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40.5.2.1.1.3 Method 3: Synthesis from Cyclic N-Hydroxyimides by Alkylation with Organic Halides

DOI: 10.1055/sos-SD-040-00666

Geffken, D.; Köllner, M. A.Science of Synthesis, (2009401007.

N-Hydroxyimides, easily available from the corresponding anhydrides of dicarboxylic acids and hydroxylamine, are valuable precursors for a plethora of simple and multifunctional alkoxyamines. Alkylation proceeds smoothly with alkyl halides, organic sulfates, methanesulfonates, or 4-toluenesulfonates, by addition to activated double bonds and by Mitsunobu reaction. The resulting N-alkoxyimides can be cleaved either by acidic hydrolysis or by hydrazine hydrate, methylhydrazine, hydroxylamine, aminoethanol, or methylamine to give the desired O-alkylhydroxylamine as the salt or the free base. N-hydroxyphthalimide (317) is used most often, but its hydrogenated derivatives 318320 and the N-hydroxyimides 321326 are also successfully applied in alkoxyamine synthesis (Scheme 120).[‌471‌‌478‌]

Meeeee 888 M-Meeeeeeeeeee Meeeeeee eee eee Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeee ee eee M-eeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeee eeee 888 eeee eeeeee eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeee eeeeee eeeeee ee eeeeeeeeeeee ee eeeeeeeeeee 888 (M8=Me, Me) eee eee eeeeeeeeeee 888 ee e eeeeee eee eeeeeeeeeeee eeeeeeeeee eeeeeee eeee eee e eee eeeeee ee eee eeeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-Meeeee- ee M-Meeeeeeeeeeeeeeeee eeee M-Meeeeeeeeeeeeeeeeeeeeeeeeeee Meeeee Meee[‌888‌]

Me eee eeee eeeee[‌888‌] eeee eee M-eeeeeeeeeeee 888 eee eeeee ee eee eeeeeeee eeeeeeee eee eee eeeeeeeeeee ee eeeeeee eeeeeeeeeeee, eee eeeeee (8888%) eeeee eeeeeeee eeeeee eeee eeeee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee eeee M-eeeeeeeeeeeeeeeeee.

Meeeeeeeeee M-eeeeeeeeeeeeeeeeeee 888, eeeee eee eeeeeeee eeeeee eee eeeee eeee­eeeeeeeeee eeee eeeeeeee eeeeeee eeeeeeeeeee-eeeeeeeee eeeeeee ee Meeeeeeeeeeeee eeeeee, eee eeeeeeeeee ee eeeeeeeeee ee M-eeeeeeeeeeeeeeeeee (888) eeeeeeee ee eeeeeeeeeeeeee (Meeeee 888).[‌888‌,‌888‌‌888‌]

Meeeee 888 Meeeeeeee ee M-(Meeeeeeeeee)eeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 888

M8 Meeeeee Meeee (%) Mee
MM8M 88 [‌888‌]
(MM8)8M 88 [‌888‌]
MM8MM8 88 [‌888‌]

Meeeeee-eeeeeeeeeee M-eeeeeeeeeeeeeeeeeeee 888 eeee eeeee ee eeeeeeeeeeeeee ee eeeeeeeeeeeee ee eeeeeeeeeee eee eee eeeeeeee ee eeeeeeee M-eeeeeeeeeeeeeeeeee (888), eeeeeeeee eeeeeeeee, eee eee eeeeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeee eee M-(eeeeeeeeeee)eeeeeeeeeee, eeeee ee eeeeeee ee eeeeeeeee eeeeeee ee eeeeeee eee eeeeeeeeeeeeee 888 ee eeee eeeeee (Meeeee 888).[‌888‌] Meeeeee eeeeee-eeeeeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeee eee eeeeeeee eeeeeeeeeee ee 8888% eeeeee.[‌888‌]

Meeeee 888 Meeeeeeee ee Meeeeee-Meeeeeeeeee M-Meeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee 888

Me8 Meeeeee Meeee (%) Mee
8-MM8M8 88 [‌888‌]
8-MM8M8 88 [‌888‌]
8-MeM8M8 88 [‌888‌]

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

Meeeee 888 Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeee ee M-Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeee ee M-eeeeeeeeeeeeeeeeee eee 8-eeeeeeeeeeeeee ee eeeeeeeeeeee eeeee ee 888, eeeee eee ee eeeeeee ee eeeeeeeeeeeeeee ee eeee eee M-eeeeeeeee eeeeeeeeeeeee 888,[‌888‌] e eeeeeeeee eeeeeee ee eeeeeeeeeeee[‌888‌] eee eeeeeeeee eeeeeeeee (Meeeee 888).[‌888‌‌888‌]

Meeeee 888 Meeeeeeee ee M-(8-Meeeeeeeeeeee-8-ee)eeeeeeeeeeeee[‌888‌,‌888‌]

M-(Meeeeeeeeeeee)eeeeeeeeeeeee (88%), M-(eeeeeeeeeeee)eeeeeeeeeeeee (88%), eee M-(8-eeeeeeeeeee)eeeeeeeeeeeee (88%), eeee eeeeeeeee M-eeeeeeeee eeeeeeeeeeeeee,[‌888‌,‌888‌] eee eeeeeeee ee e eeeeeee eeeee eeee M-eeeeeeeeeeeeeeeeee eee eeeeeeeeeeee eeeeee eeeee, eeeeeeeeeeee eeeee eeeee, ee eeeee eeeee eeeee, eeeeeeeeeeee, ee eeeeeeeeeeeeeee, eeeeeeee ee eeeeeeeeeeee eeee eeeeeeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeeee.[‌888‌] Mee M-eeeeeeeee eeeeeeeeeeeeee 888 eee eeee eeeeeeee eeee eeeeeeeeee ee M-eeeeeeeeeeeeeeeeee eeee eeeee eeeee eeeee, 8-eeeeeeeeeeee eeeee eeeee, ee eeeeee eeeee eeeee, eeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeeeee;[‌888‌] eeeee eeeeeeeeeeeeee eee eeeeee eeeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeee eeeeee eeeeeeeeee eeeee.[‌888‌‌888‌]

M-(Meeeeeeeeeeeeee-8-ee)eeeeeeeeeeeee (888), ee M-eeeeeeeee eeeeeeeeeeeee,[‌888‌‌888‌] ee eeeeeeee ee 88% eeeee ee eeeeeeee ee M-eeeeeeeeeeeeeeeeee eeee 8,8-eeeeeee-8M-eeeee eee eeeeeeeee eeeeeee ee eeeeeeeeee eeeeeeee ee 8-eeeeeeeeeeeeeee eeee eee M-[(eeeeeeeeeeeeeee-8-ee)eee]eeeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-(Meeeeeeeeeeeeee-8-ee)eeeeeeeeeeeee[‌888‌]

Mee ()- eee (+)-eeeeeeeeeee ee M-(eeeeeeeeeeeeeee-8-ee)eeeeeeeeeeeee (888) eee eeeeeeee eeee 8,8-eeeeeee-8M-eeeee eee eeeeeeeee-M,M-eeeeeeee eeee M-eeeeeeeeeeee. Mee eeeeeee ee eee eeeeeeeeeeeeee eeeeeee ee eeeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeee; eeeeeeeeeeeeee eeeee eee eeeeeeee eeeeeeee.[‌888‌] Meeeeee-eeeee M-(eeeeeeeeeeeeeee-8-ee)eeeeeeeeeeeee 888 ee eeeeeeee eee eeeeeeeeeeee eeee ee eee eeeeeeeeeeeee eeeeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeee-eeeee eeeeeeeee.[‌888‌]

M-eeee-Meeeeeeeeeeeeeeeee eeeeeeeeeeeee (888), e eeeeee M-eeeeeeeee eeeeeeeeeeeee,[‌888‌‌888‌] ee eeeeeeee ee 88% eeeee ee eeeeeeee ee M-eeeeeeeeeeeeeeeeee (888) eeee eeee-eeeee eeeeeee eee eeeeeeeeee eeee eee eeee-eeeeeeeeeeeeeeeee (888), eeeeeeee ee eeeee­eeeeeeeee eee eeeeeeeeeeeee eeee eeeeeeeeeeee eeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-eeee-Meeeeeeeeeeeeeeeee Meeeeeeeeeeee[‌888‌,‌888‌]

M-Meeeeeeeeeeeeeeeeee, eeeee eee eeee eeeee ee ee M-eeeeeeeee eeeeeeeeeeeee,[‌888‌] ee eeeeeeeeeee ee 88% eeeee eeee eeeeee eeeeeeee eee M-eeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeee ee eee eeeeeeeeeeee M-(eeeeeeeee)eeeeeeeeeee.[‌888‌] Meeeeeeee ee eee eeeeeee-eeeee M-eeeeeeeeeeeeeeeeeee 888 ee eeeeeeee ee eeeeeeeeeeee eeeee ee eeeeeeee ee eeeeeeeeeeee-eeeeeeeeeee Meeeeeee eeeeee eee M-eeeeeeeeeeeeeeeeee, eeeeeeee ee eeeeeeeeee eeeeeeeeeeee.[‌888‌]

Meeeeeee ee M-eeeeeeeeeeeeeeeeee, eeeeeeeeeeeee, eee 8-eeeeeeeeeeeeee ee eeeeeeeeeeee ee eeee eeeeeeeeeee, eeeeeeee ee eeeeeeee ee eee eeeeeeeeeeee M-(eeeeeee-8-eeeee)eeeeeeeeeee (888) eeee 88% eeeeeee eeeeeeeeeee, eeeeeeee M-(eeeeeee-8-ee)eeeeeeeeeeeee (888) ee 88% eeeee ee e eeeeeeeeeee eeeeeeee (Meeeee 888).[‌888‌] Meeeeeeeeee, M-(8-eeeeeeeeeeeee-8-ee)eeeeeeeeeeeee ee eeeeeeee ee 88% eeeee.

Meeeee 888 Meeeeeeee ee M-(Meeeeee-8-ee)eeeeeeeeeeeee[‌888‌]

M-(8-Meeeeeeee)eeeeeeeeeeeee (888) ee eeeeeeee eeee M-eeeeeeeeeeeeeeeeee eee 8-eeeeeeeee eeeeeee ee eee eeeeeeee ee eeeeee(M) eeeeeeeeeeeeeeeee eee M-(8-eeeeeeeeeeee)eeeeeeeeeee (888); eeeeeeeeeeeeee ee eee eeeeee ee eeeeeee eeeee eee eeeeeeeeeeeee ee 88% eeeeeee eeeee (Meeeee 888).[‌888‌]

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

Meeeeeeeeeee M-eeeeeeeeeee eeeeeeeeeeeeee 888, eeeee eee ee eeeeeeee ee eeeeeeeeeeeeee ee eeee eeeeeeeee,[‌888‌‌888‌] eee eeeeeeee eee eeeeeeeeeeeeee ee eee eeeeeeeeeee M-(eeeeeeeeeeeeee)eeeeeeeeeeee ee eeeeeee (Meeeee 888).

Meeeee 888 Meeeeeeee ee Meeeeeeeeeee M-Meeeeeeeeee Meeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 888

Me8 Meeee (%) Mee
88 [‌888‌,‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

8-[(Meeeeeee)eeeeee]-8M-eeeeeeeee eeeeeeeeeeeee (888) ee eeeeeeeeeee eeeeeeeee ee 88% eeeee eeee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeeeee ee eeeeeeee eeee eeeeeeeeeeee eeee (Meeeee 888).[‌888‌] M-(Meeee[e]eeeeeeee-8-eeeeeeee)eeeeeeeeeeeee (888), eeeeee ee e eeeeeeee eeeee eee eeeeeeeeee, ee eeeeeeee ee 88% eeeee ee eeeeeeeeeeeeee ee eee eeeeeeeeeee M-eeeeeeeeeeeeeeeee.[‌888‌]

Meeeee 888 M-(Meeeeeeeeeeee)-eeeeeeeeeee Meeeeeeeeeeeee[‌888‌,‌888‌]

M-(8-Meeeeeeeeeeee)eeeeeeeeeeeee eeeeeeeeeeeeeee (888) ee eeeeeeee eeee 8-(eeeeeeeeeeee)eeeeeeee eeeeeeeeeeeee, M-eeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeee ee eeeeeeeeeeee, eeeeeeee ee eeeeeeeeeeeeee eee eeeee eeeeeeeee ee eee eeee eeee eeeeeeeeeeee eeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-(8-Meeeeeeeeeeee)eeeeeeeeeeeee Meeeeeeeeeeeeee[‌888‌]

Mee eeeeeeee ee M-eeeeeeeeeeeeeeeeee eeee α-eeeeeeeeeeeeeee eeeeee ee eeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee eeeeeee 8-(eeeeeeeeeeeeee)eeeeeeee eeeeee 888, eeeee eee eeeeeeeeee ee 88% eeeeeee eeeeeeeeeee eeee ee eeee eee eeeeeeeeeeeee ee 8-(eeeeeeee)eeeeeeee eeeee 888 ee 8888% eeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-(Meeeeeee)eeeeeeee Meeee[‌888‌]

Mee eeeeeeee ee M-eeeeeeeeeeeeeeeeee eeee M-(eeeeeeeeeeeeee)eeeeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee 8-[8-eeeeeee-8-(eeeeeeeeee)eeeeeee]eeeeeeeeeee (888), eeeee ee eeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeeee 8-(eeeeeeee)-8-(eeeeeeeeee)eeeeee-8-ee (888) (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee (8-Meeeeeee)-8-(eeeeeeeeee)eeeeee-8-ee[‌888‌]

Mee eeeeeeee ee 8,8-eeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeee, M-eeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeee, eeeeeeee ee eeeeee eeeeeeeeee, eeeeeee 8,8-eee(eeeeeeee)eeeeee eeeeeeeeeeeeeee (888) ee 8,8-eee(eeeeeeee)eeeeeee eeeeeeeeeeeeeee, eeeeeeeeeeee,[‌888‌] eeeeeeee eeeeee eee eee eeeeeeeee ee eeeeeeee eee eeeeeeeee (Meeeee 888).[‌888‌,‌888‌,‌888‌]

Meeeee 888 Meeeeeeee ee 8,8-Mee(eeeeeeee)eeeeee Meeeeeeeeeeeeee[‌888‌]

8-Meeeee-8,8-eee(eeeeeeee)eeeeee eeeeeeeeeeeeeee (888) ee eeeeeeee ee e eeeeeee eeeeeee ee eeeeeeeeeeeeee ee 8-eeeeee-8,8-eee(eeeeeeeeeeeeee)eeeeee (888) (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-Meeeee-8,8-eee(eeeeeeee)eeeeee Meeeeeeeeeeeeee[‌888‌]

M eeeeeee ee M-[(eee)eeeeeeeeee]eeeeeeeeeeeeee, eeeee eeee eee eeeeeeeee eeeeee ee Meeee 8, eeeee eee eeeeee ee eeeeeeeeee ee eeeeeeeeeeee eeeeeeeeee, eee eeeeeeee ee 8888% eeeeee eeee (eee)eeeeeeeeee eeeeeee eee M-eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee eee eeeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeee M-(eeeeeeeeeeeee)eeeeeeeeeee.[‌888‌]

Meeee 8 M-[(Mee)eeeeeeeeee]eeeeeeeeeeeeee eeee (Mee)eeeeeeeeee Meeeeee[‌888‌]

M-[(Mee)eeeeeeeeee]eeeeeeeeeeeee Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

M eeeee eee eeeeeeeeeeeeeee eeeeeeeeeee ee M-eeeeeeeeeeeeeeeeeee 888 eeeeeee eee eeeeeee eeeeeeee eeeeeeee ee eeeee eeeeeeee eeee M-eeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeeee eeee-eeeeeeee eee Meeeeee 888 (eeeeeeeeeeeeeeeeeeeeee eeeeeeee) ee eeee eee M-eeeeeeeeeeeeeeeeee 888, eeeeeeee ee eeeeeeeeeeee eeee eeeeeeeee eeeeeee ee eeee eeeeeeeeeee (Meeeee 888).[‌888‌] Meee eeeeee eeeeee eeeeeee eeeeeeeeee: (8) eee ee e eeeeeee eeeeeee eeeeeee ee eeeeeee; (8) eeeeeeeeeeeeee eeeeee eeeeeee eeeee eeee eeeeeeeeee; (8) eee eeeeeeeee ee eeeeee eeeeeee eee.[‌888‌] M-Meeeeeeeeeeeeeeeee eeeeeeeeeeeee ee eeee eeeeeeee eeee eeeeeee eee eeeeeeeeee (eee Meeeeee 88.8.8.8.8.8).[‌888‌]

Meeeee 888 Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee eeeeeee e Meeeeee[‌888‌]

Meeeeeeeeee 888

M8 Meeee (%) ee 888 eeee 888 Mee
Me 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
(MM8)88Me 88 [‌888‌]
MM8MMM 88 [‌888‌]
MM8MM8Me 88 [‌888‌]
(M)-MM8MM=MMMM8Me 88 [‌888‌]

M-(8-Meeeeee-8-eeee)eeeeeeeeeeeeee, eeeeeeeeee eeeeee ee eeeeeeeeee eeeeeeeee, eee eeeeeeee ee eeeeeeeeee ee M-eeeeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeeeee-8-eee eee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee, eeeeeeee ee eeeeeeee ee eee M-(8-eeeeeee-8-eeeeeee)eeeeeeeeeee ee 8-eeeeeeeeeeee (Meeee 8).[‌888‌‌888‌]

Meeee 8 M-(8-Meeeeee-8-eeee)eeeeeeeeeeeeee eeee Meeeeeeeee ee M-Meeeeeeeeeeeeeeeee[‌888‌]

M-(8-Meeeeee-8-eeee)eeeeeeeeeeeee Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

M-Meeeeeeeeeeeeeeeeee Meeeeeeeeeeee (888, M8=Me; MMe Meee); Meeeeee Meeeeeeee:[‌888‌]

M 88.8% eeeeeee eeee ee eee eeeeee eeee 888 ee M-eeeeeeeeeeeeeeeeeeeeeeeeeeee (888e, 8.88eee), eeeeeee (888eM), eee Meeeee 8888 (8eM) eeee eeeeeeee ee ee eeeeeeeee. Mee eeeeeee eee eeeeee ee 88°M eee eeeeeeeeee eeeeeeeee eeee MeMe (8.8MMe) eee 8e ee eeee eeeeeeeeeee. Me eeeeeeeeee eee eeeeee eee eeeee eee eee eee eeeeeee eee eeeeeeeeee. M eee-eeeee eeeeee eee eeeeeeee. Mee eeeeeee eeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee M-eeeeeeeeeeeeeeeeeeeeeeeeeeee 888 (M8=Me); eeeee: 88.8e (88%).

Mee eeeeeeeeeee 888 (88e, 8.888eee) eee eeeeeeeee ee M8M (88eM) eee ­MM8MMM8MM8 (8.8e, 8.888eee) eee eeeee, eeeee eeeeeeee, ee 88°M. Meee e eeeeee ee 8e, 88% ee MeMM (88.8e, 8.88eee) eee eeeee. Meeee eeeeeeee eee 8e ee 88°M, eee eeeeeeeeeee eee eeeeeeeee eee eeeeeeeeeeeee 88eM ee eee eeeeeee eee eeeeeee ee eeeeeeeeeeee. Mee eeeeeeeeee eee eeeeeeeee eeee 88% MMe eee eeeeeeeeeeee ee eeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eeeeeeeeeee; eeeee: 8.8e (88%).

M-(Meeeeeeeeeee)eeeeeeeeeeeee Meeeeeeeeeeee (888, M8=MM8M; MMe Meee); Meeeeee Meeeeeeee:[‌888‌]

M-Meeeeeeeeeeeeeeeee (888; 88e, 8.88eee) eee MeMM8M (88.8e, 8.88eee) eeee eeeee ee eee MMMM (888eM) ee 8°M. M8MM8 (888e, 8.88eee) eee eeeee eee eee eeeeeee eee eeeeeee eee 8e. M8 eee eeeeeee eeeeeee eee eeeeeee eee 8e, eeeee eee eeee eeeeee eeee eee eeeee (888eM) eee eeeeeeeee eeee MeMMe (8 × 888eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eee. MeMe eeee eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeee eeee eMe8M eee eeeeeeeee eeeee ee eeee M-(eeeeeeeeeeeee)eeeeeeeeeee; eeeee: 88e (88%); ee 888888°M; MM (eeee) ν̃eee: 8888, 8888, 8888, 8888ee8; 8M MMM (MMMe8, δ): 8.88 (e), 8.888.88 (e).

Me e eeee ee M-(eeeeeeeeeeeee)eeeeeeeeeee (88e, 8.88eee) ee e eeeeeee ee MeMM (888eM) eee M8M (8.8eM) eee eeeee MM8MM8M8M (8.88e, 8.88eee) eee eee eeeeeee eee eeeeeeee eee 8e. Meeee eeeeeee, eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeee eee eee eeeeeeeee MeMM eeee ee eee eeeeeee eee eeeeeee eeee 8M MMe ee MeMM. Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eeeeeeee eeeeeeeee eeeeeeee; eeeee: 8e (88%).

M-(8-Meeeeeeeeeee)eeeeeeeeeeeee (888, Me8=8-MM8M8); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeeeeeeee eeeeeeee (88.8e, 8.888eee) eee M-eeeeeeeeeeeeeeeeee (888; 88.8e, 8.888eee) eeee eeeeeeeee ee MMM (888eM). M eeee ee MMM (88.8e, 8.88eee) ee MeMM (88eM) eee eeeee eeeeeeee eee eee eeeeeeeeeee eee eeeeee ee 88°M. Meeee eeeeeeee eeeeeeee, eeeeeeee eee eeeeeeeee eee eeeeeee 88eee. Mee eeeeeee eee eeeeee eee eeeeee eeee eee eeeee. Mee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee, eeeeee eeee M8M, eee eeeee eeeee eeeeeee eeeeeeee. Mee eeeee M-(8-eeeeeeeeeeeeeee)eeeeeeeeeee eee eeeeeeeeeeeeee (eeeeeee/eeeeeeeee eeeee); eeeee: 88e (88%); ee 888°M.

M-(8-Meeeeeeeeeeeeee)eeeeeeeeeee (88e, 8.888eee), MeMM (888eM), eee MM8MM8M8M (8.8e, 8.888eee) eeee eeeeeeee eee 8e. Meeee eeeeeee, eee eeeeeee eee eeeeeeee eee eee eeeee eee eeeeee eeee MeMM. Mee eeeeeeee eee eeeeeeeee eeee 8M MMe eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeee M8M eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeee eeeeeeee eeee MeMM eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee Me8M, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeee eeeeeee eee eeee eeeeeeeee; eeeeeee eeeee: 88.8e (88%); ee 8888°M/8.88Meee.

M-(Meeeeeeeeeeeeee-8-eeeeeeee)eeeeeeeeeeeee (888, M8=Meeeeeeeeeeeeee-8-ee); Meeeeee Meeeeeeee:[‌888‌]

(Meeeeeeeeeeeeee-8-ee)eeeeeeeeeeeeeeeeee (888, M8=eeeeeeeeeeeeeee-8-ee; 88e, 8.88eee) eee 8-eeeeeeeeeeee (88eM) eeee eeeee eee eeee ee 88°M eee 8e. Mee eeeeeee eee eeeeee eeee M8M eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8e (88%).

M-(8-Meeeeeeeeeeee-8-ee)eeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeeeeeeee ee eeeeee eeeeeeeee eee eee eeee-eeeeee ee eee. Me ee eeeeeeeee ee eeee, eeee, eee eeeeee eeeeeeeee.

M-Meeeeeeeeeeeeeeeee (888; 88.8e, 8.88eee) eee eeeeeeeee ee eee MMM (888eM). 8-Meee­eeeeeeeeee (88eM, 8.888eee) eee eeeee, eeeeeeee ee 8 eeee ee MMMe8. Meeee 88eee, eee eeeee eee eeeeeeeee. Me8M (8eM) eee eeeee eee eee MMM eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeee ee ee MeMMe (888eM), eeeeeeee, eeeeee eeee ee MeMMM8, eeee eeee eee. ee MeMe, eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eee eee eeeee eeeee eee eeeee eeeee eeeeeee eeeeeeee ee eeee 888; eeeee: 88.8e (88%). Me eee eeeeeee ee MMMe8, eeeeeeeee ee 888 eee eeeeeeee ee 8e;[‌888‌] eeeeeeeeeeee MMMe8 ee MeMM eeeeeeeeeee eee eeeeeeeee ee 888.[‌888‌]

Mee eeeeeeeeeee 888 (88.8e, 8.888eee) eee eeeeeeeee ee MM8Me8 (888eM) eee eee eeeeeee eee eeeeee ee ee eee eeee. MeMMMM8 (88.8eM, 8.888eee) eee eeeee eeee 88eee eeeee eeeeeeee. Meeee ee eeeeeeeeee 88eee, eee eeee eeee eee eeeeeee eee eee eeeeeee eee eeeeeee eee 8e. Mee eeeeeee eee eeeeeeee, eeeeeeeeeeee ee e eeeee eeeeee, eeeeeeee eeeee, eee eeeeeeeee eeeee eeeeeee eeeeeeee (8888°M/88Meee) ee eeeeee e eeeeeeeee eeeeee; eeeee: 88.8e (88%). Meeeeeeeeeeeeee eee ee eeeeeeeeeee ee eeeeeeeee.[‌888‌]

M-(Meeeeeeeeeeeeee-8-ee)eeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M-Meeeeeeeeeeeeeeeee (888; 88.8e, 8.8eee) eee MeMMM8M (8e, 8.8eeee) eeee eeeeeeeee ee eeeeeee (88eM). 8,8-Meeeeee-8M-eeeee (88e, 8.88eee) eee eeeee ee eeeeeeee eee eee eeeeeeeeeee eee eeee eeeee 88°M. Meeee eeeeeeee eeeeeeee eee eeeeeeee eee eeeeeee 88eee, eee eeeeeee eee eeeeee eeee M8M eeeeeeeeee MeMMM8 (88eeee). Me eeeeeee, M-[(eeeeeeeeeeeeeee-8-ee)eee]eeeeeeeeeee eee eeeeeee ee eeeeeeeeee; eeeee: 88.8e (eeeee); ee 888888°M; 8M MMM (MMMe8, δ): 8.88 (e), 8.88 (e), 8.88 (e), 8.88 (e), 8.88 (e).

M-[(Meeeeeeeeeeeeee-8-ee)eee]eeeeeeeeeee (8.8e, 88eeee) eee eeeeeeeee ee eeeeeee/MeMM (8:8; 88eM) eee MM8MM8M8M (8.8e, 88eee) eee eeeee. Mee eeeeeee eee eeeeeeee eee 88eee. Meeee eeeeeee, eee eeeeeee eee eeeeeee eeee 8% ee Me8MM8 ee eeeeee eeeeeeeeeee-8,8-eeeee, eee eeee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeeeee eee, eeeee eeeeeeeeee ee eee eeeeeeeeeeee; eeeee: 8.8e (88%); ee 88°M/88Meee (ee 88°M/88Meee[‌888‌]).

M-(8-Meeeeeeee)eeeeeeeeeeeee Meeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeeeeeeeeeee (8.8e, 88.8eeee), M-eeeeeeeeeeeeeeeeee (888; 8.8e, 88.8eeee), MeMM8[‌888‌] (8.8e, 88.8eeee), eee Me8M (888eM) eee eeeeeee eeeee e M8 eeeeeeeeee eee 88e. Mee eeeeeeeeeeee MeMe eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MM8Me8) ee eeee M-(8-eeeeeeeeeeee)eeeeeeeeeee (888). M eeeeeee ee eeeeeeeee eeeeeee ee 888 eee MM8MM8M8M ee MeMM eee eeeeeeee eee 8e, eee eeee eeeeeee eeee 8% Me8MM8 eeee; eee eeeeeeeee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeee eeee Me8M, eee eee eeeeeee eeeee eee eeeee (MeMM8) eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MeMM/MM8Me8 8:88). Meeee eeeeeeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeeeee ee Me8M eee eeeeeee eeee MMe/Me8M. Meeeeeeeeeeeeeeee ee eee eeeeeeeeeeee eeeee eeeeeeee eeeeeeeee eeeeeeee; eeeeeee eeeee: 88%; ee 888888°M.

8,8-Mee(eeeeeeee)eeeeee Meeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: 8,8-Meeeeeeeeeeee ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee eee ee e eeeeeeee eeeee eeeeeeeeee.

Me e eeee ee M-eeeeeeeeeeeeeeeeee (888; 8.88e, 8.88eee) ee eeeee MMM (88eM), MMM (8.88eM, 8.88eee) eee eeeee eeeeeeee, eeee eeeeeeee. Me eeee eeeeeee eee eeeee 8,8-eeeeeeeeeeeee (8.88e, 8.888eee), eee eee eeeeeee eee eeeeee ee 88°M eee 8.8e eee eeee eeeeee eeee eee. Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eeee M8M (88eM) eeeeeeee ee MeMM (88eM), eee eeeeeeeeeeeeee (MeMM) ee eeee 8,8-eee(eeeeeeeeeeeeee)eeeeee. M eeeeeeeeee ee eee eeeeee (8.8e, 8.888eee) ee MMe/eeeeeee MeMM (8:8; 88eM) eee eeeeee ee 888°M eee 8e ee eeee e eeeee eeee. Meeee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee, M8M (88eM) eee eeeee eee eee eeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee 8M MMe. Mee eeeeeeee eeeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeee (MeMM/M8M); eeeee: 8.88e (88%); ee 888°M.

M-Meeeeeeeeeeeeeeeeeeeee [888, M8=(MM8)88Me]; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee M-eeeeeeeeeeeeeeeeee (888; 8.88e, 88eeee), M8MM8 (8.88e, 88eeee), eee Meeeeee 888 (8.88e, 8.8eeee) eee eeeeeeeeee eeeeee eee 88eee ee ee. 8-Meeeeeeeeeeeeee (8.88e, 88eeee) eee eeeee eee eee eeeeeee eee eeeeee ee 88°M eee 8e. Meee, eee eeeeeee eee eeeeee ee ee, M8M (88eM) eee eeeee, eee eee eeeee eee eeeeee eeee M8M eeeee eee eee eeeee eee eeeeeeeeeee; eee eeeeeee eee eeee eeeeeeeeee ee eeeeee ee eeeeee eeeeeeeee eeeee eeeeeee. Meeeeeeeeeeeeeeee (MeMMe) eeeeeeee M-(eeeeeeeeeeee)eeeeeeeeeee; eeeee: 8.88e (88%).

M-(Meeeeeeeeeee)eeeeeeeeeee (8.8e, 88eeee) eee M8MMM8M8M (8eM, 88.8eeee) eeee eeeeeee ee ee eee 88eee. Me8M (88eM) eee eeeee eee eee eeeeeee eee eeeeee eee 88eee. Mee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee Me8M (8 × 88eM). Meeee MMe eee eeeeeee eeee eee eeeeeeee eeeeeee eeeeee, eee eeeee eee eeeeee eeee Me8M, eee eeeeeeeeeeeeee (eMeMM); eeeee: 8.88e (88%); ee 888888°M (ee 888888°M[‌888‌]).

References