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Please login to access the full content or check if you have access via Zinc Insertion into the C—X Bond and Cross Coupling

DOI: 10.1055/sos-SD-207-00504

Undheim, K.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20131721.

The zincations of hetaryl halides are performed using some form of activated zinc. In the Rieke preparation of active zinc 7, zinc(II) chloride in tetrahydrofuran soln is reduced by preformed lithium naphthalenide. The finely divided zinc is then allowed to react with a hetaryl halide. Metal insertion leads to a nucleophilic hetarylzinc halide. For C—C bond formation, transition-metal catalysis is generally used (Scheme 3).[‌16‌] In an alternative and less potent activation of the metal, zinc dust or finely cut zinc foil is employed. The metal is first treated with 1,2-dibromoethane and subsequently with chlorotrimethylsilane to give the activated zinc 8 (Scheme 3).[‌17‌]

Meeeee eeeeeeeee ee eeee eeee eeeeeee eeeeeee eee eeeeeeee eeeeeeee e eeeeeeeeee eeeeee eee eee eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeee eeeeeeeee.[‌88‌] Mee eeeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeee eeeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeeeee eee e eeeeee eee eeee-eeeeeeee eeeeeeeeeee ee e eeeee eeeee ee eeeeeeeeeeeeee eeee- eee eeeeeeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee eeeeee e eeeeeeeee eeeeeeeeeee eeeee (88–88 °M) eee eee ee eeeeeeee ee eeeee-eeeee eeeeeeeeeeee. Meeeeeeeeeeeeee ee e eeeeee eee eeeeeeeeee eeeeeee. Meeee eeeeee, eeeee eeeeeeee eee eeeeeeeeeeeeeeeee, eeeeeeeeeeeeeeeeeeee eeeeeeee, eeeeeeeeeeeeeeeee, eeeeeeee eeeeeeeee, eeeeeeeeeeee, eee eeeeeeeeeeeeeee. Meee eeeeeeeeeee ee eeeeeee eeee eeeeeeeeee eeee eeeeee [8 eeeee; 888 eeee, eeeeeeeee ee eee eeeeeeee ee 8,8-eeeeeeeeeeeee (8 eee%) eee eeeeeeeeeeeeeeeeeeeee (8 eee%)], eeee 8% eeeeeeeeee ee eeeeeee eeeee 88 eeeee ee 88 °M. Me eee eeeeeeee ee 8.8 eeeeeeeeeee ee eeeeeee eeeeeeee, eeeeeee, eeee eeeeeeeeee eeee eee eeeeeeeeee eeee ee eeeeeeee eeeee 8 eeeee.

Meeeee 8 Meeeeeeeee ee Meee Meeee eee Meeeeee Meeee Meeeeeee: Meeeeee Meeeeeeeee[‌88‌,‌88‌]

Mee eeeeeeee ee ee eeeeeeee-eeeeeeeeeee eeeee ee eee eeeee ee eeee eeeeeeee eeeeeeeee eee eeee ee eeeee eeeeeeeee. Meeee eeeee eeeeeeeeee, eee eeeeeeeeeeeee eeeeeeeeeee eeeeeee eee ee eeeeeeee ee eeee eeeeeeeeeee (>88% eeeeeeeeee). Mee eeeeeeeee ee eeee ee eee eeeeeee ee eeeeeee eeeeeeee eee eeee ee eeeeeeeeeeee ee 88 °M eeee e eee eeeee. Mee eeeeeeeeee eeeeeee eeee eeeeeeee eeeee eeeeeee eeee eeeeee eeeeeeeeeeeee. M eeeee eeeee ee eeeeeeeeee eeeeeeee eeeeeee eeeeeee ee eeeee, e eeeeeee, ee ee eeeee eeeee eee eeeeee ee eeeeeeee ee eeee eeeeee eee eeeeeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeeee. Mee eeee eeeeeeeeee eee ee eeeeeee ee eeeeeeeee. Meeeee eeeeeee eee eeeeeeeee eee eeeeeeeeee eeee eee eeee eeeeeeeee eeeeeeeee. Meee, eeee- eee eeeeeeeeeee eeeeeee eeeeeee e eeeeee eeeee eee eeeeeeee ee eeee eeeeee ee e eeeeee eeee eeeeeeeee eeeeeeee ee eeee eeeeeeeeeee.

M eeeeee eeeeeeeee eee eeeeeee eeeeeee ee eeeeeeee. Meeeeee eeeeeeeeeeeee, ee eeeee eee 8-eeeeeeeeeeee ee Meeeee 8, eeeee eeeeeee eeee eeee eeeeee ee eeeeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeee ee eeee eeeeeeeeeee eeee eeeeee eeeeee 88%. Mee eeeeeeeee eeeeeeeeee eeeeeeeee eee ee eeeeeeeeeee eeeeeee eeee e eeee eeeeeee ee eeeeeeeeeeeee eeeee eeeeeeeeee-eeeee eeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeeeeee. M eeeeeeee eeeeeee eeeee 8-eeeeeeeeeeee eee eee 8-eeeeeeee eeeeeeee ee eeeeeeeee ee Meeeee 8. Mee eeeee-eeeeeee eeeeeee 8 ee eeeeeeee ee 88% eeeee.

Meeeeeeee ee eeee eeee e M—Me eeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeee 8-eeeeeeeeee-8-eeeeeeeeeee eeee eeee/eeeeeee eeeeeeee, eeeee eeeeeeeee eee eeeeeeeeeeeee 8-eeeeeeeee eeeeeee 88 ee 88% eeeee eeeee 88 eeeee ee 88 °M. M eeeeeeeeee eeeeeeee eeee 8-eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) (8 eee%) eeeeeee eee 8-eeeeeeee eeeeeee ee 88% eeeee (Meeeee 8).

Meeeee 8 Meeee Meeeeeee ee Meeeeeeeeee Meeeeee eeeee M—M Meeeeeeee eee Meeeeeeeeeeeee: Meeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeee eeeeeeeee ee eee Meeeeee eeeeeeee eee eeeeeeeeee eeee e eeeeeee ee eeeeeeeeee eeeeee.[‌88‌] Meee, eee eeeeee eeeeeeeee ee eeeeee, eeeeee, eeeeeeee, eee eeeeeee ee eee eeeeeee eee eee ee eeeeeeeeee eeeeee. Meee eee eeeeeeee eeeeee eeeeeeeee(MM) eeeeeee (8 eee%) eee 8-(eeeeeeeeeeeeeeeeeeeee)-8′,8′-eeeeeeeeeeeeeeeee (MMeee; 8 eee%), eeeeeeeee eeeee eeeeeeeee eeeeeee eeeeeee eeee eeeeeeee eeeeeee eeeee eeeeee (8.8 eeeee) eee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeee (8.8 eeeee) eee ee eeeeeee eee ee 88 °M ee eeeeeee eee eeeeeee eee eeeeeeeee eeeeee 88 eee 88 (Meeeee 8). Meee eeeeeeeee eeeeeee ee eeee eeeeee.

Meeeee 8 Meeee Meeeeeee ee Meeeeeeeeee Meeeeee eeeee M—M Meeeeeeee eee Meeeeeeeeeeeee eeee Meeeeee eee Meeeeeeee Meeeee[‌88‌]

Meee eeeeeeee eeeeeee eeee eeeeeeee-eeee eeeeeeeee (eeee ee 8-eeeeeeeeeee eeeeee), eee eeeeeeee-eeee eeeeeeeeeeee (eeee ee 8-eeeeeeeeeee eeeeeeee), ee eee eeeeeeeeee eeeeeee eeeeeee 88, eeeee eeeeeeee. Meeee eeeeeeee ee eee eeee eeeeeee eee eeeeeeee ee 88 °M, eee eeeee eeeeeeee ee eeeeeee eee eeeeeeeee eeeeee eeeeeeee eee eeeee-eeeeeee eeeeeeee ee 88–88% eeeee.

Meeeeee ee eeeeeeeee eeeeeeee eeeeee eeee eeeeeee eeeeee eeeee eeeeeee. Meeeeee eeee, eeeee- ee eeeeeeeeeeee eeeee eeeeee eeee eee 8-eeeeeeeeeee eeeeeee (88) eeeee eeee eeeeeeee eeeeeeeeee eeeee 8 eee% ee eeeeeeeee(MM) eeeeeee eee 8-(eeeeeeeeeeeeeeeeeeeee)-8′,8′-eeeeeeeeeeeeeeeee ee eeee 8 eee% ee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee eeee e eeeeee ee 88 eeeee. Mee eeeeeee eeeeeee eeeeeeee eeeeeeee 88 eee eeeeeeee ee eeee eeeeee (Meeeee 8).[‌8‌]

Meeeeeee eeeeeeeee eeee 8-eeeeeeeeeee eeeeeee eee eeeeeee ee eeeeeeee eeee eeeeeee ee eeeeeeee ee eeee eeeeee. Mee eeeeee eeeee ee 8- ee 8-eeeeeeeeeee eee eeeeee eeeeeeeee ee eee eeeeeeee, eeeee eeeeeeee ee eeeeeee eee eeeee-eeeeeee eeeeeeee 88 ee eeee eeeeee. Me eee 8-eeeeeeee, eeeeeee, eeeee ee e eeeeee eeeeeeeee ee eee eeeeeee ee eee eeeeeeee eeeeeeee, eeeee eeee eeeeeeee e 88% eeeee ee eee eeeee-eeeeeee eeeeeee 88 (M8 = MM; M8 = M8 = M) (Meeeee 8).

Meeeee 8 Meeee Meeeeeee ee Meeeeeeeeee Meeeeee eeee Meeeeeee eee Meeeeee eeeee M—M Meeeeeeee eee Meeeeeeeeeeeee[‌8‌]

Meeeeeeeeee 8

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

Meeeeeeeeee 8M

M8 M8 M8 Meeee (%) Mee
MM M M 88 [‌8‌]
M MM M 88 [‌8‌]
M M MM 88 [‌8‌]

Meeeeeee eeeeeeeeeee eeeeeeee eeee eeeeeee eeeeeee eeee eeeeeeee eeee. Mee eeeeeeee ee 8-eeeeee-8-eeeeeeeeeee eeeeeee eeee 8-eeeee-8-eeeee-8-eeeeeeeeeeeee ee eee eeeeeeeeeeee, eeeee eeeee ee eee eeeeeeeee eeee eeee eeeeeeeee ee eee eeeeeeeeeeeee 8-eeeeeeeeeeee eeeeeeeeee 88 ee e eeeeeeee eeeee eeeee eee eeeeee eeeeeeee eeeeeeeeee (Meeeee 8).[‌8‌] Meee 8-eeeee-8-eeeeeeeeeeeeeee, eeeeeeeeeeeeee eeeeeeee eeeeee ee eee eeeeeeeeee eeee ee eeeeee eee eeeeeee 88. Meeeeeee eee eeeeeeeeee eeeeeeee eee eeee ee eeeeeeee, ee eeee ee eee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeee eeeee eeeeeeeeeeeeeeee eeeeeeee eee 8-eeeeeeeeeeee eeeeeeeeee 88 (M = Me).

Meeeee 8 Meeee Meeeeeee ee Meeeeeeeeee Meeeeee eeee Meeeeeeeee eeeee M—M Meeeeeeee eee Meeeeeeeeeeeee[‌8‌]

Meeeeeeeeee 8

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

M eeeeee eeeeeeeee eeeeeeee ee 8- eee 8-eeeeeeeeeee eeeeeeee 88 ee eeeeeeeee eeeee Meeee eeee eee eee eeeeeeeeeeeee eeeeeeeeeeeeee (Meeeee 8).[‌88‌] Mee 8-eeeeeeeeeee eeeeeeee eee eeeeeee eeeeeeeee eeee 8-eeeeeeeeeeeeee, eeeeeee 8-eeeeeee eeeeeeee eeeeeee eeee eeee eeee eeeeeee eeeeeeeee. Meeee eeeeeeee, eee eeeee eeeeee eee eee eeeeeeeeeee ee 8-eeeeeeeeeee eeeeeee eeeeeeee eeeeeee eeeeeeeeee ee e 8-eeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeeeee eeee eeeee ee eeeeeee eee eeeeeeeeeeeee 8-eeeeeee eeeeeeee eeeeee. Meee eeeee, eeeeeee, eee eeeeeeeee eeeeeeeeeee eeee ee eee eeeeeeeeeee eee eeeeeeeee eeeeeeeeee, eee eeeeeeeeee ee eeeeeee eeee eeeeeeeee, eee eeeeeee eeeeeeeeee eeeee eeeeeeeee. Me eeeeee eeeeeeeeee eeeee eeeeeeeee Meeee eeee, eeeeeee, eeeeeeeeeee eeeeeeee eee eeeeeee ee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeee eeee eeeeeeeeee. M eeeee ee eeeee-eeeeeeee eeeeeeeee eeeeeee 8-eeeeeeeeeee eeeeeee eee eeeee 8-eeeeeeeeee-8-eeeeeeeeeee ee eeeee 8-eeeeeeeeeeeeee-8-eeeeeeeeeee eeeeeee eeee eee eeeeee eeee eeeeee eee eeeeeeee eeee eeeeeee eee eeeeeeee eeeeeee ee eee eeeeeeeeee eeeeeeee. Meeeeeeee ee e eeeee-8-eeeeeeeeeeee eeeee eeeee ee eee eeeeeeee eeeeeeeee eeeeeeeee eee 8-eeeeeeee. Mee 8-eeeeee eeeee eee eeeeeeee 88 (Meeeee 8).

Meeeee 8 Meeee Meeeeeee ee Meeeeeeeeee Meeeeee eeeee M—M Meeeeeeee eee Meeeeeeeeeeeee eeee 8-Meeeeeeeee-8-eeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8

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

Meeeeeee ee 88–88 eee% ee eeeeeee eeeeeeee ee eee eeeeeeee eeeeeee (eee eeeee eeeeeeeee) eeeeeeee eee eeeeeeee eeeeeeee.[‌88‌] Meee 8-eeeeeeeeeeeeee eee 8-eeeeeeeeeeeeeeeee, eeee eeeeeee eeee eeeeee eeee eee 88 eee% ee eeeeeee eeeeeeee, eee eeeeeeee ee Meeee eeee. Mee eeeeeeeee ee eeeeeeee eeeee 8 eeeee ee eeeeee. Mee eeeeeeeeee eeeee-eeeeeeee eeeeeeeee eeee eeee eee eeeeeee eeeeeee eeeee eeeeeeeee eeeeeeeee eeeeee eee eeeeeeeeeeeee eeeee-eeeeeee eeeeeeee ee eeeeeeee ee eeee eeeeee.

Meeeeeeeeeeeee, eee eeeeeeee eeeeeeeee eee eeeeeeeeeeee ee eee eeeeeeee ee 8-eeeeeeeeeee eeeeeee ee e eeeeeee ee eee eeeeee eee eee eeeeeeeee(8) eeeeeeee ee eeeeeeeeeeeeeee.[‌88‌] Mee eeeeeeeeee eeeeeeee ee eeeee ee eee eeeeeeee eeeeeee ee eee eeeeeee eee e eeeeeee ee eeee eeeeeeeeeee. Meee eee eeeeeeee ee eee eeee eeeeeeeeee eeeeee ee e eeeeee eeeeeee eee eeeee-eeeee eeeeeeeee.

Meeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeeeeeee eeeeeee eee ee eeeeeeee ee eee eeeeeeeeee eeeeeeeee eeeeeeeee eee eeeee eeeeeee eeee 8-eeeeeeeeeee ee eeeeee eee eeeeeeeeeeeee eeeeeeee ee 88 eee 88% eeeee, eeeeeeeeeeee. Mee eeeeeeee eeeeeeee eeeeeee 8-eeeeeeeeeeeeeeeee eeeeeee eee 8-eeeeeeeeee, eeee eee ee eeee eeeeeeeeeee eee 8 eeeee, eeeeeeee eee eeeeeee eeeeeee ee eeeeeeeee eeeee.[‌88‌]

Meeee-8-eeeeeeeeeeee eee eeeeeeeeeee eee eeeeeeeeee eeeeeeee ee eeeeeeeeeeeee ee eeeeeee eeeeeeeee.[‌88‌] Meeeee ee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeee ee eeeeeeeee ee eee eeeee eeeeeeee ee 8-eeeeeeeeee-8-eeeeeeeeeeee (Meeeee 8). M eeeeeeeeee eeeeeeeee ee eeeeeeeeeeee ee eeeeeeeee(8)-eeeeeeeee eeeee eeeeeeee eeee eeeeeeeeeee eeeeeeee. Mee eee eeeeeeeee eee eee eeeee eeee eeeeeeeeee eee eeee eeee eeeeee. Mee eeeeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeee ee eeeeee eeee eeee eee eeeeeeeeeeeee eeeeeee.[‌88‌,‌88‌]

Meeee eeeeeeee, ee eee eeeeeee eeee eee eeeeeeeeeee ee 8-eeeeeeeee 8-eeeeeeeeeeeeee eeee 8,8-eeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeeee eeeeeee eee eeeeeee eeeeeeeee ee eeeeeee eeeeeeeee ee eee 8-eeeeeeee.[‌88‌]M eeeeee eeeeeeeee eeeee eee eee eeeeee eeeeeeeeeee ee 8-eeeee-8-eeeeeeeeeee eeeeee, eeeeeee, eee eeeeee eeeeeeeee eeee 8-eeeee-8-eeeeeeeeeeee (88) eee eeeeeeeee eeee ee eeeeeeeeeeeeee eeeeeeeee ee eee 8-eeeeeeee eeeee eeee eeeeeeeeee (Meeeee 8). Mee 8-eeeeeeee eeeeeeee 88 ee eeeeeee eeeee eeeeeee eeee eeee eeeeeee, 8-eeeeeeeeeee 8-eeeeeeeeeee, ee 8-eeeeeeeeeeeeeee. Meeeee 8 eeeee eeeeeeeee ee eee 8-eeeee eeeeeeeeee 88.

Meeeee 8 Meeee Meeeeeee ee e Meeeeeeeeee Meeeeee eeeee Meeeee Meee Meeeeeeee eeee e M—M Meee[‌88‌]

Meeeeeeeee ee eeeeeeeeeee eee eeeeeee eeee eeeee eee ee eeeeeeeee ee eeee eeeeeeeeeeeeeee ee eeeeeeeee(8)-eeeeeeee eeeeeeee eeeeeeeee.[‌88‌] Meee 8-eeeeeeeeee 88 eee 8-eeeeeeeeee 88 eeeeeeeeeee, ee eeeee eee eeeee eeeeeeee ee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeee, eee eeeeeee eeeeeeeee ee eeee eeeeee ee eeeeee eeeeeeee eeeeeee eeee eeee eeeeeeeeeee 88 eee 88,eeeee eeeeeee eeeeeeeee eeeeeeeee-eeeeeeeee eeeee-eeeeeeee eeeeeeeee eeee eeee eeeeeee ee eeee eeeeee ee eeeeeeee eee eeeeeeee 88 eee 88, eeeeeeeeeeee (Meeeee 88). Meeeeeeeeeee eeeeeeeee eeee eeeeee, eeeeeeeee eeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeee eee 8,8-eeeeeeeeeeeee, eee ee eeee eee eee eeeeeeeee eeeeeeee, eeeee ee eeeeeee eee ee eeeeeeeeeeeeeeeee ee 88 °M eee eee 8-eeeeeeeeee eeeeeeeeeee eee ee eeeeeeeeeeeeeee ee 88 °M eee eee 8-eeeeeeeeee eeeeeeeeeee. Meeeeeeee ee eee eeeeeeee eeeeeee eeeee eeeee eeeeeeeeee eeeeeeee 8–8 eeeee eee eeeeeeeeee. Mee eeeeeeeee-eeeeeeeee eeeee-eeeeeeee eeeeeeee ee eee eeeeeeee 8-eeeeeeeeee 88 eeee 8-eeee-8-(eeeeeeeeeeeeeee)eeeeeee (8.88 eeeee eeeee ee eee eeee eeeeeeeee) eeeee eee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee(8) (8 eee%) eee eee-8-eeeeeeeeeeeeee (8 eee%) eeeeeeeee eee eeeeeeee eeeeeeeeee 88 ee 88% eeeee. Mee eeeeeeee eeeeeeee ee eeeeeeee eeeeee 88 eeeeeee ee eeee eeeeeeeeeee. Mee eeeeeeee 8-eeeeeeeeee eeeeeeeeee 88 ee eeeeeeeee ee Meeeeee eeeeeeee eeee eeeee eee eee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee(8)/eee-8-eeeeeeeeeeeeee eeeeeeee eeeeee; eee eeeeeeee ee eeeeeeee eeeee 8 eeeee eeeee eeeeee ee eeeeeeeeeeeeeee. M eeeeee ee eeeeeee eeeeeeeee eee ee eeee eeee eee eeeeee eeeeeee eeee eeee eeeeeeeeeee.

Meeeee 88 Meeee Meeeeeee eeee Meeeeeeeeee[‌88‌]

Mee eeeeeeeee eeeeeee [8,8-eee(8,8-eeeeeeee-8-eeeeeeee)eeeeeeee-8-eeeeeee]eeeeeeee(8-eeeeeeeeeeeeee)eeeeeeeee(MM) (88, MMMMMM-MMeee) ee eeee ee e eee eeeeeeeeeee Meeeeee eeeee-eeeeeeee eeeeeeee eee eee eeeeeeeeeee ee eeeeee eeeeeeeeeeeeee, eeeee-eeeee-eeeeeeeeeee eeeeeee.[‌88‌] Me e eeeee ee eee eeeeeeee eeeeeee eeeeeee eeeeeee eee eeeeeeee eeeeeeee eeeeeeee, e eeeeeee ee eeeeeee eeeeeeeee eee eeeeeeee eeee eeee eeeeeee ee eeeeeeeee eeeeee. Meeeeee eeeeeeeeee ee eeee ee eeeeeee eeeeeee eeeeeee eeeeeeeeee eeeeee eee/ee eeeeeeeeee eeeeeeeee eeeeeeeeeeee eee eeeeeeeeee ee eeeeeeeee eeeeee eeeee eeee eeeeeeeeee. Mee eeeeeeeee ee eee eeeeee eeeee-eeeeeee eeeeeeee, 88 eee 88, ee eeeeeeeeeee ee Meeeee 88.

Meeeee 88 Meeee Meeeeeee ee Meeeeeeeeee Meeeeee eeee eee MMMMMM-MMeee Meeeeeee eeeee Meeeeeeee Meee Meeeeeeee eeee M—M Meeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee Meee (8) eee Meee Meeeeeeee; Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeeeee eeee eeeeeeeee eeeee eeeee. M eeeeeee ee eeeeeeeeeee (8.88 e, 88 eeee) eee Me (88 ee, 88 eeee) ee eeeee MMM (8 eM) eee eeeeeee ee ee eee 88 e. M 8.8 M eeee ee MeMe8 ee MMM (8.8 eM, 8.8 eeee) eee eeeee eeeeeeee eeee 88 eee. M eeeee eeeeee eee eeeeee, eeeee eee eeeeeeeeeee (8888 eee, 88 eee). Mee eeeeeeeeeee eee eeeeeeeee, eee eee eeeeeeeee eeeeeeeee eeee eee eeeeeeeee ee eeeee MMM (8 eM).

Mee eee eeeeeeeee eeeeeeee, eee eeeeeee eeeeee (8.8 eeee) eee eeeee eeeeee, eee eee eeeeeee eee eeeeeee ee ee eee 8–8 e. Mee eeeeeee eee eeeeeeeeeee (8888 eee, 88 eee) eeeeee eee eeeeeeeeeee eee eeeeeeeeeee eee e eeeeeee eeee eeeeeee eeeee eeeee eeeee eee eeeeeeeee ee eeeeeee eeeeeeeee.

Meeeeeeee Me (8) eee Meee Meeeeeeee; Meeeeee Meeeeeeee:[‌88‌]

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

M eee eeeee-eeeeee 88-eM eeeee eeeeeeee eeee ee eeeee eeeee, e eeeeeeee eeeeeee eee, eee e eeeeeeeeeee eee eeeeeee eeee Me eeee (888 eeee, Meeeeee, 8.88 e, 88 eeee). Mee eeeee eee eeeeeee eeee eeeee, eee 8,8-eeeeeeeeeeeee (ee. 888 ee, 8.88 eeee) ee MMM (8.8 eM) eee eeeee. Mee Me eeeeeeeeee eee eeeeee eeeeeee eeee e eeee eee eeeee eeeeeeeee ee eeeeee eeeeeeee (88 e ee 8 eee). Meeeeee eee eeeeeeee eeeee, eee eee Me eeeeeeeeee eee eeeeeee ee eeeee 88 °M (8 eee). MMMMe (ee. 8.88 eM) eee eeeee eeee eee eee eeeeeee eee eeeeeee ee eeee eee 8 eee.

M 8.8 M eeee ee e eeeeeee eeeeee (8 eeee) ee MMM eee eeeee ee 88 °M. Mee eeeeeee eee eeeeee ee 88 °M eee 8 e, eeeeee ee ee, eee eeeeeee eeee MMM (8 eM). Meeeeeee eee eeeeeee eee eee eeeeeeeee Me eeee eee eeeeeee ee eeeeee (ee. 8 e). Mee eeeeeeeeeee eeeeee eeeeeeeee eee eeeeeeeeeee eeeeeee, eeeee eeeee ee eeeeeeeeeee ee e eeeeeee eee eee ee eee eeee eeeeeeee eeee. Mee eeeeeeeeeeeee ee eee eeeeeeeeeee eeeeee eee eeeeeeeeee ee MM eeeeeeee ee ee eeeeeee. Mee eeeeeeee eeeeee eee eeeee eeee e eeeee eeeeee ee eeeeeeee ee eeeeee ee eee eeeeeeee eeeeeeee. Mee eeeeeee eeeee Me eeeeeee eee eeeeeeeeeee ee eee eeeeeee eeeeee eee eee eeeeeeee eeeeeeee eee eeeeeeeeee. Meeee eee eee ee eee Me eeeeeeeee, eee eeeeeeee ee eeeee eeeeeee (eeee eeee 8%) ee eee eeeeee eee eeeeeeeeee ee eeeeeeeeee e eeeeeeeeee ee e eeeeeeee eeeeeee. M eeeeee eeeeeee eee eeeee eee eeeeeeeee ee eeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee eeeeeee eeeeee eee eeeeeeee eeeeeeee eee eeeeeeeeee. Mee eeeee eeeeeee Me eee Me(Me/Me) eeee eee eeeeeeee eeeee eeee eeeeeeeee ee 8–8%.

Meeee 8-(8-Meeeeee)eeeeeeee (8); Meeeeee Meeeeeeee:[‌88‌]

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

Meeee MeMe (8 eeee) eee eeeeee ee ee eeeee-eeeeeee eeeee eee eeeee eee 88 eee ee 888–888 °M eeeee eeee eeeeee (8 eeee). Me eeeeee [8 eeee, 8.8 eeeee, 888 eeee (Meeeeeeee) ee 888 eeee (Meeee)] eee eeeee eeeee eeeee eee eee eeeeeeeeeeeee eeeeeee ee Me eee MeMe eee eeeee eeeee eee 88–88 eee ee 888–888 °M eeeee eeee eeeeee (8 eeee). Mee eeeee eee eeeeeeeee eee eeeeeeee eeee eeeee (8 ×). MMM (8 eM) eee eeeee eee eee Me eee eeeeeeeee eeee 8,8-eeeeeeeeeeeee (8 eee%) eee MMMMe (8 eee%). 8-Meeeeeeeeeee eee eeeeeeeeeeee eeeee eeee ee ee. Mee eeeeeeeee eeeeeeee eee eeeeeeee eeeee 8 e ee ee. Mee eeeee eee eeeeeeeee ee ee 88% eeeee eeeeeeeee eeee M8.

Meeee 8-eeeeeeeeeeee eee Me(MMe8)8 (8 eee%) eeee eeeee ee eee eeee eeeeeee eee eee eeeeeee eee eeeeeee ee 88 °M. Mee eeeeeeee eee eeeeeeeeee eee eeeeeeee eeeee 8 eee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeee ee MM eeeeeeee ee eeeeeeee eeeeeeee eeeee eeeeeeeee eeee eee. ee MM8Me. Mee eeeeeeee eee eeeeeeee eeee eee. ee MM8Me (8 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM) eee eee eeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee; eeeee: 88%.

8-Meeeeeeeeee Meeeeee (88); Meeeeee Meeeeeeee:[‌8‌]

M 888-eM eeeee-eeeeeeee eeeee eee eeeeeee eeee Meeee eeeeee Me (8; 8.88 e, 888 eeee) ee MMM (888 eM). 8-Meeeeeeeeeeee (88.8 e, 888 eeee) eee eeeee ee eee eeeee eee e eeeeeee eeeee eeeeeeee ee ee. Meeee eee eeeeeeee eee eeeeeeeee, eee eeeeeeeee eeeeeee eee eeeeeee ee eeeeee. Mee eeeeeeeee eeeeeeee eee eeeeeeeee ee MM eeeeeeee ee eee eeeeeee. Mee eeeeeee eee eeee eeeeeeeee ee eee eee eeeee eeeeeeee eeeeee eee. Mee eeeeeeeeeee eee eeeeeeeeeee eeee e 888-eM eeeeee eee eeee eeeeeee eeee eeeee MMM ee 888 eM.

8-(8-Meeeeeeeeeeee)eeeeeeee (88, M8 = M8 = M; M8 = MM); Meeeeee Meeeeeeee:[‌8‌]

Me(MMe8)8 (8.88 e, 8 eee%) eee 8-eeeeeeeeee (8.88 e, 8 eeee) eeee eeeeee ee e 88-eM eeeee-eeeeeeee eeeee eee e 8.8 M eeee ee 8-eeeeeeeeeee eeeeeee ee MMM (88 eM, 88 eeee) eee eeeee eee eeeeeee. Mee eeeeeeeee eeeeeee eee eeeeee eeeee eeeeee eee 88 e eeeee eeeee eeeeeee. Mee eeeeeee eee eeeeeee ee eeeee ee eeeeee eee. ee MM8Me eee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eee. ee Me8M8M8 eee eeeee, eee eeeee (MeMM8). Meeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) eeee eee eeeeeee ee e eeeee eeeee; eeeee: 8.88 e (88%); ee 888–888 °M.

8-Meeee-8-eeeeeeeeeee Meeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Me eeee-eeeee 888-eM eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeee eee eee eeeee eeeee eee eeeeee eeeee ee eeeee eeeeeeeeee. 8.8 M Meeee Me (8) ee MMM (88 eM, 88 eeee) eee eeeee ee eee eeeee eee eeeeeee. Mee eeeee eee eeeeee ee ee eee eeee eeeeee e eeee ee 8-eeeee-8-eeeeeeeeeeee (88; 8.8 e, 88 eeee) ee MMM (88 eM) eee eeeeeeeeee eeee eee eeeee eeeee eeeee eeeeeee. Meeee eee eeeeeeee eee eeeeeeee, eee eeeee eee eeeeeee ee eeee eeeeeeeee, eee eeee eee eeeeeee eee eeeeeee ee ee eee 8 e. Mee eeeee eeeeeeee eee eeeeeee ee eeeeee ee eeeeeee eee eeeeeeee eeeee ee eeeee eeeeeeeee. Mee eeeeeeeeeee eee eeee eee eee eeeeeeeeee eeeeeeee eeeeeeeee.

8-[8-(Meeeeeeeeeeeeee)eeeeee]-8-eeeeee-8,8,8-M-eeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

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

M 8-eM, eeeee-eeeeee eeeee eeeee eeeee eee eeeeeee eeee Me eeee (888 ee, 8 eeee; Meeeeee, 888 eeee) eee eeeee MMM (8 eM). Meeee eeeeeeeeee eeee 8,8-eeeeeeeeeeeee eee MMMMe, eee eeeeee 88 (888 ee, 8 eeee) ee MMM (8 eM) eee eeeee. Mee eeeeeee eee eeeeee ee 88 °M eee 8 e. MMM eeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeee ee eee Me eeeeeee 88. Mee eeeeee Me eeee eee eeeeeee ee eeeeee eee eee eeeee eeeeeeeeeee eeee ee eee eeeeeeeeeee eeeeeee eee eeeee ee 8 °M ee e eeee ee 8-eeee-8-(eeeeeeeeeeeeeee)eeeeeee (888 ee, 8.88 eeee), Me(eee)8 (8 ee, ee. 88 µeee), eee (8-eeeee)8M (88 ee, 88 µeee) ee MMM (8 eM). Mee eeeeeee eee eeeeeee eee 88 eee ee ee eee eee eeeeeeee eee eeeeeeee eeee ee MM8Me. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM), eee eeeeeeee eeee eeeeee eeee M8M eee eeeee, eee eeeee (MeMM8). Mee eeeee eeeeeee eeeeeeee eeeee eeeeeee ee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (Me8M) eeeeeeeee eee eeee eeeeeee eeeeeeeeee ee e eeeee eeee; eeeee: 888 ee (88%).