeeeee, 88–88 eee
8. Meeeeeeee MM-888 (M+)
88 [‌88‌]
8. 8.8 M MMM ee MeMM, eeeeee, 88 eee
8. Meeeeeeee MM-888 (M+)
8. Meeeeeeee MMM-888 (MM)
88 [‌88‌]

Me eee eeeee eeee, eeeeeeeee ee (8M,8M)-8-(eeeeeeeeeeee)-8-(eeeeee-8-ee)-8,8-eeeeeee (88) eeee eeeeeeeeeeeeee 88 ee eeeeeeeeeee ee eeeeeeeeeee eeeeeeeee ee eee M-eeeeeeeee eeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee (8M,8M)-8-(Meeeeeeeeeee)-8-(eeeeee-8-ee)-8,8-eeeeeee[‌88‌]

Mee Meeeeeeeee eeeeeeeeeeeeee ee eeeeee eeeeeeeeeeee 88 eeeee eeeee eeeeeeeeee eeeeeeee eeeeeee eeeeeeeeeeee. Meeeeeeeeeee 88 ee eeeeeeee ee 88% eeeee ee >88:8 eeeeeee ee eeeeeeeeeeeee ee Meeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeee eeeeee 88 (88% ee); eeeeeeeeee eeeeeeeeeee ee 88 eeeee ee 8,8-eeeeeee 88 ee eeeeeeeee eeeee eeee 88% eeeeeeeeeeee eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeeee Meeeeeeeeeeeee[‌88‌]

Mee eeeeeeeeeee ee eeee 88, ee eeeeeeeeeeee eee eee eeeeeeeee ee 8,8-eeeeeee eeeeeeeeee 88, ee eeeeeeeeeee ee eeeeeeeeeeee ee eee α-eeeeeee eeeeeeee 88 eeeeeee ee M8-eeeeeeeee 8,8-eeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌] Me eeeeee eee eeeeee eeee eeeeeee 88 (88% eeeee), eeeeeeeee eeeeeeeee ee α-eeeeeee eeeeeeee 88 eeee eeeeee eeeeeeeeeee ee eeeeeee ee eeeeeeee. Meee 88 ee eeee eeeeeeeeeee eeee eeeeeee eeeeee 88 eee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeee eee eeeeeee eeeeeee eeeee eee eee ee eee eeeeee eeeeee ee 8-eeeee-8,8-eeeeeeeeeeeeee. Meee eeeee 88 ee 88% eeeee; eeee eeeeeeeee ee e 8,8-eeeeeeeee eeeeeeeeee ee eeee eeeeeeee (88% eeeee). Meeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeee 88 ee eeeeeeeee eeee 8% eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee. Meeee eeeeee eeeeeeeeee eeee 8 M eeeeeeeeeeee eeee ee eeeeeee ee eeeeee eeeee 8,8-eeeeeee eeeeeeeeee 88 ee 88% eeeee.

Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee Meeeeeeeee eeee e 8-(8-Meeee-8-eeeeeeeeeeee)eeeeeee[‌88‌]

Me eeeeeeeeeee eeeee eeee 8,8-eeeeeeeeeee eeeeee ee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeee eee eeeeee 88 ee eee eeeeeeee ee eeeeee eeee eeeeeeee 88, eeeee eeeeeeeee eee eeeeeeeeeeeee eeeeee eeeeeeee 88 ee eeee eeeeee eee eeeeeeeeeeeeeeeeeeee eeeee eeeeee ee eeeeee eee (Meeeee 88).[‌88‌] Meeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeee eeee eeeeeeeee eeee-eeeeeeee ee eeeeeeeeeeeeeee eee eeeee ee eee eeeeeeeee ee 8,8-eeeeeeee 88. Meeeeeeeeeeee, eeeeee ee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eee eeeeee 88 eeee eeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeeeeee ee 8,8-eeeeeeee 88 ee e eeeeee eee ee eeee eeeeee.

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee ee Meeeee Mee Meeeee[‌88‌]

Meeeeeeeeee 88

M8 ee (%) Meeee (%) Mee
88 88 88 88
8-MM8M8 88 88 88 88 [‌88‌]
88 88 88 88 [‌88‌]
8-eeeeeee 88 88 88 88 [‌88‌]

Mee eeeeeeeeeeeeeee eeeeeeeeee eeeee-eeeee eeeeeeee eeeeeee 8-eeeeeeeeeeeeeeeee eee 8-(8-eeeeeeeeeeee)eeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee (M)-eeeeeeee(eeeeeeeeee-8-ee)eeeeeeee (88) ee eeeeeeee ee eeeeeeeeeeeeeeeee; eee eeeeeeee eeeeeeee eee 8 eeee eee eeeee (8M,8M)-8-(8-eeeeeeeeeeee)-8-(8-eeeeeeeeeee)eeeeeee-8,8-eeee (88) ee 88% eeeee (ee 8:8, 88% ee; Meeeee 88).[‌88‌] Me eee eeee ee eeeeeeeeeeee/eeeee ee eee eeeeeee eeeeee, eeeeeee 88 ee eeeeeeee ee eeee eeeeee eeeee (88% eeeee, 88% ee) eee eeeee eeeeeeeeeeeeee eeeee (8.8:8) eeeee 8 eeee. Meeeeeeee eeeeeeeeeee ee eeeeeeeeeeee 88 eeee eeeeeeeee eeee eeeeee eeeeeee ee eeeeeeeee eeee-eeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee ee 8°M ee eeee eeeeeeeeeee eeeee ee eeeeeeeee ee eeeeeee eeeeeeee. Meee eeeeeeeee eeee-eeeeeeee ee eeeeeeeeeeee ee eeee, 8,8-eeeeeee 88 ee eeeeeeee ee eee eeeee eeeeeeeeeeee ee 88% eeeee (88% ee) eeeee eeee e eeeeeee eeeeee (ee. 88%) ee ee eeeeeeeeeee eeeeeee ee eeeeeee.

Meeeee 88 Meeeeeeeee Meeeeeeeeeeeee ee e Meeeee Meee[‌88‌]

Meeeeeeeeee 88

Meeeeee ee ee (%) Meeee (%) ee 88 Mee
MMM 8:8 88 88 [‌88‌]
MeMM/M8M 8.8:8 88 88 [‌88‌]

Mee eeee eeeeeeee ee (8-eeeeeeeeee)eeeeeeee eeeeee ee eeeeeeeeeeeeeeeee ee eeeeeee 88 eeee eeeeeeeee eeeeeee eee M-eeeeeeeeeeeeeeee (88–88% eeeee), eeeeeeee ee Meeeeeee eeeeeeee ee eeeeeeeeee 88 eeee eeeeeeee (Meeeee 88).[‌88‌] Meeee eeeee eeee eee eeeeeeeeeeeee eeeeeee 88 (eeee ee 88% eeeee). Mee Meeeeeee eeeeeeee eee ee eeeeeeeeeeee eeeeeee ee eeeeeee 88 eee eee eeeeeeeee ee eee eeeeeeee (8-eeeeeeeeeee)eeeeeee eeeeeeeeeeeee 88, eeeee eee eeee eeeeeeeee ee e eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeeeeeeeeeee ee eeeeeeeee eeeeeee eeeee, eeeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee 8,8-eeeeeeee 88 ee 88–88% eeeee. M eee-eee eeeeeeeee eee eee eeeeeeeee ee 8,8-eeeeeeee 88 eeeeeeee eeeeeeee ee eeeeeee 88 eeee eee Meeeeeee eeeeeee ee eeeeeee; eeeeeee, eee eeeeeeee eee eeeeeeee ee eeeee eeeeee (88–88% eeeee).

Meeeee 88 Meeeeeeeeee ee Meeeeeeeeeeeeeee 8,8-Meeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
88 88 88 88
Me M MM8MMM 88 88 88 88 [‌88‌]
Me M Me 88 88 88 88 [‌88‌]
Me Me MM8MMM 88 88 88 88 [‌88‌]
Me Me Me 88 88 88 88 [‌88‌]

Meeeee eeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeee 88 eeee eee eeeeeee ee eeeee eeeeee (MM8-eeeeeeeee eeeeeeeeee); eeeeeee, eeee eeeeeeeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeee 88.[‌88‌] Me eeee, eeeeeeee eeeeeeeeee eee MM8 eeeeeeeeeeee [eeeeeee ee eee eeeeeeee ee eeeeee(M) eeeee ee eeeee ee eeeeeeee eeeeeeeee ee 88°M, Meeeee 88] eee eeee eeeeeeeeeeee. Meeeeeeeee eee eeeeeeee eeeeeeeeeee ee 888°M eeeee 8,8-eeeeeee 88 ee 88% eeeee; eee eeeeeeeeeeeee eeeeee 88 ee eeee eeeeeeee ee e eeeee eeeeeee (88% eeeee). Meeeeeee ee eeeeeeee (8 eeeee) eeeeee eee eeeeeeeeeeeeee ee eeeeeeee eeeeee eeeeee eeeeee eee eeeeee ee eee eeeeeeee eee eeeeeeeee eee eeeee ee 88 ee 88%. Me eeeeeee ee eeeee eee eeeeeeee eeeeeeeeeee ee eeeeeeee ee eeeeeeeee eeeeee eee eee eeeeeeeee: 88 ee eeeeeeee ee eeeee eeeeeee (88% eeeee) eee eee eeeeeeeeeeeee eeeeee 88 ee eeeeee ee 88% eeeee. Mee eeee eeeeeee eee eeeeeeee eeeee eeee eeeeeeeeee ee 8,8-eeeeeeeeeeeeeeee ee eeeeeeeeeeee (88% eeeee; ee 8:8) ee M-eeeeeeeeeeeeeeee ee eeeeeeeeeeee (88% eeeee; ee 88:8).

Meeeee 88 Meeeeeee Meeeeeeeee eee Meeeeeeeee Meeeeeeeeee ee Meeeeee Meeeeeeeeee[‌88‌]

Meeeeeeeeee 88

Meeee Meeeeeeeee Meeee (%) ee 88 Mee
8 Me8M, eeeee, 88°M, 88 e 8 [‌88‌]
8 MMMM, 88°M, 8 e 8 [‌88‌]
8 MMMM, 888°M, 8 e 88 (88)e [‌88‌]
8 eeeeeeee (8 eeeee), MMMM, 888°M, 8 e 88 (88)e [‌88‌]
8 eeeeeeee (8 eeeee), M8 (8 eeeee), MMMM, 88°M 88 (88)e [‌88‌]
8 M8 (8 eeeee), MeMM, 88°M 8 [‌88‌]
8 8,8-eeeeeeeeeeeeeeee (8.8 eeeee), MeMM, ee 88 (ee 8:8) [‌88‌]
8 MMM (8 eeeee), MeMM, ee 88 (ee 88:8) [‌88‌]

e Meeee ee eee eeeeeeeee 88 ee eeeeeeeeeee.

Meeeeeee ee eee 8,8-eeee eeeeee ee eee eeeeeeee ee 8-eeeeee-8-eeeeeeeeeeeeee (88) eeee eeeeee eeeeeeeee eeeeeeee ee eeeeee eeeeeeeeeee eeeeeeee eeeeeeeee eeeee eeeeee eeee 88 ee 88% eeeee. Meeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee eeeee eeeee eeeeeeeeee eeeee eeeeee eeeeeeeee ee eeeeeeeeeeeeeeeee eeeee 8,8-eeeeeee-eeeeeeeeee eeeeeee eeeeeeeeee 88 ee 88% eeeee (Meeeee 88). Me eeee eeee, e eeeeeeeeeeeee eeee eee ee eeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee e 8-(8,8-Meeeee-8-ee)eeeeeee Meeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

eeeee-8,8-Mee(eeeeeeeeeeeeeee)-8,8-eeeeeee (eeeee-88):[‌88‌]

M 8 M eeee ee MM8MMe8 ee MM8Me8 (8.88 eM, 8.88 eeee) eee eeeee ee e eeeeeee ee eee-8,8-eee[(eeeeeeeee)eeeeee]eeeeeee (88; 88 ee, 8.88 eeee) eee 8-eeeeeeeeeeee (88 ee, 8.88 eeee) ee ee. Mee eeeeeee eee eeeeeee ee ee eee 88 e eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. M eeee ee MMM (88 ee, 8.88 eeee) ee MeMM (8 eM) eee eeeee ee eee eeeeeee ee MeMM (8 eM) ee e eeeee-eeeeeeee eeeee ee ee. Mee eeeeeee eee eeeeee ee eeeeee eee 8 e, eeee eeeeee ee ee, eee eeeeeeee eeeeeee e eee ee Meeeee. Mee Meeeee eee eee eee eeeee-eeeeeeee eeeee eeee eeeeee eeee MeMMe. Mee eeeeeeee eeee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, eeeeee/MeMMe 8:8); eeeee: 88%.

eee-8,8-Mee(eeeeeeeeeeeeeee)-8,8-eeeeeee (eee-88):[‌88‌]

M 8 M eeee ee MM8MMe8 ee MM8Me8 (8.88 eM, 8.88 eeee) eee eeeee ee e eeeeeee ee eeeee-8,8-eee[(eeeeeeeee)eeeeee]eeeeeee (88; 88 ee, 8.88 eeee) eee 8-eeeeeeeeeeee (88 ee, 8.88 eeee) ee ee. Mee eeeeeee eee eeeeeee ee ee eee 88 e eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. M eeee ee MMM (88 ee, 8.88 eeee) ee MeMM (8 eM) eee eeeee ee eee eeeeeee ee MeMM (8 eM) ee e eeeee-eeeeeeee eeeee ee ee. Mee eeeeeee eee eeeeee ee eeeeee eee 88 e, eeee eeeeee ee ee, eee eeeeeeee eeeeeee e eee ee Meeeee. Mee Meeeee eee eee eee eeeee-eeeeeeee eeeee eeee eeeeee eeee MeMMe. Mee eeeeeeee eeee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, eeeeee/MeMMe 8:8); eeeee: 88%.

M-[(8,8-Meeeee-8-ee)eeeeee] Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee ee M-[8-(8-eeeeeeeeeeee)-8-eeeeeeeeeeeee) eeeee 88 (8.88 eee) eee MeMM (88 e, 8.8 eee) ee 8,8-eeeeeee (88 eM) eee eeeeeee ee 88°M eee 8 e. Mee eeeeeee eeeee eee eeeeeeeee eeee eeeeeeeeeeee eeeee, eeeeee eeee M8M (8 × 88 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.

8-[8-(Meeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeee-8-ee (88):[‌88‌]

M eeee ee 8-(eeeeeeeee)-8-(8-eeeee-8-eeeeeeeeeeee)-8-eeeeeeeeeeee-8-ee (88; 88.8 e, 88 eeee) ee 8% eeeeeeeeee MMM (888 eM) eee eeeeee ee eeeeee eee 8 e eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee Me8M, eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (MM8Me8) ee eeee eee eeeeeeee eeeeee ee ee eee; eeeee: 8.8 e (88%). Mee eee (8.8 e, 88.8 eeee) eee eeeeeeeee ee eeeeeee (88 eM). 8 M ee MMe (88.8 eM) eee eeeee eee eee eeeeeee eeeeeee eee eeeeee ee eeeeee eee 8 e, eeeeee ee 88°M, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeee eeeeeee eee eeeeeeeee ee Me8M, eeeeee eeee eee. ee MeMMM8, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (MM8Me8/Me8M 88:8); eeeee: 8.88 e (88%).

8,8,8,8-Meeeeeeeeeeeeeee 8,8-Meeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeee eeeeeee 88 (8.88 eee) eee eeeee ee e eeeeeee eeeeeeeeee ee MMM (8.88 e) ee Me8M (88 eM). Mee eeeeeee eee eeeeee ee eeeeee eee 8 e eee eeee eeeeeee eeee M8M. Mee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.

8,8,8,8-Meeeeeeeeeeeeeee 8,8-Meeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeee eeeeee 88 (8.88 eee) eee eeeeeeeee eeeee ee e eeeeeee Meeeeeee eeeeeee eeeeeeee eeee eeeeeeeee eeeeeee (8.8 e) eee Me (8.8 e) ee eeeeeee (88 eM) eeeeee ee 8°M. Mee eeeeeee eeeeeee eee eeeeee ee 88–88°M eee 8 e, eeee eeeeee ee ee, eeeeeee eeee M8M, eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.

References


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