0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
40.3 Product Class 3: Amine N-Oxides

DOI: 10.1055/sos-SD-040-00583

O'Neil, I.Science of Synthesis, (200940855.

General Introduction

Tertiary amine N-oxides possess the gross chemical structure 1, in which a tetracoordinate nitrogen is substituted with three alkyl or aryl substituents and is datively bonded to an oxygen atom (Scheme 1). The term amine N-oxide has been used in the literature to describe a variety of chemical structures. In this section only amine N-oxides in which the nitrogen is sp3 hybridized, and R1, R2, and R3 are equivalent to either an alkyl, functionalized alkyl, or vinyl group will be considered. Compounds either containing sp2-hybridized nitrogen atoms (heteroaromatic amine N-oxides) or in which R1 is hydrogen or a heteroatom such as nitrogen, oxygen, or sulfur will not be discussed.

Meeeee 8 Meeeeeeee ee Meeeeeee Meeee M-Meeeee

Meeee M-eeeeee eeee eeee eeeeeee eeeee eee eee ee eee 88ee eeeeeee.[‌8‌] Meee ee eee eeeeeee eeeeeeeeeeeeee eeee eeeee M-eeeeee eeee eeeeeeee ee e eeeeee ee eee eeeeeeeee ee eeeee eeeee M-eeeeee eeee eeeeee eeeeeee ee eeeee eeeeeeee.[‌8‌,‌8‌] Meeeee, eeeeeeeeeeeeee M-eeeee eee eeeee eeeeeeee eeee eee eeeeee ee eee eeeee Meeeeeeee eeeeeeee ee 8888,[‌8‌] eee eee eeeeeeeeeeee eeee eeeee ee ee eeeeeee ee eee eeeeeeee eeeeee, eeeee, eeeeeee, eee eee eeeeee ee eeee eeeeeeeeeee, eeeeeeeeeee, eee eeeeee eeeeeeeeeee.[‌8‌] Mee ee eee eeeeeee eeeeee eee eee eeeeeeeeeeeee ee eeee (ee eee eeeeeeeeeee) ee ee eeeeeeee ee eee eeeeeeee eeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeeee M-eeeee ee eeeeeeeeeeeeee.[‌8‌] Mee eeeee eeeeeeee M-eeeee, eeeeeee,[‌8‌] eee eeeeeeee ee 8888, eee ee eee eee eeeee 8888 eee eee eeeeeeeee ee eee eeeeeeeeee eeeeeeeeeee eeee eeee Meeeeeeeeee eeeeee[‌8‌] eeee eeeeeeee ee eee eeeee eeeeeeee. Meee eeee 888 eeeeeeeee eeeeeeeee eeeeeeee eee eeeeeeeee eeeee M-eeeeee eeee eeee eeeeeeee ee eeee.[‌8‌] Meeeeee, eeee eeeee eee eee eeeeeeeeee eeeeeee eee eeeee eeeeee eeee eeeeeeee eeeee. Meeeee eee eeeeeee ee eeeeeeeeee, eeeeeeeeeeee, eee eeeeeeee ee eee eeeeeee eeeeeeee, ee ee eeeeeeee eeee eee eeeee M-eeeee eeeeeee eee ee eeeeeee ee eee eeeeee eeeeeeee eeeee, ee eeeeeee eeeeeeeeeeeee ee e eeee eeeeee eeeeeeee eeeeee.

M eeeeee ee eeeeeeeeeeeeee eeeeeeee eeeeeeeeee eeee eeeeeeee eeeee M-eeeeee eeeee ee e eeeeee eeeeeeeeeee ee eeeee eeeeee eeeee eeeeee. Meee eee eeeee eeeeeeeeeee eeeeeeeee eee eee eeeeeeeeee eeeeeeee ee eeee- ee eeeeeeeeee. Mee eeeeeeeeeee eeeeeeeee ee eeeee M-eeeeee ee eeeeeeee ee eeeeeeeee eeeeeeeeeeeeee M-eeeee, eeeee eeeeeee ee. 8% eeeee eee eeeeee ee 88% eeeeeeee.[‌8‌] Meee eeeeeeeeeee eee eeeeeeeeee eeeeee eeee eeeeeeeeeeeeeeeee ee eeeeeee eeee eeee eeeeeeee ee eeeeeeeee eeeeeeeeeeeeee M-eeeee eeeeeeeee. Meeeeeee eeeee M-eeeeee eee eeeee eeeeeee ee eeeee, eeeeeeee, eee eeeeeee eeeeeee eeeeeeee. Meee eeeeeee eeeeeee eeeeeeeeee ee eeeeeeee eeeeeee eeeeeeee eeee ee eeeeeee.[‌88‌] Meeeeeee eeeee M-eeeeee eee eeeeeeeeeeee eeeeee eeeee eeee eeeee eeeeee eeeeeeee eeeeee, eeee eeeeeee eeeee eeee eeeee ee eeeeeee eeeeee eeeeeeeeeeeeeee eeeee. Mee eMe eeeeee ee eeeee eeeeeeeee eeeee eee eeeeeeeee ee ee ee eee eeeeee ee 88.[‌88‌]

Mee eeeeeeeee ee eeeeeeee eeeee M-eeeeee eee eee eeeeeee ee eeeeee eeeeee eee eeeeeeee eeeeeeeeee eee eeee eeeee. M eeeeee ee eeeeeeeeeeeee eeeeeeeeee eeee eeee eeeeeeee ee eeeee eee eeeeeeee eeeeee ee eeeee eeeeeeeee. M-eee eeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeee eeeeeeeeeee ee eee eeeeee eeee eee eee eeeee eeeeee eeeeeeeeeeee eeeeee eee eeeeeeee eeee. Mee MM eeee eeeeee eee eeee eeeeeeeeee ee ee eeeeeeee eeeeeeeeeee eeeee ee eeeeeeeeeeeeee M-eeeee.[‌88‌] Mee eeeee ee 8.88±8.88 Å, eeeee ee eee eee ee eee eeeeee eeeeee-eeee eeeee, eeeeeeeeee eeee eeeeeee ee MM eeee eeeeeeeee eeeeeeeeee ee M-eee eeeeeeeeeee. M eeeeeee ee eeeee M-eeeee eeeeeeeeee eeee eeee eeeeeeeeee ee M-eee eeeeeeeeeeeeeeee eeeeeee.[‌88‌‌88‌] Mee eeeeeeee MM eeee eeeeeeeee eeeeee eeee e eeeeeee eeeee ee 8.888 Å ee ee eeeee eeeee ee 8.88 Å.

Mee eeeeeeeeeeee eeeeeeee eeeeeeeeee eeee eeeee M-eeeeee eee eeeeeeeeee eeeeeee eeeeeeee eeeeeee ee eee eeeee M-eeeee eeeeee ee eeee eeeeeeeee ee M-eee eeeeeeeeeeeeeeee eeee. M-eee eeeeeee eeeeeeeeee ee eeeee eee eeeee M-eeeee eeeeee ee eeeeeeeeeeeeeeee eeeeeeee eeeeee ee eeeee,[‌88‌] eeeeeee,[‌88‌] eee (+)-8-eeeeeeeeeeee-8-eeeeeeee eeee[‌88‌] eeee eeee eeeeeeeee. Meeeeeee eeeeeee ee ee eeeeeeee eeeeee eeeeee ee eeeeeee ee eee eeeeeee eeeeeeeee ee (8-eeeeeeeeeeee)eeeeeeeeeeeee M-eeeee.[‌88‌] Mee M-eee eeeeeee eeeeeeeee ee eee eeeeeee eeeeee eeeeeee 8-eeeeeeeeeeeeeeee M-eeeee eee eeeee-eeeeeeeeeee-8,8-eeee[‌88‌] eeeeeeeeeeee eeee eee M-eeeee eeeeee eee eeeeeeeeeeeeee eeeeeeee eeee ee eee eeeeeeee eeeeeee eeeeeeee. Meeeeeeee eeeeeee eeee eeee eeeeeee eee ee eee eeeeeeeee ee eeeeeee- eee eeeeeeeee eeee eeeeeee M-eeeeee.[‌88‌‌88‌] Mee eeeeeeeeeeee eeeeeeeeeeeeee eeeeeeee eeeeeee ee ee M-eeeee ee eee eeeee eeeeeeee eee eeee eeee eeeeeeee.[‌88‌] Meee eeeee- eee eeeeeeeeeeeeee eeeeeeee eeeeeee eeeeee ee e eeeeeeee ee eee MM eeee eeeeee ee 8.888.88 Å.

Meeeeee eeeeeeee ee eeeeeeee eeeee M-eeeee eeeeeeeee eee eeee eeee eeeeeee ee eeeeeeeeee-eeeee eeeeeeeee.[‌88‌‌88‌] Mee eee ee eeeeee eeeeeeeee eeeee M-eeeeee ee eeeeeee eee eeeeeeeeee eeeeee ee eeeeeeeee eeeeeeeee eeeeeeeee ee eeee-eeeeeee. Me eeeeeeee ee eeeeeeeeeeeeee eeeee M-eeeeeeeeeeeeeee-eeeee eeeeeeeee, ee eeeee e eeeee eeeeee eeee eeee eeee-eeeeeeeeee, eeeeeeee eeeee M-eeeee eeeeeeeee eee eeee eeeeeeeee ee eeee eee eee eeee eeeeee. M-eee eeeeeee eeeeeeeeee ee eeeee eee eeeee M-eeeee eeeeee ee eeeeeeeee ee eeeeeeeee(MM), eeeeee(MM), ee eeeeeeeee(MMM) eeee eeee eeeeeeee.[‌88‌,‌88‌,‌88‌]

Mee eeeeee eeeee eeeeee ee eeeeeeee eeeee M-eeeeee ee eeeeeeeeeee ee eee eeeee eeeee ee eeeee eeeeee eeeeeee. Meeeeee eeeeee eee eeeeee eeeeeeee eeeee M-eeeeee eee ee eee eeeeee ee 8.88.8M.[‌88‌,‌88‌] Meeeeeeeeeeeee eeeee M-eeeeee, eeee ee eeeeeeee 8-eeeee, eeee e eeeee eeeeee eeeeee (ee. 8.8M) ee e eeeeeeeeeee ee eeeee eeeeeee ee eeeee ee eeeeeeeee-eeeeeeeeee eeeeeeeeee. Mee eeeeee eeeeeee ee eeeeeee eeeee eeeee [e.e., M=M (8.8M) eee M=M (8.8M)] eee eeeeeeeeeeee eeeee eeee eeeee ee eeeee M-eeeeee. Mee eeeeeeeeee eeeeee eeee eee eeee eeee eeee eee eeeeeeeeee eee eeeeee eee eeeeeeeeeee ee eπeπ eeeeeee eeeeeee. Mee eeeeeeee eeee ee ee eeeee M-eeeee ee eeeeee ee eeeeeeeeeee ee eeee eeee ee eeeeeee eeeeeee, ee eeeeee eeeeee ee eee eeeeee eeeee, eeeeee-eeeeee eeee.

Meeeeeeeee eeeeeeee ee eee eeeeee eeeeeeee-eeeee eeeeeeeee ee eeeee M-eeeeee ee eeeeeee eeee eee eeeeeeeeeee ee eeeeeeeeeeeeee M-eeeee eeee eeeeee eeeeeee ee eeeee eeeeeeeeeee. Meeeeeee ee eeeeeeeee eeeeeeeeeeeeee M-eeeee eeee eeeeee eeeeeee[‌88‌,‌88‌] eeeeee eee eeeeeeeee eeeeee eeeeeeeeeeee eeeee eeeeee 8. Meeeeeeee, eeeeeeee ee eeeee eeeeeeeeeee[‌88‌] eeee eeeeeeeee eeeeeeeeeeeeee M-eeeee eeeeeeee e eeeeee eeeeeee 8 (Meeeee 8).

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

M eeeeee ee MM eeeeeeeeeeeee eeeeeee ee eeeeeeee eeeee M-eeeeee eeee eeee eeeeeee eee.[‌88‌‌88‌] Mee MM eeee eeeeeeee e eeeeeeeeee eeee eeeeeeeeee ee 888888ee8 ee eee MM eeeeeeee eee e eeeeeeeeeee eeeeeeeeee ee 888ee8 ee eee eee MM. Meee MM eee eee MM eeeeeeeeeeee eeee eeee eeee ee eeeeeeeeeee eeee, ee eeeeeeee, eeeeeeee eeeee M-eeeeee eeeeeeee eeeeeeee eeee ee eeeeee eeeee- ee eeeeeeeeeeeeee eeeeeeee eeee eeeeee, eeee ee eeeeeeee, eeeeee, eee eeeee.[‌88‌,‌88‌] Mee eeeeeeee ee eee eeeeeeee eeee ee eeeeeeee eeeeeee ee eee eMe ee eee eeeeee eeeeee.

Meeeee eeeeeee eeeeeeee eeeee M-eeeeee eee eeeeeeeee eeeeee ee eeee eeeeeeeeeee, eeeeeeee eee eeeeeeee ee e eeeeeeeeeee ee eeeeeee eeeeeeeeeee eee eeeee e [8,8]-Meeeeeeeeeee eeeeeeeeeeeee ee eeeee. Me eeeee eeeee eee eeeeeeeee ee eee eeeee M-eeeee ee eeeeeeeee eee eeeeeee eeeeeeee.

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

Meeeee 8 Meeeeeeeeeeee ee Meeeeeeee 8-Meeeee

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

Meeeee 8 Meeeeeeee ee 8,8,8-Meeeeeeeeeeeeeeeeee[‌88‌]

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

Meeeee 8 Meeeeeee Meeeeeeee 8-Meeeee ee Meeeeeeeeeeee ee eee Meeeeee Meee Meeeeeeeeee ee Meeeeee Meeeeeeeeeeeee[‌88‌,‌88‌]

Meee eeeeeeeee 8-eeeeee, eeee eeeeeeeee 8-eeeeee eee eeeeeeee eeeeeeeee eeee eeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeee eeee eee eeeeeeeee eeeeeeeee. Mee eeeeeeee ee eeeeee eeeeeeeee 8-eeeeee eeee eeee eeeeeeee.[‌88‌] Meee ee eee eeeeeeeee 8-eeeeee eeee eeee eeee eeeeeeee eeeeeee eeeeeee eeeeeeee eee Meee eeeeeeeeeee ee Meeeeeeeeeee eeeeeeeeeeeee ee eeee eeeeeeeeeee, ee eeee e eeeeeee ee eeeeeeee.[‌88‌‌88‌] Me eeeeeee ee eeeee ee Meeeee 8.[‌88‌]

Meeeee 8 Meeeeeeeeeeee ee ee Meeeeeeee 8-Meeee[‌88‌]

Mee M-eeeeee ee eeee-eeeeeeee, eee-eeeeeeee, eee eeeeee eeee eeeeeeee eeeeee eee eeeeeeeee eeeeee ee eeee eeeeeeeeeee (ee eee eeeeeee ee ee eeeeeee ee eeeeeeeeeee eeeeeeeeeee, eeeee eeeee eeeee e Meeeeeeeeeee eeeeeeeeeeeee; eee Meeeeee

Mee eeeee eeeeee eeeeeeeeee eeeeeeeeeeeeee eeeeeeeeee ee eee MM eeee ee 8-eeeeeeeeeeeeeeee 8-eeeee eee 8-eeeeeeeeeeeeeeee M-eeeee eee eeee eeeeeeeee ee ee 88:88 (Meeeee 8).[‌88‌,‌88‌,‌88‌]

Meeeee 8 Meeeeeeeeeeeee Meeeeeeeee ee Mee-Meeeeeee Meeeee M-Meeeee[‌88‌,‌88‌,‌88‌]

Meeeeee eeee eeee eeeeeeeeeeee α ee eeeeeeee ee 8-eeeeeeeeeeeeeeeee eee eeeeeeeeeeee eeeee eee eeeee ee eeeeeeee M-eeeeee eeeeeeee eeeeee eeeeeeee eeeeeeee eeeeeeeee (Meeeee 8).[‌88‌] Mee eeeeeee, eeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeee (8) eeee eeeeeeee eeeeeeee, eee eeeeeee eeeee ee eeeee/eeeeeeeeee M-eeeee ee 88:88. Meeeeee, eee eeeeeeeeee M-eeeee ee eee eeeee eeeeeee eeeeee eeeeee eee eeeeeeeee ee eee-8-eeeee-8,8-eeeeeeeeeeeeeeeeee (8). Meeeeee, eeeeeeeeee eee eeeeee eeee ee eee eeeeeee eeeeeeee ee eeeeeeee eeeeee eeeeeeeeee eeeeee eeeeee M-eeeee eeeeeeeee.

Meeeee 8 Meeeeeeee ee Meeeeeee Meeeee: Meeeeeeeeee Meeeeee eeee Meeeeee Meeeeeee Meeee[‌88‌]

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

Meeeee 8 Meeeeeeeee ee Meeeee Meeee M-Meeeee[‌88‌]

Mee eee ee eeeeee MMMM ee eeeeeee eeeeeee eeeeeeee eeeee M-eeeeee ee eeeeeeee.[‌88‌] Meeee eeeeeee eee eee eeeeeeeee ee eeeeee eeeee M-eeeeee eee eeeeeeeee ee Meeeeeee,, eee

Mee eeeeeeeeeeee eeeeee ee eeeee M-eeeeee eee ee eeeeeeeeee ee MMM eeeeeeeeeeee, eeee e eeeeee eeeee eeeeeee ee eeeeeeee. (M)-8,8,8-Meeeeeeee-8-(8-eeeeeeee)eeeeeee eee (M)-(+)-8,8,8-eeeeeeeee-8-eeeeeeeeeeeee eeee eeee eeee ee eeeeeeeee eeee eee eeeeeeeeeeee eeeeee eee eee eeeeeeee eeeeeeeeeeeee ee eeeeeee(eeee)eeeee M-eeeeee.[‌88‌] Mee eeeeee eeeee eeeeeeee (+)- eee ()-(8,8,8,8-eeeeeeeeeeeeeeeeeee-8,8-eeee)eee(eeeeeeeeeeeeeeee) eeee eeee eeee ee eeeeeee eee eeeeeeeeeeee eeeeee ee eeeee(eeeeee)8-eeeeeeeeee M-eeeee.[‌88‌] Mee eeeeeeee ee (M)-8,8-ee-8-eeeeeeee [(M)-MMMMM] ee e eeeeee eeeeeeeee eeeee eeeeeee eee eee ee 8M-MMM eeeeeeeeeeee ee eeeeeeeeee eeeeeeeee eee eeeeeeeeeeee eeeeee ee eeeee M-eeeeee.[‌88‌]

Mee eeeeeeeee ee eeeeeeee eeeee M-eeeeee ee eeeeeeeee ee MeeeeeMeee, Mee. 88/8, e 88, eee Mee. 88/8e, e 888, ee eeee ee ee eeeee eeeeeee.[‌8‌,‌88‌,‌88‌] Meeeeeee eeeee M-eeeeee eee eeeeeeeeee ee e eeeeee ee eeeeeeeee eeeeeeeee, eeeeeeeee eee Meee eeeeeeeeeee,[‌88‌‌88‌] eee ­Meeeeeeeeeee eeeeeeeeeeeee,[‌88‌‌88‌] eee eee Meeeeeeeee eeeeeeee.[‌88‌,‌88‌] Meee eeee eeee eeeee eee ee eeeeeee ee eeeeeeeeee eeeeeeeee,[‌88‌] ee eee eeeeeeeeee ee eeeeeee eeee eeeeeeeee,[‌88‌‌88‌] eee ee eeeeeeee ee e eeeeee ee eeeee-eeeeeeee eeeeeeeee. Meeee eeeeeee eee eeeeee-eeeeeeee eee eeeeeeeeeeeee ee eeeeeee,[‌88‌‌88‌] eee eeeeeeeee-eeeeeeee eeeeeeeee ee eeeeeeee ee eeeeeeeee {eee Meeeeee ee Meeeeeeee, Mee. 88 [Meeeeeeee (Meeeeee]}[‌88‌‌88‌] eee eeeeeeeee ee eeeeeeeeeeee,[‌88‌] eeee-eeeeeeee eeeeeeeeee,[‌88‌] eee eee MeeeeeMeeee eeeeeeee.[‌88‌‌88‌] Meeee M-eeeeee eeee eeee eeee ee eeeeee eeeeeeeeee[‌88‌] eee ee eeeeeee eee eeeeeeeeee.[‌88‌]

Meeeeeeeeeee, eeeeeeee eeeee M-eeeeee eee eeeeee eeee ee eeeeeeeeee eeeeeeeeeee.[‌88‌‌888‌] Meee eee eeee eeeee ee eeeeeeee eeeeeeee eee eeee eeee eeee ee eeeeeeee eee eeeeeeeee.[‌888‌]