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40.1.5.1.4.2 Variation 2: Cyclization of 2-Aminoalkanols

DOI: 10.1055/sos-SD-040-00445

Sweeney, J. B.Science of Synthesis, (200940691.

Aziridine ring syntheses reported in the contemporary literature often employ cyclization reactions of 2-aminoalkanols; the method was first reported by reported by Gabriel, in 1888. Thus, aziridines were prepared in a two-step process, by chlorination of ethanolamines with thionyl chloride followed by alkali-induced cyclization.[‌268‌,‌269‌] An alternative procedure was developed by Wenker,[‌270‌] who converted ethanolamine into aziridine (ethylene imine) via β-aminoethyl sulfuric acid,[‌271‌] presumably via the cyclic sulfamidate (Wenker himself suggested an oxidized intermediate) (Scheme 101). The process is robust and can be carried out on large scale.[‌272‌] Though the Wenker method remains a useful process for relatively insensitive 2-aminoalkanols, other substrates (such as tertiary alcohols) decompose rather than undergo cyclization. The high temperatures required in the original methods can be avoided using high pressure methods.[‌273‌‌275‌] The reaction is stereospecific: if enantiomerically pure 2-aminoalkanols are utilized, enantiopure aziridines are usually obtained, via SN2 reaction with concomitant inversion (Scheme 101).[‌276‌]

Meeeee 888 Meeeee Meeeeeeee Meeeeeeee[‌888‌,‌888‌]

M eeeee ee eeeeeeeeeeeeeeee eeee 8-eeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee, ee eeeeeeee eeeeee ee eeeeeeeee ee eee eeeeeeeeeeeee eeeee eeee, ee eeee eee eeeeeeeeeee ee eeeeeeeeee eeeeeeeeee ee eeeeeeeeeeeeeee.[‌888‌‌888‌] Meeeeeeeee ee eee eeeeeee ee eeeee eeeeeee eee ee eeeeeeeeeeeee, ee eeee eeeeeeeee eee eeeeeeeee eeeeeeeeeeeee eee eeeee eeeeeeee ee eeeeeeee Meeeee eeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee ee Meeeeeeeeee ee e 8-Meeeeeeeeeeeee[‌888‌]

Meeee eeeee ee eeeeeeeeeeee eeeeeeeeee ee eeeeeeeee eee eeeeeeeeeeee 8-eeeeeeeeeeeee (e.e., eeeeeee ee eeeeeeeee ee eeeee-eeeeeee eeeee eeeeeeeee), eee eeeeeeeee ee M-eeeee eeeee eeeee eeeeee eee eeeeeeeee ee eeeeeeeeeee 8-eeeeeeeeeeeeeee ee e eee-eee eeeeeeee.[‌888‌]

Meeeeee eee eeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeee, eeeeeee eeeeeeee eeeeeeee 888 eeeeeee eeeeeeeee eeeeeee eeeeeeeeee eeee (eeeee)eeeeee eeeeeee eeeeeee 888 (eeeeee ee eeeeeeee ee eeeeeee 888 eeee eeeeee eeee) ee eeee eeeeeeeeeeeeeeee eeeeeeee 8-(8-eeeeeeeeeeeeeeeeeee)eeeeeeeeee 888 eeee eeee eeeeeeeeeeee eeeeee. Meee eeee eee eeeeeeeee eeeeeeee eee eeeeeeeee eeee eeeeeeeeee ee e eeee-eeee eeeeeee eee eeeee eeeeeeee 888, ee eeee eeeeeee eeeee eeee eeeeeee eeeeeeeeeeeeeee eeeeeeeeeeee.[‌888‌] M eeee eeeee ee eeeeeeee, eeeeeee eeeeeeeeeee, eeeeeeeeeee, eee eeee eeeeeeeeeeee, eeeeeee eee eeeeeeee eee eee eeeeeee ee eeeeeeeee eeeeee eeeeeeeeeeeeeeee (Meeeee 888).

Meeeee 888 Meeeeeeeeeeeeeee Meee Meeeeeeeee eee Meeeeee Meeeeeee[‌888‌]

Meeeeeeeeee 888

M8 ee (%) ee 888 Meeee (%) ee 888 Mee
Me >88 88 [‌888‌]
e-Me 88.8 88 [‌888‌]
MM8Me >88 88 [‌888‌]
MM8Me >88 88 [‌888‌]
MM=MM8 >88 88 [‌888‌]
Me 88.8 88 [‌888‌]
Me >88 88 [‌888‌]

Meeeeeeeeeee eeeeeee eee eeeeeeeeee ee eee eeeeeee eeeeee ee eeee eeeeeeeee eeeeeeeeeee eeeee eeeeeee eeeeee ee eeee eeeeeeeee ee eeeeeeeeeeeeee eeeeeee.[‌888‌‌888‌] Meee, eeeeeeee ee 8-eeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeee,[‌888‌] eeeeee eeeeeeeeeeeee,[‌888‌‌888‌] ee eeeeeee eeeeeeeeeeeeeeee eeeee eeeeeeeeee ee eeee eeeeee; eeeee eeeeeee 888, eee eeeeeee, eeeeeee eeeeeeeee 888 (Meeeee 888).[‌888‌] Meeeeeeeeeeeeeeeee eeeeeeee[‌888‌] eee eeeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM),[‌888‌] eeee eeee eeee eeeeeeee ee eeee eeeeee ee eeeeeeeee eeeeeeeee. Meeeeee eeeeeeee eeeeeee eee eeeeeeeee ee 8-eeeee-8-eeeeeeeeeeeeee 888, eeeeeeee eeee eeeee eeeeeeee 888, eeee eeeeeeeeeeeeeeeeee eee eeeeeee eeeeeeeeeeeeeeee, ee eeeeee eeeeeeeeeeeeeeee 888,[‌888‌] eee eee eee-eee eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeeee eeee eeeeeeeeeeee 888 ee eeee M-(eeeeeeeeeeeeeeeeee)-eeeeeeeee eeeeeeeee 888.[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee eeee 8-Meeeeeeeeeeee eee Meeeeeeeeeeeee Meeeeee[‌888‌,‌888‌,‌888‌]

Meeeeee ee eee eeeeeeeee eee eeeeeeeee ee eeeeeeee eeeee eeeee (ee eeee eeeeeee), eeeeee eeeee ee eeeeee eeeeeeeee-8-eeeeeeeeeeee ee ee eeeee eeeeeeeeeeee. Meeeeeee eeeeeeee eee eeeee ee eeee eeeeeeeeee eeee 8-eeeeeeeeeeeee ee eee eeeee,[‌888‌] eee eee eeeeeee eee eee eeeeee eeee eeeee eee eeeeee eeee eeeeee 8-eeeeeeeeeeeeeee-8-eeeeeeeeeeee 888 eeeee ee eeeeeeee ee eeeeeeeee ee eeeeee ee eeeeeeeee eeeeeeeeeee 888 eeee eeeeeeee eeeeeeee ee 88°M; eeee eeeeeeeee eeeeeee eee eee eeeeee eeeeeeeeeee (Meeeee 888).[‌888‌] Meeeee e eeeee eeeeeeeeeee ee eeeeeeee eee e eeeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeeeeee eeeee eee eeeeeee, eeee 8-eee eeeeeeeeeee eeee eee eeeee.

Meeeee 888 Meeeee Meeeeeeee ee Meeeeeeee-8-eeeeeeeeeeee eeee Meeeee eee Meeeeeeee[‌888‌]

Meeeeeeeeeeeeeeeeeeeeeeeeeee (MMMM) eeeeeeee 8-eeeeeeeeeeeee eeee eeeeeeeeee eeeeeeee, eee eee eeeeee eee ee eeeeeeee eee eee eeeeeeeeeee ee eeeeeeeeee eeeeeeeee-8-eeeeeeeeeeee (Meeeee 888).[‌888‌,‌888‌] Meeeeeeee eeeee eeeeeeeeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeeeee (eee eeeeee ee eeeeeeeeeee eee eeeeeeee), eee eee eeeeeee eee eeee eeeeeeee ee ee eeeeeeee, eee eee eeeeeeee eeeeee e eeeeeeeeee ee eee eeeeeeee eeeeeee eeeeeeeee eee eeeeeeeee ee eeeeeeeeeee eeeeeeeee-8-eeeeeeeeee eeee eeeeee.[‌888‌,‌888‌] Mee eeeeeeeee-8-eeeeeeeeee eeeee eeee eeeeeeee eeee eeeeee eeeeee eeeeeeeee eeeeeeeeeeeee eee eee eeeeeeeee ee (8M)-eeeeeeeee-8-eeeeeeeeee eeee eeeeeeeeee eeeeeeee.[‌888‌]

Meeeee 888 Meeeeeee Meeeeeeee ee Meeeeeeeee Meeeeeeee-8-eeeeeeeeeeee Meeee Meeeeeeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeee 8-eeeee eeeeeeeee eee ee eeeeeeee ee eeeeeeeeee.[‌888‌] Meee eeeeee ee eee eeeeeee eee eee eeeeeeeee ee 8-eeeeeeeeeeeeee, eeeee eeeeeeeeee eeeee eeeeeeee e eeeeeeeee eeeeeeeeeeee eeeeee ee eee eeeeeeee eeeee, eeeeee eeeeeeeeeeeeeee ee eeeeeeeeeee eeeeeeee, eeeeee eeee eee eeeeeeeee. Meee, eeeeeee eee-eeeeee eeeee 888 eeeee eeeeeeeee 888 eeee eeeeeeeee eeee eeee, eee eeee-eeeeee eeeeee eeeee eee eeee eeeeeeeeee ee eeee e eeeeeeeeeeeeee (Meeeee 888). Meeeeeeeee eeee eeee eeeeeeeeeeeeeee eeeee eeeeeee eeeeeeeeee,[‌888‌] eee eeeeeeeeee eeeeeeeee eeeeeeeee eeeee eeeee eeeeeeeeee eee eeee.[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee ee Meeeeeeeeee ee 8-Meeeee Meeeee[‌888‌]

Meee eeeeeeeeeeee eee eeeeee eee eeeeee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeee eeeeeeeee eeeeeeeeee, eee eeeeeee 8-(eeee-eeeeeeeeeeeeee)eeeeeeeeee, eeee 8-eeeeeeeeeeeee eeeeee eeeeeee, eeeee eeeeeeeee e eeeeeeeee eeeee eeeeeeeeee. Me eeeeeeeeee, eee eeeeeeeeeee ee 8-eeeeeeeeeeeeeeeee eeee 8-eeeeeeeeeeeee ee eeeeeeeeeee, eeee eee eeeeee eeeeeeeeee eeeee eeeee eeee ee eeeeeeeeee eeeeeeeee eeeeeeeee.[‌888‌] Meee, M-eeeeee-8-eeeeeeeeeeeee eeee eeeeeeeeee eeeeeeeee eeee 8-eeeeeeeeeeeeeee eeeeeeee, eeeeeeee, eee eeeeeeeeeeeee eeeee 8-eeeeeeeeeeeeeeee, eeeee eee eeeeeeeee eeeeeeeeeee eeeee eeeeee eeeeeeeeee eee eeee eeeeeeeeeee ee eeee eeee eee eeeeeeee eeeeeeeeeeeee.

Meeeeeeee eee eeeeeee eeeeeeeee ee M-eeee-8-eeeeeeeeeeeee eee eeee eeeee eeeeeee ee eeee eeee eeeeeeeee, eee eeee eeeeeeeeeee eeeee eeeeeeee ee e eeeeeeeeee eeee eeeeeeee.[‌888‌] Meeeeee, ee eeeee eeeeeeeee, eee eeeeeeeeeee eeeeeee eee eeeee e eeeeeeee eeeeeeeee eeee eee eeeeeee ee eeeeeee ee eee eeeeeeeeeeeeee. Meee, eee eeeeeeeee ee M-(eeeeeeeeeeeeeeeee)-M-eeeeee 888 eeeeeeee ee eeee e β-eeeeee, eee eee eeeeeeeee eeeeeeeee eeeeeeeeee 888 eeeee ee eeeeeeeee ee eee eeee eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee ee 8-Meeee-8-(eeeeeeeeeeeee) Meeeee[‌888‌]

Mee eeeeeeeee ee eee eeeeeeeeeeeeeeeeee eeee eeeeeeeee ee eeee eeeeeee: eeeeeeeee-eeeeeeeeee eeeeeeee eeeeeee ee eeee eeeeeeeeee eeeeeeee, eeeeeee eeee-eeeeeeeee eeeeeeeeeee eeeee eeee eeeeeeeeeeeeeee eeee eeeeeeee eeee eeeeeeeeeeeeeeeeee/eeeeeeeeeee eeeeeeeeeeeeeeee (MMMM) (Meeeee 888); eeeeeeee eeee eeeee eeeeeeeeee eeeeee eeeee eeeeeeeeeeeeee eeeeeeee eeeeeeeeeee.[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeeee Meeeeee 8- eee 8-eee Meeeeeeeeee ee Meeeeeeeeee Meeeeeeeee[‌888‌]

Me eee eeee eeeeeeee eeee eeeeeeeee-eeeeeeeee 8-eeeeeeeeeeeee eeeeeee Meeeeeeee eeeeeeeee eeee eeeeeeee, eeee ee eeeeeeeeeeeeee eeeeeeee eeeee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeee eee Meeeeeeee Meeeeeeeeee ee M-(eeee-Meeeeeeeeeeeee)eeeeeeeeeeeee[‌888‌]

Meeeeeeeee eeeeeeeeee eee ee eeeeeeee eeeee eeeeeeeeeeeeee eeeeeee, eeeeeeee ee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeee eeeeeeeee (eee Meeeeee 88.8.8.8.8.8). Meeeeeeee 888, ee eeeeeeeeeeee ee eeeee ee eee eeeeeeeee eeeeeee eeeeeee eeeeeeeeeee, eee eeee eeeeeeee ee eeee eeeeeeeeeee (Meeeee 888).[‌888‌] Meee eeeeeeee ee eeeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeeeeeeee eee eeeeeeeeee ee eeeeeeeeeee eeeeeee ee eee eeeeeeee: eeee eeeeeeeeeeeee ee eeeeeeee, ee eeee eeeee.

Meeeee 888 Meeeeeeeee Meeeeeeee Meeeeeeee eee Meeeeeeee Meeeeeeeeeeeee Meeeeeeeeeee[‌888‌]

Meeeeeeeeeeeeee eee eeee ee eeeeeeee ee eeeeeeeeeeeeee eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeeeeeeeeeee-Meeeeee Meeeeeeeeee ee 8-Meeeeeee-8-ee-8-eee ee Meeeeeeeeeeeeee[‌888‌]

Mee eeeee eeeeeeeeeeee ee eeeeeeeeee 8-eeeeeeeeeeeee ee Meeeeeeee eeeeeeeeee eeeeeeeeeeeeeeeeee eeeeee eee eeeeeeeee eeeeeeeee ee eeeeee eeeeeeeeee.[‌888‌] Mee eeeeee ee ee eeeeeeeeee eeeeeee eee eee eeeeeeeee ee eeeeeeeee-8-eeeeeeeeeee eeeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeee eee Meeeeeeeee Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(8-Meeeeeeeeeeeeeeeeee)eeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M 8-eM eeee, eeeeeeee eeee e eeeeeee eee, eee eeeeeee eeee (M,M)-eeeeeee 888 (88.8ee, 88 μeee). Mee eeeeeeee eee eeeeeeeee ee MM8Me8 (8.8eM) eee eeeeeee eeee MeMM (88 μM, 8.8eeee). Mee eeee eee eeeeeee ee eeee ee ee eeee ee eee eee 88eee, eeee eeeee eeee eee eeeee eeeeeee eeee eeeeee-eee ee eeee eeeee. Mee eeee eee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee ee eeeee eeeee (M,M)-eeeeeeee 888 ee e eeeee eeeee, eeeee eee eeee eeeeeee eeeeeee eeeeeeeeeeee.

Mee eeeeeeee eeeeeee eee eeeeeeeee ee eeeeeee 888 (8.8eeee) eee MMM (88 μM) ee ee. Mee eeeeeeee eeee eee eeeeee ee 8°M eee M8M (88.8 μM, 8.88eeee) eee eeeee eeeeeeee ee eee eeee. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeee eee 8e, ee eeeee eeee eeee-eeeee [(8-eeeeeeeeeee)eeeeeeee]eeeeeeeee (888.8ee, 8.88eeee) eee MMM (888 μM) eeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8e, MMMM (88ee) eee MM8Me8 (8eM) eeee eeeee, eee eee eeeeeee eee eeeeeeee eeeeeee e eee ee eeeeee eee (88e). Mee eeeeee eee eee eeeeee (MeMMe/eeeeeee 8:8, 888eM) eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee MM8Me8 (8eM) eee eeeeee ee 8°M. MMM (8eM) eee eeeee eeeeeeee eee eee eeeeeee eee eeeeeee ee eeee ee ee eeee eeeeeeee. Meeee 8.8e, eee eeee eee eeeeee ee 8°M eee eeeeeee eeee Me8M (88eM) eee eee. ee MeMMM8 (88eM). Mee eeeeeee eeeee eee eeeeee eeee eeeee (88eM), eeeee (Me8MM8), eee eeeeeeeeeeee.

Mee eeeeeee, 888, eee eeeeeee eeee M8 eee eeeeeeeee ee MM8Me8 (8eM) eee eeeeeeee (888 μM, 8.8eeee). Me8M (888ee, 8.8eeee) eee MMMM (88.8ee, 8.8eeee) eeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 88eee, eee eeeeeee eeee Me8M (88eM) eee eee. ee MeMM8 (88eM). Mee eeeeeee eeeee eee eeeeee eeee eee. ee MeMM8 (88eM) eee eeeee (88eM), eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeee ee MMM (8eM) eee eee. ee M8MM8 (8eM) eee eeeeee ee eeeeee eee 8e. Mee eeeeeee eee eeeeeee eeee Me8M (88eM) eee M8M (88eM). Mee eeeeeee eeeee eee eeeeee eeee eeeee (88eM), eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:88).

8-Meeee-8-eeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee Me8MMe8 [eeeeeeee eeee Me8M (88.88e, 88eeee) ee MeMM (888eM) eee Me8 (8.88 e, 88eeee) ee MeMM (88eM)] eee eeeee 8-(eeeeeeeeee)-8-eeeeeeeeeeeee (8.88e, 88eeee) eeeee eee eeeeeee. M eeee ee Me8M (8.88e, 88eeee) ee MeMM (88eM) eee eeeee eeeeeeee ee eee eeeeeee, eee eee eeeeee eee eeee ee eeeee eeeeeeeee. Mee eeeeeee eee eeee eeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee eeeeeee eeeee eeee eeeeeee eee eee eeeeeee eeeeee eeee eeeeeeeeeeee ee ee. 8eM; eee Me8MM eeee eeeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeee eeeeeeeeeeee. Mee eeeeee eeeeeee eee eeeeeeeee; eeeee: 8.88e (88%); ee 8888.8°M/8Meee.

8-Meeeee-8-eeeeee-8-(eeeeeeeeeeeeeee)eeeeeeeee (888):[‌888‌]

M eeee ee eeeeeeeeeeeeeeeeeeeeee (8.8eeee) ee eee MMM (88eM) eee eeeeee ee 88°M eee e eeee ee eeeeeee eeeeeeee M-eeeeeeeeeeeeee (8.88e, 8.8eeee) ee MMM (88eM + 8eM eeeee) eee eeeee ee eeeeeee. Mee eeee eee eeeeeee ee eeee ee 88°M eeee 8.8e eee eeee eeeeeeee ee eeeeeeee ee M8M (8.8eM). Mee eeeeeee eee eeeeeeeee eeee Me8M (88eM). Mee eeeeeee eeeee eee eeeeee eeee M8M (88eM) eee eeeee (88eM), eeeee (MeMM8), eee eeeeeeeeeeee, eeeeeeeee 888, eeeee eee eeee eeeeeeee ee eee eeee eeee.

M eeee ee 888 eee Me8M (8.88e, 8.8eeee) ee MMM (88eM) eee eeeeee ee 8°M eeeee M8 eee MMMM (8.88eM, 8.8eeee) eee eeeee ee eeeeeee. Mee eeee eeeeee eeee eee eeeeeee ee eeee ee ee, eeeeeee eee 88e, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeee 8:88 ee 8:88) ee eeee 888 ee e eeeeeeeee eee; eeeee: 8.88e (88%).

(8M)-8-(Meeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee (M)-()-8-eeeee-8-eeeeeeeeeeee-8-ee (888; 8.8e, 8.8eeee) ee MMM (88eM), eeeee M8, ee 8°M, eee eeeee Me8M(M)Me (8.88eM, 8.8eeee) eee Me8M (8.88eM, 8.8eeee); e eeeee eeeeeeeeeee ee Me8MMMe eee eeeeeeeeeee eeeeee. Mee eeeeeeeeee eee eeeeeee ee 8°M ee ee eee 88e, eeeee eeeee ee eee eeeeeeee ee 8°M eee MeM (8.8e, 88.8eeee) eee eeeee. Mee eeeeeeeeee eee eeeeeee ee 8°M ee ee eee e eeeeeee 88e eee eeee M8M (8 eeeee eeeee ee MeM) eee eeeee. Mee eeee eee eeee eeeeeeee eeeeeee MeMM8 eee eee eeeeeeeee eeeeee eeee eee eeeeee eeee Me8M (888eM). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe) ee eeee e eeeeeeeee eeeee; eeeee: 8.88e (88%); ee 888888°M.

Meeeee (8M)-8-Meeeeeeeeeeeeee-8-eeeeeeeeeee (888, M8=M); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee eeeeeeee eee eeeee eeeeeeeeeee eeee eeeeeee eee ee ee eeeeeeee.

Meeeee (M)-M-eeeeeeeeeeee (8.8e, 8.88eeee) eee eeeeeeeee ee eeeee eeeeeee (8 × 88eM) eee eee eeeeeee eee eeeeeee ee eeeeeeeeeee. Meeeeee (88eM) eee Me8M (8.88eM, 8.88eeee) eeee eeeee eee eee eeeeeee eee eeeeee ee 88°M. MM8Me8 (8.888eM, 8.88eeee) ee eeeeeee (88eM) eee eeeee eeeeeeee eeee 88eee. eee eee eeeeeee eee eeee eee 8e ee 88°M. Mee eeeeeeeeeee eee eeeeeee ee eeee ee ee eee eee eeee eee eeeeeee eeee MeMMe. Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eeee eeeee (88% e/e; 88eM), eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeee ee eee, eeeee eee eeeeeeeeeeee (M8M/eeeeeee/MeMM); eeeee: 888ee (88%); ee 888888°M.

eee-8-(8-Meeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeee (888):[‌888‌]

M eeeeeee ee (8M,8M)-8-eeeeee-M-(8-eeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeee (888; 8.88e, 8.8eeee) ee eeeee MeMM (88eM) eee eeeeee eeeee eeeeeee eeeeeeeee. Me eee eeeeeee eeeeeee eee eeeee eeeeee eee eeeeeeeeeee eeee e 8-eee eeeeee 8.88M MeMMe ee MeMM (88eM, 8.8eeee). Meee eeeeeeeee ee MeMMe eeeeeee eee eeeeeee e eeee eeeeee eee eee eeee eeeeeeeee eee eee eeeee eeeee eee eeeee eee eeeeeeeeeee. Meeee e eeeeee ee 88eee, eee eeeeeeee eee eeeeeee, eee eeeeeee eee eeeeeeeeee, eee eee eeeee eeeeeee eee eeeeee eeee M8M eee eeeeeeee; eeeee: 8.8e (88%); ee 888°M.

References