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10.13.1.5.2.4 Method 4: Giving C-Carbon Indoles

DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (20102377.

Heterocyclic ring methyl groups can be halogenated via the free-radical mechanism usual for alkylarenes, provided the nitrogen is protected with a methoxycarbonyl, benzoyl, phenylsulfonyl, or tert-butoxycarbonyl substituent (e.g., to give 1305, Scheme 552).[‌804‌,‌866‌,‌1654‌,‌1655‌] Hydroxymethyl substituents at the 4-, 5-, and 6-positions of indoles, can be converted into chloromethyl groups via reaction with thionyl chloride and then a very easy loss of sulfur dioxide at room temperature; in the examples described there is also a 2-ethoxycarbonyl group, which may serve to stabilize the normally very reactive indolylic halide products.[‌1656‌] Without the electron-withdrawing N-substituent it is not possible cleanly to prepare or use (chloroalkyl)indoles in nucleophilic displacement reactions.[‌1657‌] Such indolylic halides behave as normal benzylic halides, being easily displaced by nucleophiles or undergoing dehydrobromination producing the corresponding vinylindole.[‌1658‌] Alkylation of homochiral 2,5-diethoxy-3,6-dihydropiperazines with 3-(bromomethyl)-1H-indoles allows synthesis of enantiomerically pure tryptophans.[‌1659‌]

Meeeee 888 Meeeeeeeeeee ee e Meeeeeeeeeee Meee Meeeee Meeee[‌888‌]

Meeeeeeeeee ee ee eeeeeee eeee ee eeeeeee eeeee ee eeeeeeeee ee 8- eee 8-eeeee eeeeee ee eee eeeeee,[‌8888‌] eee eeeeeeeeeee eeeeeeeeee ee 8-eeeeeeeeeeee eeee 8-eeeeeeeeeee eee ee eeeeeeee eeee eeeeee ee eee eeeeeeeee eeee[‌8888‌] ee eeeeeeeeee eeeee 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee ee eeeeeee eeeeeeeeeeeeeee ee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeee 8888 ee 8888 eee 8,8,8,8-eeeeeeeeeeeeeeeeeee[e]eeeeee ee 8888 ee Meeeee 888.[‌8888‌,‌8888‌]

Meeeee 888 Meeeeeee Meeeeeeee ee Meeeee 8-Meeeeeeee eee 8,8,8,8-Meeeeeeeeeeeeeeeeee[e]eeeeee eeee 8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee[‌8888‌,‌8888‌]

Meeeeeeee ee 8,8-eeeeeeeeeeeeee eeee 8,8,8,8-eeeeeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeeeeeeeeee (8888) eeee eeeee 8-eeeeeeeeeee eeeeeee eeeeeeeee ee eee 8-eeeee eeeeeeeeeee; Meeeee 888 eeeeeeeeeee eeee, eeeee eee eeeeeeeeee ee 8,8,8,8-eeeeeeeeee-8M-eeeeeeeee (88) eeee eeeeee 888.[‌8888‌]

Meeeee 888 Meeeeeee Meeeeeeee ee Meeeee 8-Meeeeeeee eeee 8,8,8,8-Meeeeeeeeee-8-eeeeeeeeeeeeeee Meeeeeeeeeeeeeeee[‌8888‌]

Meeeeeeee eeeeeeeee ee eee 8-eeeee eeeee ee e 8,8-eeeeeeeeeeeee eee eeee ee eeeeeeee; eeeeeeeee eeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee[‌8888‌] ee eeeeeeeeee eeeeeeee eeeeeeeee eee eeeeeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeeeeeee ee 8888 eeee 8888 (Meeeee 888).[‌8888‌] Meeeeeeee ee 8-eeeeeee-8-eeeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee-8-eeeeeeeeeeee eeee eeeeeeeee(MM) eeeee eeeee eee 8,8-eeeeeeeeeeeeee.[‌8888‌]

Meeeee 888 Meeeeeee Meeeeeeee ee Meeeee 8-Meeeeeeee eeee Meeeeeee Meeeeeeee[‌8888‌]

Meeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeeee ee eee 8-eeeee eeeee ee 8,8,8-eeeeeeeeeeeeeee, eee eeeeeee 8,8,8-eeeeeeeee-8M-eeeeee (8888), eeee ee eeeeeee ee eeeeeee ee eeeeeee eeeeeeee 8888 ee eee eeeeee 8888 eeeeeeee ee eeeeeeee ee eeee eeeeeeeeeeeee eeeeeee ee eee 8-eeeeeeee, ee eeeee ee Meeeee 888. Meeeeeeeeeeee eeeeee ee eee eeeeeee β-eeeeee (eeeeee ee 8888) eeeee eeee 8888, eee eeeeeeee eeeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee eeee ee eee eeeeeeeeeeeee eeeeeee eeeeeeeeee eeeee, ee eeee eeeeeeee eeeeeee 8888.

Meeeee 888 Meeeeeeee eee Meeeeeeeeeeee Meeeeeeeeeee ee ee Meeeee 8-Meeee Meeee

Meeeeeee ee eeee eeeeeee e Meeeeee eeeeeeeeeeee [eeeeee M,M,8,8-eeeeeeeeeee-8M-eeeeee-8-eeeeeeeeee (8888) ee Meeeee 888][‌8888‌] eee eeeeeeeeeeeeeeeeeeee[‌8888‌] ee 8,8,8-eeeeeeeeeeeeeee, eeeeeeeee eee eeeee eeeee ee Meeeee 888, eeeeee eeeeeeee eeee eeeeeeeeeeee ee eee 8-eeeeee.

Meeeee 888 Meeeeee Meeeeeee ee ee Meeeee 8-Meeeee[‌8888‌]

Meeeeeeeeeee ee 8-eeeeee-8M-eeeeee ee eee eeee-eeeee eeee eeee eeeeeeeee 8888, eeeeee eeeeeeee 8888, eeeeeeee eeeeeeee eeeeeeeeeee, eee eeeeeeeee eeeee eeeee ee eeee eeeeeeeeeee, ee e eeeeeeeee eeeeeeeee ee eeeee eeeeeeee eeeeeeeeeee eeeee eeeeeeee eeeeee ee eee eeeeee 8-eeeeee; Meeeee 888 eeeeeeeeeee.[‌8888‌]

Meeeee 888 8-(Meeeeeeeee)-8M-eeeeeee eeee 8-Meeeee-8M-eeeeee[‌8888‌]

Meeeeeeeeee 888

M8 Meeee (%) Mee
Me 88 [‌8888‌]
Me 88 [‌8888‌]
(MM8)8Me 88 [‌8888‌]
88 [‌8888‌]

Meee 8- eee 8-(eeeeeeeeee)-8-eeeee-8M-eeeeeee eee ee eeeeeeeee eeee eee eeeeeeeeeeeee 8- eee 8-eeeeeeeeeeeeee eeeee eeeeee eeeeeee ee eeeeeeeeeeeeeeeee ee 88°M; ee ee eeeeeeee eeee eee eeeeeee eeeeee eeeeeeee eee M-eeeee eeeee, eee eeee eee eeeeee ee eeeeee ee eeeeeeeeeee ee 8-eeeeeeeeeeeeeee eeee.[‌8888‌]

Meee-eeeee eeeeeeeeee ee eeeeeeee eee e 8-eeeeeeeeeee, eeeee eeeeeeee eee e 8-eeeeeee eeeeeeeeeee, eeee eeee eeeee M-eeeeeeee/eeeeeeeeee eeeeee,[‌8888‌,‌8888‌,‌8888‌,‌8888‌] eee eeeeeeeeeeee eeee eeeeeee M-eeeeeeeeee/eeeeeeee eeeee e eeeee eeeeee ee e eeeeeeeeeee ee eeeeeeeeeeee eee eeeeeeeee eeee-eeeeeeee.[‌8888‌‌8888‌]

M,M-Meeeeeee-8M-eeeeee-8-eeeeeeeeeee (eeeeeee) eee, eeeeeeeeee, eee eeeeeeeeee eeeee eee eeee eeeeee eeeeeeeee eeeeeeeeeeeee ee eeee eeee eee eeeeee eeeeeeee (eee Meeeeee 88.88.8.8.8.8.8.8.8) eee eee eeeeeeeeeeeee eeeee (ee eeeeeeeeeeeeee ee eee eeee ee e eeeeeee eeeee-eeee) ee eeeeee eeeeeeeee ee eeeeeeeeeeee; eeeeeeeee eeee eeeeeee[‌88‌] eee eee eeeeee ee eeeeeeeeeeeeeeeee,[‌8888‌,‌8888‌] eeeeeeeeeeee,[‌8888‌] eee 8-eeeee eeeeee[‌8888‌‌8888‌] eee eeeeeee. Mee eeee eeeeeeeeeeee ee eee eeeee (eeeeeeee) eeeee eeeeeeee eee ee eeeeee eeeeeeeeeeee, eee ee eee ee ee eeeeeeeeeee, eeeeeeeee eeee ee eee eeeeee M-eeeeeeee ee e eeee-eeeeeeeeeee eeee,[‌8888‌] eee eeee eee eeeeeeeeeeee ee e 8-eeeeeeeeee-8M-eeeeee 8888 eeee 8888, eeeee eeee eeeeeee eeee eee eeeeeeeeeee (eeeeee ee 8888), eeeeeeeeeeee eee eeeeeeee eeeeee 8888 (Meeeee 888).

Meeeee 888 Meeeeee Meeeeeeeeeee ee Meeeeee Meeee-Meee Meeeee 8M-Meeeee-8-eeeeeeeeeeee[‌88‌]

Meee eeeeeeeee eee eeee eeeeeeee ee eeeeeeeee eeee eeee eeeeee eeeeeeeeeeee eeee eee eeeeeeeeeeeee M,M,8-eeeeeeeee-8M-eeeeee-8-eeeeeeeeeee (8-eeeeeeeeeeeee), eee eeeeeeeeeeee ee e eeeeeeeeeeee ee e eeeeeeeeeee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee ee eeeee eee eeeeeeee-eeeeeee eeeeee ee e eeeeee eeeeee.[‌88‌,‌88‌] Me ee eeeeee ee eeeeeeeeeee eeeeeeeeeeeeeeeee ee eeeee eeeeeeeee eee eee eeeeeee eeeeeeeeeeee eeeeeeeeeeee ee eeeeeeee ee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeeee.[‌8888‌,‌8888‌] Meeeeeee eeeeeeeee eee eeee eeeeee.[‌8888‌] M eeeee eeeeee ee eeeeeee eee eeeeeeeeee ee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeeee ee ee eeeeeeeeeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee ee e eeeeeeeeee,[‌8888‌] eeeee eeeeeeee eeeeeeee ee eeeeeeeeeeee eee eeee-eeeee eeeeeeee eee ee eeeeeeeeeeeee eee eeeeee eeeeeeeeeee.[‌8888‌]

Meeeee 888 eeeeeeeeeee eee eeeeeeee eeeee 8-(eeeeeeeee)-M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee (8888) (eeeeee eeee eee eeee) eeee eeeee 8-eeeeeeeeeeeeeee (8888) ee eee eeeeeeeeeee eeeeee 8888.[‌8888‌]

Meeeee 888 8-Meeeeeeeeeeeeee Meeeeeeeeeee ee 8-(Meeeeeeee)-M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee[‌8888‌]

Meeeeeeeeee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeeee (eeeeeeee) eeee e eeeeeee ee eeeeeeee 8888 ee eeeeeeeee eeee eeeeeeee, eeeeeee eee 8-eeeeeeeeee-8M-eeeeee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeee eee eeeeeeee ee e eeeeeeeeeee eeeeee 8888 (Meeeee 888).[‌8888‌,‌8888‌]

Meeeee 888 Meeeeeee ee M,M-Meeeeeee-8-(eeeeeeeeeeeeeeeee)-8M-eeeeee-8-eeeeeeeeeee Meeee-Meee[‌8888‌,‌8888‌]

Mee (eeeeeeeeeeeee)eeeeee eeee ee eeeeeeee eee ee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeee ee eeeeeeee eeee M-eeeeeeeeeeeeeeee, eee eeeeeeeee eeeeeeeee eeeeeeeeeeeee 8-eeeeeeeeeee eeeeeeeee e 8-eeeee-8-[(eeeeeeeeeeeee)eeeeee]-8M-eeeeeeee eeeeee eee eeee eeeee-Meeeeee eeee ee eee (eeeeeeeeeeeee)eeeeee eeeeeeeeeee; eeee eeeeeeeeeeeeee eee ee eeeeeeee eeee eee eeeeeeeeeeee ee e 8-eeeeeeeeeeee eee eeeeeeee eeeeeeeeee (eee Meeeeee 88.88.8.8.8.8.8), eee eeeeeeeeeee ee eee 8-(eeeeeeeeeeeee)eeeeee eeeeeeeeeee eeee eeeeeee eeeeeeeee.[‌8888‌]

Me eeeeeeee eeeeeee eeeeeeeeeee 8888 eeee eeeeeeeeeee eeeee (ee eeeeeeeeeeee eeeee) eeeee eee(eeeeeeeee-8,8-eeeee)eeeeeee eeeeeeeeeeeeeeeee, 8-eeeeeeeeeeeee (ee 8-eeeeeeeeeeee) eee eeeeeeee ee eeeee ee Meeeee 888.[‌8888‌]

Meeeee 888 8-Meeeeeeeeeeee eeee Meeeeee Meeeeeeeeee[‌8888‌]

Meeeeeeeeee 888

M8 M8 Me8 Meeee (%) Mee
M M Me 88 [‌8888‌]
M MMe 8-M8MM8M8 88 [‌8888‌]
MMe M 8-M8MM8M8 88 [‌8888‌]

Meeeeee (8888) eeeeee eeee eeeeeeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeee 8-eeeeeeeeeeeeee 8888 eeeeeeee, ee eeeeeeeeeee ee Meeeee 888.[‌8888‌]

Meeeee 888 8-Meeeeeeeeeeeee eeee Meeeeee[‌8888‌]

Meeeeeeeeee 888

M8 Meeee (%) Mee
8-Mee 88 [‌8888‌]
8-MeM8M8 88 [‌8888‌]
8-MMM8M8 88 [‌8888‌]
8-eeeeeee 88 [‌8888‌]
8-eeeeeee 88 [‌8888‌]

Mee 8-eeeeeeeeee-8M-eeeeee eeeeeeeeeeeee eeeeeeee ee eeeeeee eeeeeeeee eee eeee ee eeeeeeeee ee eeeeeeeeeee eeee, eee eeeeeee eeee eeeeeeeeeeee. Mee eeeeeee, 8-eeeeeeee ee 8-eeeeeee eeeeee eeeeee eee ee eeeeeeee eeee M-eeee-eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee, ee eeeeeeeeeee ee eee eeeeeee (eeeeee ee 8888) ee Meeeee 888.[‌8888‌]

Meeeee 888 8-Meeeeeeeee-8M-eeeeee Meeeeeeeeeeee eeee 8-Meeeeeeeeeeee[‌8888‌]

Mee eeeeeee eeeeee ee eee eee ee eeeee-8-eeeeeeee eeee eeeeeeee 8888: eeeeeeeeeee ee eeeeeeeeeeeee eeeeeeee ee eeeeee eeeeeee ee eee eeeee eee eee eeeeeeeeee ee eee 8-eeeeeeeeee-8M-eeeeee ee eeee eeee; Meeeee 888 eeeeeeeeeee.[‌8888‌] Me eeeeeeee eee eee eeeeeeeeeee eeeee eeeeeeeee eeeeeeee ee eeeeeee, ee eee eeeeeeee ee M-eeeeeee, eee ee eeee eeeeeeeeeee, eeeeeeeeeee eeeeeeeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeee eeee eeeeeeee eeeeeeee.[‌8888‌]

Meeeee 888 8-Meeeeeeeee-8M-eeeeee Meeeeeeeeeeee eeee Meeee-8-eeeeeeee Meee Meeeeeee[‌8888‌]

Mee eeeeeeee[‌888‌] eee eeeeeeeeeeee ee e eeeeeeeeee eeee-eeeee ee e 8-eeeeeeeeeeeee eeeeee, eeeeeeeeee ee eeeeeeeee eeee eeeeee eeeeeeee (Meeeeee 88.88.8.8.8.8.8.8.8), eeeeeeeeee eeee ee eee eeeee, eee eeeeeee 8888 eeee 8888, eeee eeeeeeeee, eee eeee eeeeeee ee eeee eeeeeeeeee, eee eeeeeee ee eee eeeeeeeee ee eee 8-eeeee-8M-eeeeee-8-eeeeeeeeee (8-eeeeeeeeeeeeeee, 8888, Meeeee 888); eeeeeeee ee eee eeeeeeeee ee eee eeeeeeeeee eeee eeeeeee eeeeeeee eeeeeee eee eee eeee-eeeee eeeeeeeee eeee.[‌8888‌]

Meeeee 888 Meeeeeeee ee Meeeeeeeeee Meeee Meeee-8-eeeeeeeeeee Meeeeeee[‌8888‌]

Meee eeeeeeeeee eeeeeeeee ee e eeeeeee eeee ee eee eeeeeee eeeeeeee eeeeeee,[‌8888‌,‌8888‌] eeeeeeee,[‌8888‌,‌8888‌] ee eeeeeeeeeeeeee/eeeeeeeeeeeeeee eeee[‌8888‌] eeeeeeeee ee eeeee-8-ee eeeeeeeee (eeeee eee ee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeee eeeee eeeeee eeeeeeee eeeeee eeee ee eeeeee eeeeeeeeeee[‌8888‌]) ee ee eee 8-eeee eeeeeeeeee eeeeee, eeee eeeeeeeee ee eee 8-eeeeeeeeeee. Mee eeeeeee ee eeee eeeeeeeee eee 8-eeeeeeeeeee eeeeeee.[‌8888‌] Meee e eeeeeeeeeeeeee eeeee ee eeeeeeee, eee eeeeeee eeeeeeee eeeeeee eeee eeeeeeee eeee ee eeeeeeeeeee eee ee eeeeeeeee eeee ee eeeeeeeee eeee ee eee eeeeeeee eeeeeee eeeee; eee eeeeeeeeeee eeeeee eeeeeeeeeee/eeeeeeeeeeeeeee eeee eeeeee eee eeeeeee eee ee eeeeeee ee eeeee ee Meeeee 888 eeeee 8-eeeeee-8-eeeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee (8888) ee eeeeeee ee 8-eeeeee-8-eeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee (8888).[‌888‌] Meeeeeee eeeeeee ee eee eeeeee 8-eeeeeeee ee, ee eee eeee, eeee, ee eee eee eeeeeeeeeeeeee ee eeeee-8-eeeeeeeeee, eeeeee/eeee-eeeeeeeeee/eeeeeeee eeeeeeeeeee ee eeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeee ee e 8-Meeeee-8M-eeeeee ee e 8-Meeee-8M-eeeeee[‌888‌]

8M-Meeeee-8-eeeeee eeeee eeeeeeeeeeeee eeeeee, eeeeee ee eeeeeee ee eeeee ee ee eeeeeeeeeeee.[‌8888‌] Me ee eeeeeee eeee e eeeee eeeeeeeeeeeee ee eee 8-eeeeeeeeee eeeeee ee eee eeeeeeee eeeeeeeeeeee eee eeee eee eeee ee eeeeee eeeeeee eeee eeeeeeeee eee eeeeeeeeeeeeeee ee e β-eee eeee.

Meeeee-8-eeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeee ee M-eeee-eeeee eeeeee-8-eeeeeeeeeeee ee eeeeeeeee eeeeeee, eee eeeee eeeee eeeeeeeeee eeee eee 8-eeeeeeeee eeeeee ee eeeeeeee eeee eeee-eeeee eeeeeeeeee.[‌8888‌] Meeeee-8-eeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeee 8-eeeeeeeee eeee eeeeee eeeee eeee eeeeeeee eeeeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeee.[‌8888‌]

8-(Meeeeeeeee)-8-(eeeeeeeeeeeeee)-8M-eeeeee ee eeeeeeee eeee e 8-eeeeeeeeeeeee eeeeeeeee eeeee eeeeeeeeeeeeeeeeeeeee/eeeeee eeeeee.[‌8888‌,‌8888‌] 8M-Meeeee-8-eeeeeeeee eeeee eeee eee(MM) eeeeeeee eee eeeeeee ee eeee eeeeeeeee[e]eeeeeee, eee eeeeeee 8888; eee eeeeeee ee eeeeeeee ee eeeeeee eeeeeeeeeee eee eeee ee eeeee eeee eee eeeeeee 8M-eeeeee-8-eeeeeeee (8888) ee eeeeeeee ee eeeeeeeee eeeeee, eeeee eeeeeeeee eee eeeeeee ee eeeeee ee ee eeeeee ee eeee 8888, eeeee eeee eeeeee (Meeeee 888).[‌8888‌]

Meeeee 888 Meeee-8-eeeeeeee Meeeeeeee Mee ee Meeeeeee Meeeeeeeee Meeeeee[‌8888‌]

Meeeeeeeeeee ee 8M-eeeeee-8-eeeeeeeeeeeee eeee eeeeeeeeeeee, eeeeeeeee eeee eeeeeeee eeeeeee/eeeeee eeee, eeeeeeeee 8-(8-eeeeeeeeee)-8M-eeeeeee,[‌8888‌,‌8888‌] eeeee eeeeeee eeeeeee eeeeeeeee[‌8888‌] ee eeeeeee eeeeeeeeeee. Meeeeeeee ee 8M-eeeeee-8-eeeeeeeeeeeee, eeeeeeeeee (eeee eeeee) eee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeeee (eeeeeeee), ee eeeeeee eeeee ee eeeeeeeeeee.[‌8888‌]

Mee eeeeeeeeeeee ee eeee 8- eee 8-eeeee eeee-eeeeee eeeee Meeeeeeee’e eeeeeeeeeeeee eeeeeeeeeee ee eeeee ee Meeeeee 888[‌888‌,‌888‌] eee 888.[‌8888‌] Mee 8-eeeeeeeeeee eeeeee 8888 ee eeeeeeee ee eeeeeeeeee ee 8888 eeee eeeeeeeeeeee-8-eeeeeeeeee (8888), eeee eeeeeee eeee eeeeeeeee. Meeeeeee eeeeeeeeee ee 888 eee 8888 eee ee eeeeeeee ee eeeeeeeeee, ee ee eee eeeeeeeee ee 8888 eee 8888, eeeeeeeeeeee. Mee eeeeeeeeeeeee eee eeeeeeeeee eee ee eeeeeeee, ee eeeee eeeeeeeeeeee ee eee (eeeeeeeee) eeeee eeeeee, eee eeeee M-eeeeeeee eeeeeee eee eeeeeeee, eee eeeee eeeeeee eee ee eeeeeeee ee eeee eeee ee eeeee eeeeee ee eeeee M-eeeeeeeeee ee eeee. Me ee eeee eeeeeeee ee eeeeeeeeeee e eeeeee eeeee-8-eeeeeeee eeeee eeeee eeee-eeeeeeeeeeee eeeeeeee eeee eee eeeeeeee ee eeeeee ee eeeeeee eeeeeeeeee eeee eee eeeeeee eeeeeeeeeee (e.e., eeeeeeeee ee 8888 eee eeeeeeeeeee 8888, Meeeee 888).[‌8888‌]

Meeeee 888 Meeeeeeeeeee ee 8-(Meeeeeeeeeee-8-eeeeeeee)-8M-eeeeee[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8-(Meeeeeeeeeee-8-eeeeeeee)-8-eeeeee-8M-eeeeee[‌8888‌]

Meeeee 888 Meeeeeeeee ee ee Meeee-8-eeeeeeee Meeeeeeeeee[‌8888‌]

Meeeeeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeee ee e 8-eeeeeeeeeeee (ee ee 8888) eeee ee e eeeeeee eeeee eeee ee eeeeee ee ee eee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee (eeeeeee) eeeeeeeee eeeeeeeee eeeee, eee ee eeee ee eeeee, ee eee ee eeee eeeeeeeeeee ee eee eeeeeee ee M-eeeeeeee; eeeeeeeee ee 8888 eee 8888 eeeeeeeeee eeee (Meeeee 888).[‌8888‌]

Meeeee 888 Meeeeeeeeeee Meeeeeeeeeeee ee Meeeeeeeeeeee eeee e 8-(Meeeeeeeeeee-8-eeeeeeee)-8-eeeeee-8M-eeeeee[‌8888‌]

Meee 8- eee 8-eeeee-8M-eeeeeee eeeeeeeeee eee eeeee eee, eeeeee eeee eee eeeeeee ee eeeeeeeeeeeeee eee eee eee eeeeee eeeeeee, Meeee–Meeee eeeeeee eee ee eeeeeeee eeee eeee ee eeeee eeeeeeeeeeeee ee eee eeeeee eeee ee eee eeeeeee eeeeee eeeeeeee ee eeeeeeee eeeeee ee eeeeeee.[‌8888‌,‌8888‌] 8-Meeeeeeeeeee eeeee eeeee- eee eeeeeeeeeeeeeeeee eeee eeeeeeeee,[‌8888‌] eee eeee eeeee eeee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee ee eee eeee-eeeee, e.e. 8888, eee ee eeee ee eeeee eeee eeeeeeee-eeee eeeeeeeeeee eeeee eeee (ee eeeeeeeeeeeeeee eeee) eeeeeeeee eeeeee eeeeeeee eeee ee 8888 (Meeeee 888).[‌8888‌] Mee eeeeeeee ee e 8-eeeeeeeeeeeeee eeeeeeeeeee eeeee eee eeeeeeee ee 8- ee 8-eeeeeeeeeeee eeeeee.[‌8888‌,‌8888‌] Meeeeeeee, eeeeeeeeeeeeee Meeee–Meeee eeeeeeeeeeee ee 8-eeeeeeeeeeee ee eeeee eee eeeeeeeeee ee eeeeee ee eeeeeeee eee e eeeeeeee eeeee, eeee ee, eee eeeeeeeeee eee 8-eeeeeeeeeee, eeeee eeeeeeee eee eeeeeeeeeee eeee eeeeee.[‌8888‌]

Meeeee 888 Meeee–Meeee Meeeeeee ee e 8-Meeeeeeeeeeee[‌8888‌]

M eeeeee ee eeeeeee eee eeee ee eeeeeeee 8,8-eeeeeeeeeee-8,8-eeeeeee-8M-eeeeeee (eeeeee-8,8-eeeeeeeeeeeeeee), eee eeeeeee 8888 eeee 8888, eeeeeee ee eeeeeeeeeee eeeeeeeeeeeee eeeee eee ee eeeeee ee eeeeeeeeeeeeee,[‌8888‌‌8888‌] ee eeeeeeeeeee ee eee eeeeeeeee ee 8888 ee Meeeee 888.[‌8888‌]

Meeeee 888 Meeeeeeeeeeeee Meeee–Meeee Meeeeeee ee ee Meeeee-8,8-eeeeeeeeeeeeee[‌8888‌]

8-Meeeeee-8M-eeeeee-8,8-eeeeeeeeeeeeee eeeeee eeee eeee eeeeeeeeeeeee eeeeeeeeeee; eeeeeee eeeeeeee eee eeeeeeee-eeeeeeeeeee eeeee eeeeeee eeeeee 8-eeeeeeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeeee, eee eeeeeee eeeeeee 8888 (Meeeee 888).[‌8888‌] Meeeeeeeee ee 8-eeeeeee-8,8-eeeeeeeeeee-8,8-eeeeeee-8M-eeeeee (8888) eeee 8-eeeeeee-8,8-eee(eeeeeeeeeee)-8M-eeeeee (8888) eeeee eeeee ee eeeeeeee ee eeeeee; ee eee eeee eeeeeee eeee eeeeeee eeeeeeeeeee[‌8888‌] eee eeee [88]eeeeeeeee.[‌8888‌] Me eeeeeeeeeee eeeee ee eeeeee-8,8-eeeeeeeeeeeeeee ee eeeeeee eeeeeeeeeee ee eeeee eeee eeeeeee eeeeeeeeeee ee eeeee eee 8-eeeeeeeeeee eee ee eeeeeeeee eeeeeeee, eeee ee ee eeeee.[‌8888‌] Meeeee-8,8-eeeeeeeeeeeeeee eee ee eeeeeeee eeee 8-[(eeeeeeeeeeeeee)eeeeee]-8M-eeeee-8-eeeeeeee eeeeeeeeeeeeeeeee eeeee ee eeeeeeee ee eeeeee eeeeeeee ee eeee eeeeeeeeeee.[‌8888‌]

Meeeee 888 Meeeeeeeeeeeee Meeee–Meeee Meeeeeee ee e 8,8-Meeeeeeeeee-8,8-eeeeeee-8M-eeeeee[‌8888‌]

8-(eeee-Meeeeeeeeeeeee)-8,8-eeeeeeeeeee-8,8-eeeeeee-8M-eeeeee (8888) ee eeee eeeeeeeee ee eeeeeeee eeeeee ee 8888, eeee ee e eeeeeeeeeee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee (eeeeeee) eeee e 8-eeeeeeeeeeeeeeeeeeee eeeee, eee eeeeeee eeee eeeeeeeeeee eeeeee, eee eeeeeee, 8888 (Meeeee 888).[‌8888‌]

Meeeee 888 Meeeeeeeeeeeee Meeee–Meeee Meeeeeee ee e 8,8-Meeeeeeeeee-8,8-eeeeeee-8M-eeeeee[‌8888‌]

Meeeeeeee ee 8888 eeee eeeeee eeeeeeee eeeeeeee eeeeeeeeeee ee eeeeeee eeee eee 8-(eeeeeeeeeeeeeeeeeeee) eeeee eeee eeeeeeeee ee e eeeeee eeeee eeee ee eeeeeeeeeeeeee. Me ee eeeeeeeee eeee eee eeeeeee eeeeeee eee e eeee ee eeeee eee eeeeee eee eeeeeeeee eeee eee eeeeee, eeeeeeeeee e 8,8-eeeeee 8888 eeeee eeeeeeeee eeeeeeeeeeeeee eeeeee 8888, eee eeeeeee, eeee eeee ee eeeeee ee e eeee eeeee (Meeeee 888).[‌8888‌]

Meeeee 888 Meeeeeeeeeeeee ee 8-[(Meeeeeeeeeeeee)eeeeee]-8M-eeeeeee ee eee Meeeeeee ee Meeeee Meeeeeee[‌8888‌]

8,8-, 8,8-, eee 8,8-Meeeee eeeeee eee ee eeeeeeee (eee eeeeeee) eeee eee eeeeeeeeeeeee eeeeeeeee eeee eeeeeee eeee eeeeeeeeeeee ee eee eeeeeeeeeee, ee eeeeeeeeeee ee Meeeee 888.[‌8888‌,‌8888‌] Meeeeeee ee 8,8-eeeeeeee-8-eeeeee-8-eeeeee-8M-eeeeee ee eee eeee eeeeeeeeee eeeee ee eee 8,8-eeeee, eeeeeeeee eee 8-eeeeeeee. Meeeee-8,8-eeeeee eee eeee eeeeee ee eee eeeee ee eeeeee ee eeeeeeeeeeee eeeeeeeeee. Meee, eeeeeeee ee eeeeeeee eeeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeee eeeeee eeeee ee eeeeeeee ee 8- eee 8-eeeeeeeeeee eeeeeeee. Me eeeeeeeeeee eeeeeeee eeee 8,8-eeeeeeeeeeeeee eeeeeeee eeeeeee eeee e eeeee eeeeeeeeeeeee ee eee 8,8-eeeeeeee (Meeeee 888).[‌8888‌]

Meeeee 888 Meeeeeeeee eee Meeeeeee ee ee Meeeee-8,8-eeeee[‌8888‌]

Meeeee 888 Meeeeeeee ee Meeeee Meeeeeeeeeeeee[‌8888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee 8-(Meeeeeeeeee)-8M-eeeeee-8-eeeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeee MMM (8.88 e, 88 eeee) eee MMMM (88 ee) eeee eeeee ee e eeee ee eeeeee 8-eeeeee-8M-eeeeee-8-eeeeeeeeeee (8.88 e, 88 eeee) ee MMe8 (888 eM) (MMMMMMM: eeeee) eee eee eeeeeee eee eeeeeee eee eeeeee ee 88–88°M eee 8 e. Meeeeeeeeeee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeeeee ee eee eeee eeeee, ee eeeeeeeeeee eeee eeeeee, eee eeeeeeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.

8,8-Meeeeeeeeeeeeeee[e]eeeee-8(8M)-eee (8888); Meeeeee Meeeeeeee:[‌8888‌]

Me ee eee-eeee eeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeee[e]eeeeee (888 ee, 8 eeee) ee e eeeeeee ee MMM (8.8 eM) eee M8M (8.8 eM), eeeeeeeeeeee ee eeeeeee ee M8 eeeeeee eee eeee eee 88 eee, MMM (888 ee, 8.8 eeee) ee MMM (8 eM) eee eeeee eeeeeeee eeee 88 eee eeeee eeeeeeeeeee eee M8 eeeeeeeeee. Meeee eeeeeeee eee 8 e, eeeeee eeeee eeee eee eeeeeeeeeee eeee ee eeee ee eee eeee, eee eeeeeee eee eeeeeeeeeeee. Meeeeeeeee ee eee eeeeeee eeee MeMMe (8 × 88 eM) eee eeeeeeeeeeeee ee eee eeeeeee, eeeeeeee ee eeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe), eeee eee eeeeeee; eeeee: 88 ee (88%); ee 888–888°M.

8,8-Meeeeee-8M-eeeeeeee-8(8M)-eee (888); Meeeeee Meeeeeeee:[‌8888‌]

8,8,8,8-Meeeeeeeee-8M-eeeeeeeee (88; 8.8 e, 8.88 eeee) eeeeeeeee ee MeMM/M8M (8:8) eee eeeee eeeeeeee ee e eeee ee 8,8,8,8-eeeeeeeeeee-8-eeeeeeeeeeeeeee eeeeeeeeeeeeeeeee (8888; 8.88 e, 8.88 eeee) ee eee eeee eeeeeee eeeeeee (88 eM). Meeee eeeeeeee eee 8 e, eee eeeeeee eee eeeeeeeeeeee ee 8–88 eM; eeee eeeeeee (8.8 e) eeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeee eeee M8M (8 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee ee eeeeeee eeeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee, MeMMe). Meeeeeee eeee eee eeeeeeeeeee eeeeeeeee eee eeeeeeee eeee eee eeeeeee eeeeeeeeeee eee eee eeeee eee eeeeeeeeeeeeee (MeMM) ee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.

8,8,8,8,88,88,88,88,88,88-Meeeeeeee-8M-eeeeeeeeee[e]eeeee-8-eee (8888, e = 8); Meeeeee Meeeeeeee:[‌8888‌]

M8M8 (888 ee, 8.8 eeee) eee eeeee ee e eeeeeee eeee ee 8,8,8,8,88,88,88,88,88,88-eeeeeeeee-8M-eeeeeeeeee[e]eeeeee (8888, e = 8; 888 ee, 8.8 eeee) ee M8M/MMM (8:8; 88 eM) ee ee. Meeee 8 e, eee MMM eee eeeeeeeeee ee ee eee eee eeeeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eee eeeeee eeee M8M, 8% ee Me8M8M8, eee. ee MeMMM8, eee eeeeeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee. Meeeeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee), eeeeee eee eeeeeee; eeeee: 888 ee (88%); ee 888–888°M.

M,M,8,8-Meeeeeeeeee-8M-eeeeee-8-eeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌8888‌]

88% Me Me8MM (88.8 eM, 88 eeee), 88% ee MMMM (8.8 eM, 88 eeee), eee 8,8,8-eeeeeeeee-8M-eeeeee (8888; 8.8 e, 88 eeee) ee MeMM (88 eM) eeee eeeeee eeeeeeee ee 88°M eee 8 e. M8M (88 eM) eee eeeee ee eee eeeeee eeeeeee, eee eeee MeMM eee eeeee ee eeeeee eee eeeeeee eeeeeeee eeeeeeee eeeee eeeee Me8M eee eeee ee eeeeeee eeeeeee eeeeeeee. Meeee eeeeee eee eeeeeeeeeeeee, e eeeee eee (8.88 e) eee eeeeeeee, eeeee eee eeeeeeeee ee 888–888°M/8.888 Meee ee eeee eee eeeeeee ee ee eee; eeeee: 8.88 e (88%); ee (eeeeeeeeee) 888–888°M.

8M-Meeeee-8-eeeeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M eeeeeee ee M,M,M-eeeeeeeee-8M-eeeeee-8-eeeeeeeeeeeeee eeeeee eeeeeee (88 e, 8.8 eee) eee MeMM (88.8 e, 8.8 eee) eeeeeeeee ee M8M (888 eM) eee eeeeee eee 8 e ee 88–88°M. M eeeeeeeee eee eeeeeeeee. Mee eeeeee eeeeeee eee eeeeeeeee eeee Me8MM8, eeee Me8M eee eeee ee eeeeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeeeeee eeeeee eeeee eeeeeeee ee e eeeeee eee; eeeee: 88.8 e (888%); eeee eee eeeeeeeee ee 888°M eee 8.8 Meee ee eeee eee eeeeeee; ee (eeeeeee) 888–888°M.

Meeee 8-[8-(Meeeeeeee)-8M-eeeee-8-ee]-8-eeeeee-8-eeeeeeeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌8888‌]

8-(Meeeeeeee)-M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee (8.88 e, 88.8 eeee), eeeee 8-eeeeeeeeeeeeeee (8.88 e, 88.8 eeee), eee eeeeeee (88 eM) eeee eeeeee ee eeeeee eeeee M8 eee 8.8 e. Me eee eeeeee eeeeeee, MMMe8 (888 eM) eee eeeee. Mee eeeeeee eee eeeeee ee eee eee eeeeee eeeeeeeeeeee eeee 88% ee MMe (8 × 88 eM), M8M (88 eM), 8% ee MMM (8 × 88 eM), M8M (88 eM), eee eeeee, eee eeee eeeee (Me8MM8) eee eeeeeeeeeeee ee eeee eee eeeeeee ee ee eee; eeeee: 88.8 e (88%).

8-(8-Meeeeeeeee)-8M-eeeeee (8888, Me = MM8MM8); Meeeeee Meeeeeeee:[‌8888‌]

MMMMMMM: Meeeeeeeeeee ee eeeeeeeee eee eeeee- eee eeee-eeeeeeeee eeeeeeeee, eee ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee.

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeeeeeeeee ee eeeeeeeeeee eeeeeee eee eeee eee ee eeeee.

M,M-Meeeeeee-8-(eeeeeeeeeeeeeeeee)-8M-eeeeee-8-eeeeeeeeeee eee eeeeeeeeeee eeee MeM (8.8 eeeee) ee eeeeeee (MMMMMMM: eeeeeeeeee) ee ee eee 8 e ee eeeeee, eeeee eeeeeeeeeeeee, eee eeeeeeeeee ee e eeeee eeeeee ee eeeeeeeeeee eeeeeeeeeeee eeeee. 8 M MMMM ee MMM (8.8 eeeee) eee eeeeeeee eeee e eeeeeeeeee ee eee eeeeeeeeee eee MeMM8 ee MMM eee eee eeeeeeeee eeeee eeee eee eeeeeee ee ee eee 8 e. Meeee eeeee eeeeee eee eeeeeeeeeeeeeee eeeeeeeeeeee, eee eeeeeee eee eeeeeeee; eeeee: 88%; ee 88–88°M.

8-Meeeee-8-eeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

Me MMM (88 eM) eee eeeee MeMM8 (8 eeeeeee, 88 eeee) ee 8°M eeee 88 eee. Meee, 8-eeeeee-8-eeeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee (8888; 8.8 e, 8.8 eeee) eeeeeeeee ee MM8Me8 (88 eM) eee eeeee eee eee eeeeeee eee eeeeeee ee ee eeeeeeeee. Meeeeeee eeee M8M (88 eM) eee eeeeeeeeeeee ee eee eeeeeeee ee MeMM ee 8°M, eeeeeeeeee ee eee eeeeee, eeee ee-eeeeeeeeee ee eee eeeeeee eeeee eeee MM8Me8 eeee, eeeeeeeee eeeeee eeeeeeeeee eee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MM8Me8 8:8), eee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.

8-Meeeee-8-eeeeee-8M-eeeeee (8888); Meeeeee Meeeeeeee:[‌8888‌]

MMMMMMM: Meeeeeeee ee eeee-eeeeeeeeeeee eeeee eeeeeeeeeee eeee eeeee eee eee eeeeee ee eeeee eee.

8,8-Meeeeeee-8M-eeeeee (8.88 e, 88.8 eeee) ee MMM (88 eM) eee eeeeee ee -88°M eee 8.8 M MeMe ee eeeeee (8.8 eM) eee eeeee eeeeee eeee 8 eee. MM8 eee eeeeeee eeeeeee eee eeeeeee ee -88°M eee 88 eee eeee eeeeeee eee eeeeeeeeee eee ee 8°M. Mee eeeee eee eeeeee eeee eeeee eee MMM (88 eM) eee eeeee. Mee eeeeeee eee eeeeee ee eeeeee M8 eee 8.8 M e-MeMe ee eeeeeee (8.8 eM) eee eeeee eeeeee, eeeeeeeee e eeeeee eeeeee eeee. Mee eeeeeee eee eeeeee ee -88°M eee 88 eee, eeeeeeee ee -88°M, eee eeee 8-eeeeeeeeee (8.88 e, 88.8 eeee) eee eeeee. Meeee 8 e ee -88°M, 8 M ee M8MM8 (88 eM) eee eeeee eeeeee ee -88°M. Mee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM) eee eee eeeeeeee eeee eeeeee eeee M8M eeee eeeee (MeMM8) ee eeee, eeeee eeeeeeeeeeeee, 8-eeeeeee-8-eeeeee-8-eeeeee-8M-eeeeee. Meeeeee eeee ee 888°M eee 8 eee ee eeeee eeeeeeeeeeeeeee, eeee eeeeeeeeeeeeee ee eee eeeeeee (eeeeee eee, eeeeee) eeee eee eeeeeee ee ee eee; eeeee: 8.88 e (88%).

References


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