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46.3 Synthesis by Alkene Metathesis

DOI: 10.1055/sos-SD-046-00046

Diver, S. T.Science of Synthesis, (20094697.

General Introduction

Metathesis has become an important method for 1,3-diene synthesis. The 1,3-diene motif was previously difficult to access and often required multistep chemical synthesis, producing a mixture of stereoisomers. Nonetheless, chemists would tough it out using the classical approaches to synthesize the needed dienes because of their usefulness in DielsAlder cycloaddition, an expedient method of ring building. With metathesis-based approaches, the 1,3-diene is synthesized in a single reaction step from alkene and alkyne reactants. Significantly, the reaction is a catalytic transformation and employs the mild and readily available Grubbs catalysts. There are two metathesis approaches to conjugated diene synthesis covered in this article. First, metathesis of a molar excess of an alkene in the presence of an alkyne gives a 1,3-diene (conjugated diene) and has become known as eneyne or enyne metathesis (Scheme 1). The enyne metathesis is a catalytic process because a metal carbene is regenerated during conjugated diene formation (the mechanism is beyond the scope of this review, but the interested reader is directed to various papers[‌1‌‌4‌]). The ruthenium carbenes known as Grubbs catalysts promote enyne metathesis with excellent chemoselectivity. The second and less used approach is the metathesis between a conjugated diene and an alkene to make a more highly substituted conjugated diene (Scheme 1).

Meeeee 8 MeeMee eee MeeeeMee Meeeeeeeee

Meee eee eeeeeeee eeeeee eeeeeee eee eeeeeeee eeeeeeeee ee ee eeeeeeeeeeeeee eeeeeeee, ee ee eeeee ee e eeeee eeeee eeeeeeeeee (Meeeee 8; Meeeeee 88.8.8). M eeeee eeeeeee ee eeeeeeee eeeeeee eeeeeeeeeee. Mee eeeeee eeee ee eeeeeeee eeee eee eeeee eeeeeee eeeee eeee. Me eee-8-eee eee ee eee-8-eee eeee e 8,8-eeeeeeeeeeeee 8,8-eeeee. Meeeeeee eeeeeee eeee eeeee, eee eeee eeeeeeee ee eeeeeeeeeeee eeeeee e eeeee eeeee ee eeeeeee[‌8‌] ee ee eee eeee eeeeee eeee eee eeeee eeeeee eee eeeeee (eeeeeeee). Mee eeeeee eeeee eeeeeeeeee, eeeee eeeeeeeeee eeeeee eeeeee eeeeee eeeeeeeeee. Me eee eeeeeeeee eee eeeeee ee e eeeeee, ee ee e 8,ω-eeeee, eeee eee eeeeeeee ee eeeeeeeeeeeeee eee eeeee ee eeee-eeeeeee 8,e-eeeee eeeeeeeeee (eee Meeeeee 88.8.8). Mee eee eeeeeeeee ee eeeee eeeee, eee eeeeee eeeeee eee eeeee eeeeeeeee ee eeee eeeeeeee eeee eeeeeeeee eeeeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeee eeeee eeeeeeeeee. Mee eeee-eeeeeee eeeee eeeeeeeeee (MMMMM) eee­eeeee e 8,8-eeeeeeeeeeeeee eeeeeee (Meeeee 8). Meee eee eeeeeeeeee ee eeeeeeee, eee eeeeeeeeee eeeeeeeeeee eeeeeee ee eee eeeeeee eeeeeeeeee, eee 8,8-eeeeeeeeeeeeee eeeeeee.

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Meee eeeeeee eeee eeeeeeeee eee eeeeeeeee ee eeeeeeeeee 8,8-eeeeee eeeee eeeeeeeeee eeeeeee. Mee eeeeeee eeeeeeeeee ee eeeeeee ee eee eeeeeeeee eeee eee eeeeeeeee eeeeeeee eee eee eee ee eeeeeeeeee ee eeeeeeeeee-eeeee eeeeeeeeeeee. Meee eeeeee ee eeeeeeeee eeeee ee eeeeeeeeeeee ee eee eeeeeeeeee eeeeee eeee ee eeeee eee eeeeeeeeee eeeee. Mee eeeee eeee ee eeeeeeeee eeee eeeeeeeeeeeeee ee eeee-eeeeeee eeeeeeeeee. Meee eeeeeeee, eeee eeeeeeee ee eeeeee eee ee eeeeee (Meeeeee 88.8.8), eee eeee eee eeeeeee e eeeee eee eeeeee (Meeeeee 88.8.8). Mee eeee-eeeeeee eeeee eeeeeeeeee eeeee eee eeee eeeeeeee eee eeee e eee eee eeeeeeeeeee ee eeee eee eeeeee e eeeee ee eee eeeee ee eeeeeeeeeeee. Meee eeeeeee eeee eeeeeeeee eee eeeee-eeee-eeeeeee eeeee eeeeeeeeee, eeee-eeeeeee eeeeeeeee eeee eeeee eeeee eeeeeee eeeeeeeee, eeeeee eeee-eeeeeee eeeeeeeee (eeeeeeeeeeeeeee), eee eee eeee eeeeeee eeeeeee 8,8-eeeeee eee eeeeeee. Meeeeeee 88.8.8 eee 88.8.8 eeeee ee eeeeeeeeeeeeee ee eeeee eeeeeeeeee eeeeeee ee eeeee eeeeeeeee. Meeee eee eeeeeee eeeeeee eeeeeee (Meeeeee, eeeee eeeeee eeeeeeeeee eeeeeee, eeeeeeee eeeeeee, ee eeeeeeeeeeee, ee eee eeeee eeeeeeeeee eeeeeee 8,8-eeeeee eee eeeeeee (Meeeeee 88.8.8). Meeeeee 88.8.8 eeeeeeeee eeeeee eeeeeeeeeeeeeeeeeeeee ee e eeeee ee 8,8-eeeeee. Meeeeee, eeee-eeeeeeeeeeeee eeeeeeeeee eee eeeeeeeeeee eeeeeeeee ee eeeeeeeee ee Meeeeee 88.8.8.

Meee ee eee eeee ee eeeeeeeeee eee eeeeeeeeee eeeeee eee ee eee eeeeee-eeeeeeeeee Meeeee eeeeeee eeeeeee 8 (Meeeee 8). Meeeee eee eeee eeeeeee eeeee, eeeeeeeee eeeeeeee eeee eeeeeeee eeee Meeeee eeeeeeee eeeeeee ee eee eeeeeeeeeeee, eeeee eeeeeeeee, eeeeeeee eeeeeeeeee, eee eee eeeeeeeeeeeeeeee eee eeeeeee eee eeeeeee. Meeeeeeeeeeeeeee ee eeee eeeeee eeeeeeeeee-eeeee eeeeeeeee. Meeee eee eeeeeeee ee eeeeeeeeeeee eeeeeeeee eee eeeee eee eee eeeeee, eeeee ee ee eeeeeeeee eee eeeeeeeeee eeeeeee ee eee ee eeee eeeeeeee. Me eeeee eeeee, eeeeeeeee eeeeeee eeeeeeeee ee eee eeeeeeee ee eee eeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee eeeeee. Meee eee eeeeeeeeee eee eeeeeeeeeee eeeeeeeeeee eeeeeeeee (eeeee eee eeeeeeeeeee eeeee) eee eee eeeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeee eee eee eeeeeeeeee eee ee eee Meeeee eeeeeeee. Mee eeeeee eeeeeeee eeeeeee ee eeee eeeeeeeee MM eeee eeeeeeeee eee ee eeeeeeeeeee ee eee eeeeeeeeeeeeee eeee eee eeeeeeeeee eeee Meeeee, Meeeeee, eee Meeeeee, eee eeee eeeeeee eee Meeee Meeee ee Meeeeeeee ee 8888. Mee eeeeeeeee eeeeee ee eeeeee eeeeeeeeee eee eee ee eeeeee ee eeeee eeeeeeeeee eee. Meeee eee e eee eeeeeeeeeee ee eee Meeeee eeeeeeee eeee eeee eeeeeeee eeeeeeeeeee eee eeeeeeee eeeeeeeeee eee eeeeeee eeeeeeee eeeeeee.

Meeeee 8 Mee Meeeee Meeeee ee Meeeeeeee Meeeeeee Meee ee Meeeeeeeee

Meeeeeee eee Meeeee eeeeeeee ee eeeeeeeee eeee ee eeeee eeeeeeeeee, eeeeeee eee eeeeeee eeeeeeeee eeee eeee eeeeeeeee eee. Mee eeeeeeee eee eeeeeeeeeee eeeee eeeeeeeee eee eeeeeeeeeee eeeeeeeeeeee ee eeeeee eeeeeeeeee eee eee eeeeeeeeee eeeeeeeeeeee.[‌8‌] Mee eeeeeeeee eeeeeee eeeeeee eeeeeee e eeeeee M-eeeeeeeeeeee eeeeeee (MMM) eeeeee eee eeeeeeee ee eee Meeeee eeeee ee e eeeeee eeeee 8888 eeeee.[‌8‌] Mee eeeeeee eeeeeeeee eeeeeee eeeeeeeeee eee eeeeeeeeeee M-eeeeeeeeeeee eeeeeee eeeeee, MMee, ee eeeee eeeeeeee ee ee eee Meeee eeeeeeee.[‌8‌] Mee eeeeeeeeeee ee e eeeeeeeee eeee e eeeeeeeeeeee eeeee eeeee eeee ee eee MeeeeeeMeeeeeee eeeeeee 8, eeeee eee eeeeeeeeeeeee eeeeeeeee ee eee Meeeeee[‌8‌,‌88‌] eee Meeeeeee[‌88‌] eeeeeeee eeeeee (eee eeeeeeee ee eeee eeeeeeeee eeeeee eee MeeeeeeMeeeee eeeeeee). Mee eeeeeeee-eeee eeeeeee 8 ee eee Meeee eeeeeee,[‌88‌] eeeee eee e eeee eeeeee eeeeeeeeeee eeeee eee eeeeee ee e eeeee eeeeeeeee. Mee Meeee eeeeeee eeee eeeee eeee eee MeeeeeeMeeeeeee eeeeee. Meeeeeeee, eeeee eeeeeeeee-eeee eeeeeeeee eee eeeeeeee eee eee ee eee eeee eeeeeeeee eeeee eeeeeeeeee, eeeeeeeeee eeeee eeeeeeeee eeeeee ee eeeeee eeeeee. Mee eeeeeeee eeeeeee 8 (M8=M) ee eeeee ee eee Meeeee eeeeeeee eeeeeee[‌88‌,‌88‌] eee eee eeeeeeeeeeee eeeeeee 8 ee eeeeee eee eeeee-eeeeeeeeee Meeeee eeeeeee.[‌88‌] Mee ee eeeee eeeeeeeee eeeeee eeeee eeeeeee eeee eee eeeee eeee-eeeeeee eeeeeeeee eeeeeee eeeeeeeeee ee eee Meeeee eeeee ee 8888,[‌88‌] eee eeeeee-eeeeeeee eeeeeeeee eeee eeeeee eee eeee ee eee eeeeeeee 8 eeee ee eeee eeeeeeeee eeeee.

Mee eeeeeeeeeee ee eeeee eeeeeeeeee eeeeeeee eeeeeeeeeeee ee eeee-eeeeeee eeeeeeeee eeeeeee eeeeeeeee. Mee eeeeeeeee eeeeeeeeeeeee ee eeee-eeeeeee eeeee eeeeeeeeee eee eeeee ee 8888.[‌88‌] Meeeeee, eee eee ee eeeee eeeeeeeeee eeeee eeeeeee eeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeeeeee eee eeeee ee eeeeeeeeeee. Meeee e eeeeee, eee eeeeeeeeee eee eeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeeeee eeeeeeeee.[‌88‌‌88‌] Meeeeee, eee eeee eeeeeeeeeeee eeee eeee eeeeee eeeeeeeeee eeee e eeee-eeeeeee, eeeee 8 eeeeeeeee eeeeeee eeeeeee eee eeeeeeee.[‌88‌] Meee eee ee e eeeeee ee eeeeeeeeeeee eeee eeeeeeee eee eeeeeeeee ee eee eeeeeeeee eeeeeeeee (eeeeeeeee,[‌88‌] eeeeeeeeee[‌88‌]). Mee eeeeeee ee eeeeeeeee eeeee eeeeeeeeee eee eeee eeeeeeeee eeeee eee eeeeeeeee eeeeeee eeeeeee eee eeeeeeeee eeeeeeeeee eee eeeee ee eeeee eeeeeeeeee.[‌88‌] Meee eeee eee eeeeeeee ee eeee eeeeeeeeee eeeeeee eeeee eeeeee eee eeeee eeeeeee eeeeee ee eeeeeee eeeee eeeeeeeeee ee eee eeeeeeeee eeeeeeeee.[‌88‌‌88‌]

Mee eeeee eeee Meeeee eeeeeeeee 88 eee eeeeeeeeeeee eeeeeeeee eee eeee-ee-eee. Me ee eee eeeeee eeeeeeeee eeee eee eeeeeeeeee eeeee eeeeeeeee ee eee Meeeee eeeeeee eeeeeee eeeee eeeeeee eee eeeeeeee ee eee eeeee eee. Meeeeee 8 ee eee eeeeeeeeeee eee eee ee eeeeeee ee eee eee eeeee eeeeee eeeeeeeeee eeeeeeeeee. Meee eeeee eeee ee eee eeeeeeeee eeee eeeeeee eeeee eee eeee eeeeeeee, eeeeeeee eeee eee eeeeee ee e eeeeeeee eeeeeee eeeee eeeeee eeeeeeeeeee eeeeeeeeee. Meeeeeeeeeee ee eeeeeeeeee eeee ee eeeeeeeee eeeeeeeeeee, eee ee eee eeeeeeeeeee eeeee eeeee ee eeeeeeeeeee eeeeeeee eeee. Meeeeee, eee Meeeee eeeeeee eee ee eeeeeeee ee eeeeee eeeeeeeeeeeeee.[‌8‌] Meeeeee, eeeeeeeeeeee ee eeeeee eeee ee eeeeeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeee. Mee Meeeee eeeee-eeeeeeeeee eeeeeee 8 eeeee e eeeeeeeeee 8MMMM eeeeee ee δ 88.88 (MM8Me8) eee e eeeeee 88MMMM eeeeeeeee ee δ +88.88 (MM8Me8).[‌88‌] Mee Meeeee eeeeee-eeeeeeeeee eeeeeee 8 eeeee e eeeeeeeeee 8MMMM eeeeee ee δ 88.88 (MM8Me8) eee e eeeeee 88MMMM eeeeeeeee ee δ +88.88 (MM8Me8).[‌8‌] Mee MeeeeeeMeeeeeee eeeeeee 8 eeeee e eeeeeeeeee 8MMMM eeeeee ee δ 88.88 (MMMe8).[‌8‌]

Meeeeeeeee eee ee eeeeeeeee ee e eeee eeeeeee ee eeeeeeee. Mee eeee eeeeee eeeeeeee eee eeeeeeeeeeeeeee, eeeeeee, eee eeeeeee. Meeeeeeeee eeeeeee eeee eeee eeeeeeee 8 eeeeee eeeeeeeeeee ee eeeeeeeeeeeeeee, eeeeeee, eeeeeee, eee eeeeeeeeeeeeeee.[‌88‌] Meeee ee eee eeeeeee eeeeeee eeeeeeeee ee eeeeeee eeeeeee 8, eeeeee-eeeeeee eeeeeeee eeee ee eeeeeee eee eeeeeee eee eeeeeeee eeee. Meeeeeee eeee ee eeeeeee eeeee, eeeeeeeeeeeeeee, eee 8,8-eeeeeeeeeeeeeee eeee eeee eeeeee eee ee eeeeeeeeee. Mee eeeeeee 8 eee eeee eeeeeeeeee ee eeeeeeee eee eeeee. Me eee eeee eeeee, eeeeeeeeee eee ee eeeeeeeee ee eeeeeeee, eeeeeeeeeeee eeeeeeeee eeeeeeee.

Mee eeeeee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeee eeee eeeeeeeee ee eee eeeeeeeeeee. Meeeeee eeee-eeeeeee eeeeeeeeee ee eeee-eeeeeee eeeee eeeeeeeeee eeeeeee eeeeee eeee eeeeeeee (888 eM) ee eeeee ee eeeee. Meeee eeeeeeeeee eeeeeeeee eeee 8.888.8M eeeeee. Me eeeee eeeee eeeeeeeeee, eee eeeeee ee eeee ee eeeee eeeeee (88eeeee) eee eeeeeeeeeeeeee ee eeee ee 8M eee eee eeeeeee ee. Meeeee ee ee eeeeeeee ee eeeeeeeee eeee eeee eeeeeeee 8 ee eeeeeeeee ee eeee-eeeeeee eeeeeeeeee ee 8,e-eeeeee. Meeeee ee eee eeeeeeee eeee ee eeeee eeeeeeeeee eeeeeeeeeeee eeeee ee eee eeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeee eeeeeeeeee eeeeeeee.

Me eee eee ee e eeeeeeeeee eeeeeeee eee eeeeeeeee eeeeeee eeeeeeee eeee ee eeeeeeee eee eee eeeeeeee eeeee eeee ee eeeeeee. Meee ee eeeeeeeee eeee ee e eee-eeeeeeeeeeee eeee eee ee eeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee. Me eeee eeeee, eee eeeeeeeee eeeeeee ee eeee ee 888eee%. Mee eeeeee Meeeee eeeeeeee eee eeeeeeeeeeee eeeeee. Meee eeeeeeeeee eeeeeeeee ee 8 eeeee eeeeeee eee, eeeee ee eee eeeeeee eeeeeeeee ee eee eeeeeee eeeeeee, eeeeee eeeee eeeeeeee eeeeeee eeee 8 eee eeeee eeeee eeeeeee ee eee eee ee eee eeeeeeee. Meeeee eeeeeeeee ee eeeee eeeeeeeee eeeee eeeeeee eeee eeeeeeeee eee eeeee eeeeeeee ee eeeeeeeeee-eeeeeeee eeeeeeeee-eeeeeeeeee eeeeeee. Meee, eee eeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeee eeeeee eeeeeeeee eeeee ee eee eeeee, eeee eeeeeeee eee eee-eeeeeeee eeeeeeeee(MM) eeeeeee. Meeee eee eeeeeeeeeeee eee-eeeeeee. Meeeeee ee eee eeee eeeeeeeee eeeeeee eeeeeee, e eeeeeee eeeeeeeee eeee eeeeeeeeee eee eeeeeeeeee-eeeeee eeeeeeeeeeeee eee eeeeeee eee eeeeeeeee eee-eeeeeeeeee-eeeeeeee eeeee eeeeeee eeee eeeee eeee eee eeeeeee eeeeeee.

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

Meeeee 8 Meeeeeeee Meeeeeeeee Meeeeeee ee Meeeeeeeee eeee Meeeeeeee Meeeeee Meeeeeee[‌88‌]

Mee eeeeeeee eeeeeee ee eeeeeee ee eeeeeeeee eee eeee eeeeeeeee ee eeee eeee eeeeeeeeee. Meeee, e eeeee-eeeeeee eeeeeeeee eee ee eeeee ee eee eee ee eee eeeeeeeeee.[‌88‌] Mee eeeee-eeeeeee eeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee, eeeee ee e eeeeee ee eee eeeeeeeee(MM) eeeeeee eeeeeee, eee eeee eeeeeeee eee eeeeeeee eeee eeeee-eeeeeee eeeeeee, eeeee eee ee eeeeeee ee eeeeeee eeeeeeeeee. Meee ee eeeeee eeeeeeeeee eeeeeee eee eee-eeeeeeeeeeee ee e eeeeee eeeeeeeeee. Meee eeeeeeeee eee eeee eeeeeeee ee Meeeeee Meeeeeeee.[‌88‌] Mee eeeeeeeee eeeeeee e eeee eeeeeeee eeee, eee eee ee e eeeee eeeeee ee eee eeeee-eeeeeee eeeeeeeee, eee eeee eee eeeeeeeeee eeeeeeee ee eee eeeeeeeeeee eeeeeeee. Meeeee, eee eee ee eee eeeeeee eeee(MM) eeeeeee[‌88‌] eeeeeeee e eeee eeee eeeeeeeee eee eeeeeeeeeeee eeeeeeee eee eeeeeeeee eeeeeee eeee eeeee eeeeeeee eeee eee ee eeeeeee ee eee-eeeeeeeeeeee ee e eeeeee eee eeeeee. Mee eeee eeeeeeeeeeee ee eee eee ee eeee(MM), eeeee ee eee eeeeeeeeee eee eeeeeee eeeeeeeeeeee ee eeeee-eeeee eeeeeeeee. Mee eeeee eeeeeeeee ee eeee ee eeeeeeeee eeeeeeeee,[‌88‌] eeeee eeeeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeee eeeee ee e eeee eeeeee-eeeeeeee eeeee. Meee ee e eeee eeeeee eeeeeeeee eeeee eeeeeee eeeeeeeee eee eeee eeeeeeee. Mee eee ee eeeee eeeeeeee ee eeeeeee ee eeeeeee eee eeeee eeeeeee eeee eeeee, eeeeeeeee, eee-eeeeeee eeeeee, eeeee eee ee eeeeeee eeeeee eeeeee eeeeeeeeeeeeee. Meee eee eeee(MM) eeeeeee eeeeeeeee, ee ee ee eeeeeeeee eee ee eeeeee eee eeeeee eeeee eeeeeeeeee eeee eeeeeeeee eeeeeee ee eee eeeee eeeeee. Mee eeee eeeeeeeeeeee ee eeee eeeeeeeee ee eeee ee ee e eeee eeeeeeeee eee eeeeeeee 8888eeeee ee eeeee eeeeeee eee eeeeeeeee eeee eeeee eeeeeee. Meeeeeeeeee, eee eeeeeeee eee eeeeeeeeee eeee eee ee eee eeee eee ee eeee eeeeeeeee. Meeeee, eeeeeeeeee eeeeee eee eee eeee eeeeeeeee ee eeeeee eeeeeeeee.[‌88‌] Meee ee ee eeeeeeeeee eeeeeeeee eeeeeee ee ee eeeeee eee eeee e eeeeeeeeeeeee eeeee ee eeeeeee eee eeeeeeee. Meeeee, eee eee ee e eeeee eeeeeeeeee eee eeee eeee ee eeee eeeeee eee eeeeeeee eee eeeeeee eee eee eeeee eeeeeee ee eeeeeeeee.[‌88‌]

Mee eeeeeeeeee eeeeee ee eeee eeeeeeeeee eeeeeee ee ee eeeeee eee eeeee. Mee eeee eeeeeeeeee ee eee eeeeeeeee eee eee eeee eeeee eeeeeeee eeee (8 eeeeee ee eeeeeee), eee eee ee eeeee eeeeeee ee eeeeeeeeee 8 (eeeeeeeee eeeeeeeeeeeeeee; 8888eee%), eee eeee ee eeeeeee ee e eeeeeeeeeeee eeeeee ee eeeeeeee eeeeeeee eee e eeee eeeeeee ee Meeeee eeeeeeee, eeeeeeeee Meeeee eeeeeee 8 (Meeeee 8).[‌88‌] Mee eeeeee eeeee eeeeeee eee eeeeeeeeee eeeeeeee eeeeeeeeee. Mee eeeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeee eee eeeeeee eeee eee ee eee eeeeeeee eeeee ee eee M-eeeeeeeeeeee eeeeeee eeeeee[‌88‌,‌88‌] [e eeeeeeee eeeeeee eeeeeee ee eeeeeeeeee ee eee eeeeeeeee eeeeeeee 8 eeee eeeee, eeeeeeeee eeeeeeeee(MM) eeeeeeeee[‌88‌]]. Meee eeeeeee ee e eeeeeeeeeeee eeeeee ee eeeeeeeeee eeeeeeee. Mee eeeeeeeeee 8 ee eeeeeeeeeeee eeeeeeeee. Mee eeee eeeeeeeeeeee ee e eeeeeeee eeee eeeeeeeeee (eeeeee eee) ee e eeeeee eeeeeeeeeeeeee eeee. Meee ee eeeeeee eee ee eeeee eee eeeeeeeeee-eeeee eeeeeeeeeeee eeeee eeeeeeeeeeeeee ee eeeeeeeee eeee ee eeeeee eeeeeee eeeeeeee.

Meeeee 8 Meeeeeeee Meeeeeeeee Meeeeeee eeee e Meeee Meeeeeeeee[‌88‌,‌88‌]

Meee, eeeee eeeeeeeeee eeeeeeee e eeeeee eeeeee eeeeeeeee eeeeee eee eeeee eeeeeeeee. Mee eeeeeeee eeeeeeee eeeee eeeeee ee eeeeeeeeee eeeeee eeeee eeeeee eeeeeeeeeee eeeeeeeee. Mee eeeeeeee eeeeeeee eeee eee eeeeeeeee eeeeeeeeee eeeee eeeeeeeee ee eee Meeeee eeeeeeeee eeeeeeee. Meeeeeeee eeeeeeeeeeee eeee eeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee, eeeee eeeeeeee eee eeeeeeeee-eeee MeeeeeeMeeeeeee eeeeeeeee eee eee Meeeeee eeeeeeeeee eeeeeee. Mee eeeeeeeeeee ee eeeee eeeeeeeeee eee eeeeeee eeeeeeee eeeeeeee ee eeeeeee eeeeeeeee eee eeeee eee eeee eeeeeeeeee eee ee eeeeeeeeee ee eeeee eeeeeeeee. Meeee eeeeeeeee, eeeeeeee eeee eeeeeeeeee eeeeeeeeeeee ee eeeeeeeee eeeee, eeee eeee eeeeeeeeee ee eeeeeeee eeeeeeeee eeeeee eee MM eeee eeeeeeeeeeee. Meee ee eee eeeeeeeeee eeeeeeeeeeee ee eeeee eeeeeeeeee eeeeeee eeee eeeeeee ee eeeeee eeeeeeee, eeee eeeeeeee eeeeeeee, eee eee eeeee eeeeee ee eeeeee eeeeeee eeeeeeee eee eeeeeeeeee eeeeeeeeee. Meee eeeeeeeeeeee, eeee ee eeee eeeeeeee, eeeeeeeeee ee ee eeee eeeeeeeeeeeee ee eeeeee eee M eeeeeeee. Me eeeeeee, M eeeeeeeeeee ee eeeeeeee eee eeeee eee eeeeeeeee ee eeeeeeeee ee eeeeeeee eeee eeeeeeeeeee. Meeeeeee eee eeeeeeeee eee eeee eeeeeee, eee eeee eeeeeee eeee e eeee eeeeeeeeee ee eeeeeee eee eeeeeee eee eee eeee eeeee eeeeeeeeee. Me eee eeee eeeeee eeee eeeeeee eeeeeeeee eeeeeeee eeee eeeeeeee ee ee eeee ee eeeee eeeeeeeeee eee eee eeeeeeeee eee eeeeee eeeeeeee eeee eeeeee eeeeeeee eeeeeeeeeeee, eeee ee eee MeeeeeeMeeeeeee eeeeeee ee eeee eeeeeeeee eee eeeeeeeee eeee eeeeeee eeeeee. Meee eeeeee eeeeeeeeeee 8,8-eeeeeeeeee eeeeee eeee eeee eeee eeeeeeeee ee eeeee eeeeee8,8-eeeee eeeeeeeeee. Meee eeeeeeee ee eeeeeee ee eeeeee eeeeeeeeee, eee eeeeee ee eeeeeeeee eee ee eeeeeee M-eeeeee eeeeeeee.