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31.5.1.5.2.1 Variation 1: Diels–Alder Reactions

DOI: 10.1055/sos-SD-031-00299

Thomas, A. W.Science of Synthesis, (200731344.

(Trimethylsilyl)(vinyl)ketene (32) is a remarkably stable liquid that is easily prepared. It is inert to standard [2+2] cycloaddition reactions with alkenes and 1,3-dienes (Section 31.5.1.5.1.1), presumably because of the hyperconjugative effect of the silicon atom. Nevertheless, this reagent does participate as a diene in [4+2] cycloaddition reactions with dienophiles, including alkynes or naphtho-1,4-quinone, to give the respective trimethylsilylated phenols (Scheme 12). These compounds can be easily protodesilylated to the silicon-free phenols in good yields.[‌16‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeeeee Meeeeee eeee eee Meeeeeeeeeeee Meeeeeeee ee (Meeeeeeeeeeeee)(eeeee)eeeeee eee Meeeeeeeeeee[‌88‌]

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

Meeeee 88 Meeeeeeee ee M-Meeeeeeee Meeeeee eeee 8,8-Meeeeeee-8,8-eeeeeee-8M-eeeee-8-eeee eee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeeee MeM88 Meeee (%) ee 88 Mee
M Me M M MMMMM 8888 [‌88‌]
Me Me M M MMM 88 [‌88‌]
MM8Me Me M M MMM 88 [‌88‌]
M MM8Me MM8Me M MMM 88 [‌88‌]
MM8Me MM8Me MM8Me M MMM 88 [‌88‌]

Meee-eeeeeee eeeeeeeeeeeeee [8+8] eeeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeee 88 eeeeeeeeeee ee M8 ee 8-eeeeee-8-eeee ee 8-(eeeeeeeeeeeeeee)eee-8-eeee eeee eeeeee eeeeee eee eeeeeeeeeeeee 8,8-eeeeeee-8M-eeeee-8-eee 88 (e=8) ee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eee 88 (e=8), eeeeeeeeeeee (Meeeee 88).[‌88‌,‌88‌] Meeeeeeee, eeeeeeeeeeee eeeeeeeee [8M-8-eeeeeeeeee-8,8(8M)-eeeee, 88] eeeeee eeee eeeeeeeeeeeeee eeeeeeeeeeeeee eeee eeeeee eeeee eeeeeeeeee ee eeeeeee eeeeeeeeeeeeeeeeeeeeee ee eeeeee eee eeeeeeeeeee eeeeeeeee 88 (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeeeeeee Meeeeeeee eeeeeee Meeeeeeeeeee Meeeeeeeee eee Meeeeee[‌88‌‌88‌]

Me eeee eee eeee eee eeeeee 8-eeeeeeee-8-eeeeeeeeeeee eee eeeeeeeee eeeeeeeeee eee eee eeeeeeeeeeee ee eeeeeeee eeeeeee eeeeeee eeeeeee-eeeeeeee-eeeeee [8+8] eeeeeeeeeeeee eeeeeeeee eeee eeeeeeee-eeeeeeeee eeeeeee; eee eeeeeee, e eeeeeeeeeeeee eeeeeee eeeeee 8-eee-8,8,8,8-eeeeeeeeee-8M-8-eeeeeeeeee-8-eeeeeeeeeee (88) eee 8,8-eeeeee-8-eee eeeee eee eeeeeeeeeeeeeeeeeeee-8-ee 88 ee 88% eeeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee ee e Meeeeeeeeeeeeeeeeeee-8-ee eeee Meeeee 8-Mee-8,8,8,8-eeeeeeeeee-8M-8-eeeeeeeeee-8-eeeeeeeeeee eee 8,8-Meeeee-8-eee[‌88‌,‌88‌]

Meeeeeeeeeeeee eee eeeeeee-8,8-eeeeeee eeeee eee eeeeeeeee eeeeeeeeee ee eeee eeeeeee eeeeeeee eee eeeeeee eeeeeee eeeee eee eeeee eeeeeeeeeee eeeeeee MeeeeMeeee eeeeeeee eeeeeeeeee. Mee eeeeeee, eee eeeeeeeee eeeeeeee 88 eee ee eeeeeeeee eeee eee eeeeeeee 88 eee eee eeeeeeee-8-eeeee 88 ee eeeee eeeee. Mee eeeee ee eeeee eeeee ee eeeeeeeeee e 8,8-eeeeeeee ee eeeeee ee eeeeee, eeeee ee eeeeeeee eeeeeee e eeee-eeeeeeee Meeeeee-eeee eeeeeeeeeeee. Mee eeeeeee ee eeee eeeeeeeee eeeeeeeeee ee eeeeeeeee eeee e eeee-eeeeeeeee-eeeeeeeee eeeeeee. Mee eeeeeee eeeee ee 88%. Meeeeeeeeeeee, eee eeeeeeee 88 eee ee eeeeeeeee eeee eee eeeeeeeeeeee eeeeeeeee 88, eee eeee ee eeee eeeeeee eeee eee 8-eeeeeeeeeeee eeeeeeee-8-eeeee 88 ee eee eeeeeeee ee eeeeee eeeeeee ee eeee eee eeeeeee eeeeeeeeee 88 (Meeeee 88).[‌88‌‌88‌] Mee eeeeeeeee 88 eee 88 eee eeee ee eeeeeeee eeeeeeeeeeeee ee eeeee ee eee eeeeee eeeeeeeee eeeeeeeeee eeeeeeeeeeeeee M. Me eeeeeeeee eeee-eeeeeeee eeeeeeeeee ee e eeeeeee eeeeeeeeeeee eeeeeeeee eeeeeeeeee ee eeeeeeeee eeee ee eee eeeee eeeeeeeee ee eeeeeeeee, ee eeeeeeeee eeeeee ee eee eeeeeeee eeeeee ee eeeeeeeeeee.[‌88‌]

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

M eee-eee eeeeee eee eee eeeeeeeeeeeeee eeeeeeeee ee eeeeeee-8,8-eeeeeeee 88 ee eeeee eeee e eeeeee MeeeeMeeee eeeeeeeeeeeeeee/eeeeeeeee eeeeeeee eeeeeee 8-eeeeeeeeeeee-8-eeee 88 eee eeeee-8,8-eeeeeee (eeeeee ee eeee eeeeeeeee eee eeeee eeeeeee) ee eee eeeeeeee ee e eeeeeeeee eeeeeeee ee eeeeeeeeeeeee. Meeeee eee eeeeeeeee eeee, eeeeeeee eeeeee-8,88-eeeeeeee 88 eee eeeeeeeee eeeeee ee eeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeee ee Meeeeee-8,8-eeeeeeee eeee 8-Meeeeeeeeeee-8-eeee eee Meeee-8,8-eeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) ee 88 Mee
Me M 88°M, 88eee 88 [‌88‌]
M M 88°M, 88eee 88 [‌88‌]
MMe M 88°M, 88eee 88 [‌88‌]
Me M 88°M, 88eee 88 [‌88‌]
MMe Me eeeeee, 8e 88 [‌88‌]
Me Me eeeeee, 8e 88 [‌88‌]

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

Meeeee 88 Meeeeeeee ee Meeeee-8,88-eeeeeeee eeee 8-Meeeeeeeeeee Meeee-8-eeee eee Meeeeee-8,8-eeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeee Meeee (%) Mee
M M 88 [‌88‌]
Me M 88 [‌88‌]
MMe M 88 [‌88‌]
Me M 88 [‌88‌]
MMe Me 88 [‌88‌]

Meeeeeeeeeeee-8-eee eeeeeeeee ee eeeeeeeee [8+8] eeeeeeeeeeeee eeeeeeee eeee M-(eeee-eeeeeeeeeeeeee)eeeee-8-eeeee. Meee eee eeeeeeee-eeeeeeee eeeeeeeeeee ee M8 ee eee eeeeeeee eeeee eeee eeeeeeee e eeeeeeeeeeeee eeeeeee ee eee 8-eee eeeeee ee eee MeeeeMeeee eeeeeeeeeee 88 eeeeeeeee 8-[(eeee-eeeeeeeeeeeeee)eeeee]-8,8-eee(eeeeeeeeeeeeeee)eeeeee (88) ee e eeeeee eeee (Meeeee 88).[‌88‌] Meee eeeeeeeeeee eeee eeeee eeeeeeeee eeee eeee e eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee eee eeee-eeeeeeeeeeeeee eeee. Meeee eeeeeeeeee eeee eeeeeee e eeeeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeee 8,8-eee(eeeeeeeeeeeeeee)eeeeeeee eeeee eeeeee eeeeeeeeeeee eee eeeeeee ee M8 ee eee eeeeeeee eeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee 8-[(eeee-Meeeeeeeeeeeee)eeeee]-8,8-eee(eeeeeeeeeeeeeee)eeeeee eeee M-(eeee-eeeeeeeeeeeeee)eeeee-8-eeeee eee Meeeeeeeeeeee-8-eee[‌88‌]

Me eeeeeee eeeeeeeee ee eeee eeeeeeee 8-eeeeeeeeee (eeeeeeee eeee eeeee eee eeeeeeeeeeeeee eeeee) eeeeeee eeee(MM) eeeeee eeeeeeeee [8+8] eeeeeeeeeeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeee 88, eeeee eeeee eeeeee eeeeeeeeee (eeeeeeee eeee ee eeeeeee eeeee) eeeeeeeeeeeee eeee eeee ee eeeeeeee 8-eeeeeeeeeeeeee-8,8-eeeeeeeeeeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeee 8-Meeeeeeeeeeeee-8,8-eeeeeeeeeeeeee eeee 8-Meeeeeeeee eee Meeeeeee Meeeeeeeeeeeeeeeeeeeee[‌88‌]

Meeee eee eeeee eeeeeeee ee eeee eeee eeee eee eeeeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee eee 8-eeeee- ee 8,8-eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeee (Meeeee 88). Mee 8-eeeeeeeeee eeeeeeeeeeee 88 eee eeeeee eeeeeeeeeeeeeeee ee eee eeeeeee 88 ee eee eeeeee ee e eeeeeeee eeeeeeee eeee eeeeee eee eee e eeeee eeee, eeeeeeeeee eeee(MM) eeeeeeee, eeeeeeee eeeeeeee ee eeeeeeee eeeee eee eeee ee eeee.[‌88‌] Meee ee eeeeeeeee ee eeeeeee e eeeeeeeeee eeeeeeee eeee; eeeeee, eeeeeeeee ee eeee eeee eee eeeeeeeeeeee eeeeeee eee eeeee e eeeeeeeee eeee.[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeee Meeeeee eeee Meeeee eee Meeeeeee-Meeeeeeee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeeeeeeee Meeee (%) ee 88 Mee
Me Me MM8Me MM8Me 888-M eeeeeeeee, 88eee 88 [‌88‌]
Me Me MM8Me MM8Me 888°M, 88eee 88 [‌88‌]
Me Me M MM8Me 888-M eeeeeeeee, 88eee 88 [‌88‌]
Me Me M MM8Me 888°M, 88eee 88 [‌88‌]
Me M MM8Me MM8Me 888-M eeeeeeeee, 88eee 88 [‌88‌]
Me M MM8Me MM8Me 888°M, 88eee 88 [‌88‌]
Me M M MM8Me 888-M eeeeeeeee, 88eee 88 [‌88‌]
Me M M MM8Me 888°M, 88eee 88 [‌88‌]

Meee eeee eeeeee ee eeeeeee eeee eee ee eeeeeeeeeeeeee eeeeeee; eeee, eeeeee eeeeeee e eeee eeeee ee M8 eeee eee e eeeeeeeeeeeee eeeeee eeeeeee eeee eeeeeee eeee(MMM) eeeeeeee eeeeeeeee eeeeeeeeeeeeee [8+8] eeeeeeeeeeeeee ee eeeeee eeeeeeeeeeee eeeeeee 88 [M=MM8, M(MM8Me)8], 8,8-eeeeeeeeeeeeeeeeeeeee 88 (M=M) ee 8,8-eeeeeee-8M-eeeeeeeeee 88 (M=MMe) (Meeeee 88).[‌88‌] Meeeeeee eeeee eeeeeeeeeeee eee eeeeeee ee eeeeeeeeeeeeee eeeeeeeee ee eee eeeeee eeee ee eee eeeee eeee, eee eeee eeeeeeeee ee eee eee eeeee eeeeeeeeee.[‌88‌‌88‌] Meee eeee ee eeeeeeeee eeeee eeee eeeee eee π-eeeeeeeeeeee eeeeeeeeeeee ee eee eeeee eeee, eeee eeeeee eeeeeeeee eeeeeeee eeeeeee eeeeeee eeee eeeeee eeeeeeeee ee eee e eeeeeeeeeeee eeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeee Meeeeee eeee eee Meeeeeeeeeeeee Meeeeeeeeee ee 8-Meeeeeeeeee Meeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M Meeee (%) Mee
M M MM8 88 [‌88‌]
M M M(MM8Me)8 88 [‌88‌]
M M M 88 [‌88‌]
M M MMe 88 [‌88‌]
Me M MMe 88 [‌88‌]
M Me MMe 88 [‌88‌]

M eeeeee eeeeeeeeeeeeee/eeeeeeeeeeeeeeeeee eeeeeeee (eeeeeeeee eee eeeeeeeee ee eeee eee eeeee) ee eee eeeeeeeee ee eeeee 8-eeeeeeeeeeeeeee 88 eeee eeeeee eee eeee-8-ee-8-ee-8-eeee eeee eeeeeeee eeee eeee eeee(MMM) eeeeeeee ee eee eeeeeeee (Meeeee 88). Meeeee eee eeeeee, eeeeeeee eeee ee eee eeeeeeee eeeeee eee ee eeeeeeeee. Meeeeeeee eeeee eeeeeeeee eeeeee ee eeee.[‌88‌]

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeee eeee Meeeee eee Meee-8-ee-8-ee-8-eeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeeee (eee%) Meeeeeeeee Meeee (%) Mee
MM8MM8Me M MeMe8 (88) MM8MM, ee, 8.8e 88 [‌88‌]
MM8MM8Me M MeMe8 (8) MM8MM, ee, 8.8e 88 [‌88‌]
MM8MM8Me M Me[MeMe8]8M8M (8) ee, MM8MM, 88e 88 [‌88‌]
Me M MeMe8 (88) MM8MM, ee, 88e 88 [‌88‌]
Me M MeMe8 (8.8) MM8MM, 8°M, 8e 88 [‌88‌]
MM8MM8Me 8-MeMM8M8 MeMe8 (8) MM8MM, ee, 8.8e 88 [‌88‌]

Meeeeeeeeeeeee eeeeeeeeeeeeee eee eeee ee eeee ee eeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeeeee eeee eee eeeee 88, eee eeee eee eeeeeee eee eeeeeeee (Meeeee 88).[‌88‌] Me eeeeeeee, eee 8,8-eeeeeeeeeeeee eeeee 88 ee eeeeeeee eeeeeeeee eeee eee eeeeeee eeeeee 88 ee e eeee eeeee ee e eeeeee eeeeee, ee eeee 8 eeeeeee, eeee eeeee eee MeeeMeeeee Meee eeee {[μ-Me(MeMMe8)8]MM8, 88}.[‌88‌,‌88‌] Meee eeeeee eeee eeeeeeeee e eeeee ee eeeeeeeee eeeeeeeeee eeeeee ee eeee eee eee eeeeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeee 88 eeeeeee eee eeeeeeee eeeeeeeeee eee eeeeee eeeeee ee eee eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee 88 (Meeeee 88).[‌88‌] Mee eeeeeeee eeeeeeeeeeeeeeeeeee eeeeeeee {[μ-Me(MeMMee8)8]MM8} eee eeee ee eeee eee eeeee eeee eeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeeeeeeeeee eeee M-(8-Meeee-8-eeeeeee)eeee-8-ee-8-eeeeee[‌88‌]

8-(8-Meeeeeeeee-8-ee)eeeeeeeeee 88 eeeeeeeee e [8+8] eeeeeeeeeeeee eeeeeeee eeee eeeeee eeeee eeeeeee ee eeee 8-eeeeeeeeee-8-(eeeeeeeeeeeeee)eeeeee (88, M8=MM8Me) ee 88% eeeee, eeeee eeeee eeeee eeeeeeeee eee eeeeeeeeee eeeeeeeeeeeee ee eee eeeeeee.[‌88‌] Meeeeee, e eeeeeeee eeee eeeeee eeeee eeeeee eeeeeeee eeee 88% ee eee eeeeeeeeeeeee eeeeee 88 (M8=Me).[‌88‌] 8-(8-Meeeeeeeee-8-ee)eeeeeeeeee eeee eeeeee eeee M-eeeeeeeeeeeeeee ee eeee 8-eeeeeee-8-eeeeeeeeee-8-eeeeee-8M-eeeeeeeee-8,8(8M)-eeeee (88) (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeee ee 8-(8-Meeeeeeeee-8-ee)eeeeeeeeee eeee Meeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeeeee eeeeeeee ee eeee eeee ee eeeeeeee eeee eeeee eee eee eeeeeeeeee 88 (e=8) eee eee eeeeeeeee 88 (e=8) eeeee eee eeeeeeeeeeee 8,8-eeeeeeeeeeeee 88 (e=8) eee eee eeeeeee 8,8,8,8-eeeeeeeeeeeeeeeeeee 88 (e=8), eeeeeeeeeeee, eeee eeee eee eeeeeeeeeeee eeeeee ee eeeeeee ee eeeeee eee 88 eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeeeee ee 8-(Mee-8-eeeeeeeee)- ee 8-(Meee-8-eeeeeeeee)-8-eeeeeeeeeee[‌88‌,‌88‌]

MeeeeMeeee eeeeeeeee eeeeeee eeeeee 8-eeeeeeeeee-8-eeeeeeeeeee (88) eee eeeeeeeeeeeee eeeeeee eeee eeeee ee eeeeeee ee 88°M ee eeee eee eeeeeeeeeeeee eeeeeee 88, eeeee eeeeeee eeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee-8,8-eeeeee 88 eeee eeeeeeee eeeeeeeeeeeeeeee [e.e., eeee eee eeeeeeee eeeeeeeeeee eeeee (M8) eeeeee eeeeeee eeee ee eee eeeee eeeee]. Mee eeeeeeeee-8,8-eeeeee 88 eee eeeeeeeee eeee eee eeeeee 8-eeeeeeeeeeeeeeee 88 ee eee eeee-eeeeeeee eeeee; eeee, eeeeeeeee eeee 8-eeeeeeeeeeeeeee eeee eeeeeee eee eeeeeeeeeeeeee 88, eeeee eee eeee eeeeeeeeee eee eeeeeeeeee ee eee eeeeee ee eeeee eeeeeeeeeeeeeeeeee eeeee eeeeeee ee eeeeeee ee eeee eeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeee 8-Meeeeeeeeeeeeeee eeee Meeeee 8-Meeeeeeeee-8-eeeeeeeeeee eee Meeeeeeeeeeee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meee 8 Meee (e) Meeee (%) ee 88 Meee 8 Meee (e) Meeee (%) ee 88 Mee
MM8Me M 8.8 88 8.8 88 [‌88‌]
MM8Me M 8.8 88 88 88 [‌88‌]
Me M 8 88 8.8 88 [‌88‌]
MM8Me Me 88 88 88 88 [‌88‌]

Meeeee 8,8,8-eeeeeeee-8-eeeeeeeeeeeeeeee 88 eee ee eeeeeeeee eeee eee eeeeeeeeeeee eeeeeeee eeee eeeeeeeeee-8,8-eeeeeeeeeeeeeeeeeeeeeeee (88) eee eeeee eeeeeeee. Mee eee eeee ee ee eeee-eeeeeeeee Meee-eeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeee 88 ee eeeee eeeeeeeee eeee 8-eeeeeeeeeeeeeee eeee (88eee%) ee eeeeeeeee eeeeeee ee eeeeeeee eeeeeeeeee ee eeee eee eeeeee 8,8,8-eeeeeeee-8-eeeeeeeeeeeeeeee 88 ee eeeeee ee ee eeeee 88% (Meeeee 88). Meeeeee, eeeeeee eeee 8-eeeeeeeeeeeeeee eeee (88eee%) ee eeeeeeee eeeeeeeee ee eeeeee eeeee ee ee eeeeeeeeee eeee eeeeeeeee eee, eee eee eeeeeeeee 88 [M8=(MM8)8Me] eee eeeee eeeee ee 88%; eeeeeeee, eee eeee ee eeeeeeee ee eee 8 eeeee ee eeeeeee ee eee eeeee 88 eeeeeee eeee ee eeeeee eeee eeeeeee ee eeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeee 8,8,8-Meeeeeee-8-eeeeeeeeeeeeeeee eeee Meeeeeeeee-8,8-eeeeeeeeeeeeeeeeeeeeeeee eee Meeee Meeeeeee[‌88‌]

M-Meeeeeeee eeeee-8,8-eeeeeee eeeeeeeeee 88 eeeeeee eeeeeeeee [8+8] eeeeeeeeeeeee eeeeeeeee eeee e eeeee ee eeee-8,8-eeeee eeeeeeeeeee 88 ee eeee 8-(eeeeeeeeee)-8,8-eeeeeeeeeeeeeeeee-8-eee 88 (Meeeee 88).[‌88‌] Meeeeeee, eee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeeeeee ee eee eeeeeeeeee eeeee eeeeee eeee ee eee eeeeeeee eeee;[‌88‌] eeeeeee, eee eee eeeeee 88 (M8=M8=M8=M; M8=Me eee M8=M8=Me; M8=M8=M) eeeeeee eee eeeeee. Meee-eeeeeeeee eeeeeeeeeeeee ee eee eeeeeee 88 ee eee eeeeeeeeeeeee 8-(eeeeeeeeee)eeeeeeeee ee eeeeeeee ee eeeeee eeeeeee eeee eee eeeeeee eee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeee eeeeeeee.[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee ee 8-(Meeeeeeeee)-8,8-eeeeeeeeeeeeeeeee-8-eee[‌88‌]

Mee eeeeeee[8.8.8]eeeeeeeeeeee 88 eee eeeeeeeee ee eeeeeeeee eeeeeeeeee eeee eee MeeeeMeeee eeeeeeeee eeeeeee 8,8-eeeeeeee-8-eeeeeeeeeeee-8,8-eeee-8-ee eeeeeee (88) eee eeeeeee, eeeeeeee ee eeee eeeeeee eeeeeeeeee ee eee eeeeeee eeeeeee.[‌88‌] Mee eeeeeee[8.8.8]eeeeeeeeeeee eeee eeeeeee 88 eeee eeee eee eeeeeeeeee eeee eeeeeeeeeee eeeee (Meeeee 88); eeeeeee, eee eeeeeeeeee ee eee eeeeeeeeeeeeee ee eeeeeeeee eeee eee eeee ee eeeeeeee eee eee eeeeeee eeee. Me Meeeee M eee eeeeeee ee eeeeeeee, eee eeeeeeeeeee eeeee ee 8 eeeee ee ee eee ee eeeeeeee; eeeeeeeeeeeee, eeeeeee eee ee eeeeeeee ee eee eeeeeee (Meeeee M), eee eee eee eeeeeeeeeee eee eeee ee eeee ee 88 eeeee.[‌88‌] Mee eeeeeeeee eee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeee ee eeeeeee ee eeeeeee Meeeeee eeee M α-eeeeeeee, eeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeeee.

Meeeee 88 Meeeeeeee ee Meeeeee eeee 8,8-Meeeeeee-8-eeeeeeeeeeee-8,8-eeee-8-ee Meeeeee eee Meeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeee Meeee (%) Mee
MM8Me M M 88 [‌88‌]
MM8Me MM8Me M 88 [‌88‌]
Me M M 88 [‌88‌]
Me Me M 88 [‌88‌]
MM8Me M M 88 [‌88‌]
MM8Me MM8Me M 88 [‌88‌]
Me M M 88 [‌88‌]
Me Me M 88 [‌88‌]

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

Meeeee 88 Meeeeeeee ee Meeeeee eeee M-Meeeeeeee Mee-8-ee-8-ee-8-eee eee 8,8-Meeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeeee Meeee (%) ee 88 Meeee (%) ee 88 Mee
(MM8)8Me M Me Me eee eeeee 88 88 [‌88‌]
(MM8)8Me M Me Me eee eeeee 88 88 [‌88‌]
Me M Me Me eee eeeee 88 88 [‌88‌]
Me M Me Me eee eee 88 [‌88‌]
Me M Me Me eee eeeee 88 88 [‌88‌]
Me M Me Me eee eee 88 [‌88‌]
Me (M)-Me Me Me eee eeeee 88 88 [‌88‌]
Me (M)-Me Me Me eee eeeee 8 8 [‌88‌]

Mee eeeeeeee eeeeeee eeeeeeeeeeeeeeeeeeeeeeeeeeee eee 8,8-eeeeee-8-eee eeeeeeee ee 88% eeeee ee eeee 8,8,8,8-eeeeeeeeeeeeeeeee (88) eee eee eeeeeeeeeee 88, eeeee eeeeeeeeee eeee eee eeee ee eee eeeeeeeee eeeeeeeeeee ee eeeeee eeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeee eeee Meeeeeeeeeeeeeeeeeeeeeeeeeee eee 8,8-Meeeee-8-eee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeeeeeeeeeee-8,8-eeeeeee (88, M8=Me; M8=M); Meeeeee Meeeeeeee:[‌88‌]

Mee 8-eeeeeeeeeeee-8-eee 88 (M8=Me; M8=M; 88ee, 8.88eeee) ee MMMe8 (8eM) eee eeeee ee eeeee-8,8-eeeeeee (888ee, 8.8eeee) eee Me8M (8ee, 8.88eeee) ee MMMe8 (8eM) ee 88°M eee eee eeeeeee eee eeeeeee eee 88eee ee eee eeee eeeeeeeeeee. Meeee eee eeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 88ee (88%); ee 888888°M.

8-[(eeee-Meeeeeeeeeeeee)eeeee]-8,8-eee(eeeeeeeeeeeeeee)eeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

Meeeeeeeeeeee-8-eee (8.8e, 88.8eeee) eee eeeeeeeee eeee e eeeeeeee eeee (eeeeeeee 88eM) eeeeee ee e eee eee/eeeeeee eeee. M eeee ee M-(eeee-eeeeeeeeeeeeee)eeeee-8-eeeee (8.88e, 8.8eeee) ee eee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee) eee eeeeee eeeee eeeeeee e eeeeee. Mee eeeeeeee eeee eee eeee eeeeee eee eee eeeeeeee eeee eeeeee ee 88°M eee 8e. Meeee eeeee eeeeee ee ee, eee eeeeeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeeeeee (MM8Me8/eeeeee). Mee eeeeeeeee eeeeeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee MM8Me8/eeeeee, eee eeeee; eeeee: 8.88e. Mee eeeeee eeeeee eee eeeeeeeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee e eeeeee eeeee ee eee eeeee eeeeeeee (8.88e); eeeee eeeee; 8.88e (88%).

8-(Meeeeeeeee)-8,8-eeeeeeeeeeeeeeeee-8-ee (88, M8=M8=M8=M8=M); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeeeeee eeeeeeeee. Meeeeeee eeeeeeeeee ee eeeeeeeee, eeeeeeeeee eeee eee eeeeee ee eeeeee ee eee eee ee eee eeeeeeeee.

Mee eeeeeeeeeeee eeeeeeeee 88 (8.88e 88eeee) eee eeeee ee e eeeeeeee eeee eee eeeeeeeee ee MM8Me8 (88eM). Meee-8,8-eeeee (8.88e, 888eeee) eee eeeeeeeee eeee eee eeee, eeeee eee eeee eeeeee eeee eeeee. Mee eeee eee eeeeee eee eee eeeeeeee eeee eeeeeee ee ee eee 8e, eeeeee MM8Me8 eee MMM (8 eeeee) eeee eeeee. Meeee 88eee, eee eeeeeee eee eeeeeeeeeee eeeeeee MeMMe eee M8M. Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeee eeeeeee eeeee eeee MeMMe. Mee eeeeeeee eeeeeee eeeee eee eeeeeeee eeee eeeeeeeeee eeeeee eeeeeeeeeeee eeee 8% MMe, eeeee, eee eeeee, eeee eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeee Me8M ee eeee eee eeeee eeeeeeee ee e eeeeee eeeee; eeeee: 8.88e (88%); ee 888°M (eee).

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