Science of Synthesis

Carreño, M. C.; Ribagorda, M., Science of Synthesis, (2006) 28, 649.

Electrochemical oxidation methods are mainly applied to the synthesis of quinone imines. Although these derivatives are detected by cyclic voltammetry and ultraviolet spectroscopy, their instability prevents the isolation of free imine derivatives synthesized by anodic oxidation, except when bulky tert-butyl substituents are surrounding the imine group. A study of the electrochemical oxidation of 2-aminophenols shows that the benzo-1,2-quinone monoimine ‌107‌ is obtained from 2-amino-3,5-di-tert-butylphenol (‌106‌) when the electrooxidation is performed in aprotic solvents (‌Scheme 26‌).[‌65‌] Thus, upon electrolysis of ‌106‌ in acetonitrile in basic medium, at −0.30 V versus the saturated calomel electrode (SCE), using tetraethylammonium perchlorate as electrolyte, ‌107‌ is formed in 40% yield. When dimethyl sulfoxide is used as solvent, a mixture of ‌107‌ and 3,5-di-tert-butylbenzo-1,2-quinone results, under neutral conditions.

‌Meeeee 88‌ Meeeeeeee ee e eeee-Meeee-Meeeeeeeeee Meeee-8,8-eeeeeee Meeeeeeee ee Meeeeeeeeeeeeeee[‌88‌]

Mee eeeeee eeeeeeeee ee M-eeee-8,8,8-eeeeeeeeeeeeeeeeeeeeeee ‌888‌ eeeeee eeeeeeeeeee ee eee 8-eeeeeeeeeeeee eeee, eeeeeee ee M-eeeeeeeeeee eeeee-8,8-eeeeeee eeeeeeeeee ‌888‌.[‌88‌,‌88‌,‌88‌] Mee eeeeeeeeeeee ee ‌888‌ ee eeeeeeeee ee e eeeeeeee/eeeee eeeeeee, eeeee eeeeee eeeeeeeeeee ee eeeeeeeeeee eee e eeeeee eeeeee eeeee eee e eeeeeeee eeeeeee ee ee eeeeeeeee eeee ee e eeeeeeee eeeeeee. Mee eeeeeeeee eeeeeee eeeeee eee eeeeee eeeeee ee ee eeeeeeee ee eeeeee eee eeeeee eeeeeeeeeeeeee, eee eee eeeeeeeeeee eeee 8-eeee-8-(eeeeeeeeeeeeeee)eeeeeeeeeeeeee ‌888‌ ee eeeeeeeee eeee eee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeee ee e-Meeeeee Meeeeeeeee ee Meeeeeeeeeeeeeee ee M-Meee-8,8,8-eeeeeeeeeeeeeeeeeeeeeee ee Meeeeee Meeeeeeeeeee[‌88‌,‌88‌]

Meee eee eeeeeeeeeeee ee ‌888‌ ee eeeeeeeee ee eee eeeeeeeeeeee, eeeeeeee ee eee e-eeeeeee eeeeeeeee ‌888‌ eee eeeeeeeeeeeeee ‌888‌ eee ‌888‌ eee eeeeee, eee eeee eee eeeee eee eeeee eeeeeeee eeee e 8- ee 8-eeeeeee eeeeeeeeeee eeeeeeee eeee ee eeeeeee ee eee eeeeeeee eeeeeeeee ‌888‌ (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeeeee ee M-Meee-8,8,8-eeeeeeeeeeeeeeeeeeeeeeee ee Mee Meeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e M = Me.

e Meeeeee ee eee eeeeee eeeee: M8 = 8-MeMM8M8.

Mee 8-eeeeeeeeeeeeeee eeeeeeeee ee 8,8,8-eeeeeeeeeeee-8-eeeeeee ‌888‌, eeeeee eeeeeeeee ee eee eeeee eeeeeeeeeeeeeeeeeeeeeee, eee ee eeee ee eeeeeeee eeeeeeeeeeeeeeeee ee eeeee-8,8-eeeeeee eeeeeeeeee ‌888‌ (‌Meeeee 88‌).[‌88‌] Me eeee eeee, eee eeeeeeeeeeee ee eeeeeeeee ee eeeeeeeeeeee eee e eeeee eeeeee, eeee ee eeeeeeeee eeeeeee eeeeee eeeeeeee eeeeeeeee, eeeeee eeeeeeeee, ee eeeeee eeeeeeee, ee eeeeeeee ee eeeeeee eeee eeeeee. Mee eeeee eeeeee eee eeeeeeeee ee eee eeeeeeee eeeeeee; eee eeeeeeeeeee eeee eeeeeee eee eeeeeee. Mee eeee eeeeee eee eeeeeeee ee e eee eeeeeeee eeeeeee eee eeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeee-8,8-eeeeeee Meeeeeeeee ee Meeeeeeeeeeeeeee ee 8-Meeeeeeeeee 8,8,8-Meeeeeeee-8-[(8-eeeeeeeeeeeee)eeeee]eee-8-eeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e M eeeeee eeeeee eeeee eee e eeeeeeee eeee eeeeeee eee eeee.

Meeeeeee eeeeeeee, eee eeeeeeee eeee eeee eeeee eeeeeeeee eee eeee ee eeeeeeeeeee eeeeeeeee. Meeee-8,8-eeeeeee eeeeeeeee eeeeeeeeeee, eeee ee eeeeeee eeeeeeeee eeeeeee eeee eeeeeeeee eeeeeeeeeeee ee eee eeeee eeeee, eee ee eeeeeeee eee eeeeee, ee eeeee eee eeeeeee eeee eeeee eeeeeeee ee −88°M. Meee eee ee eeeee eeeeeeeeeee eeee eee eeeeee eeeeeeee eeeeeeeeeeee eeeeeeeeee eee e eeee eeeeeeeeee eeeeeeeee. M eeeeeee eeeee ee eeeeeee eee M-eeee-eeeeeeeeeee eeeeeee ‌888‌ ee eee eeeeee eeeeeeeee ee eeeeee ee eeeeeeeeeeeeeee ‌888‌.[‌88‌,‌88‌] Mee eeeeeeeeeeeeeeee ee eeeeeee, eeeeee, eeeeeeeeeeeeeee, eee eeee-eeeeeeeeeeeeee eeeeeeeeeee ee ‌888‌, ee e eeeeee eeee ee e eeeeeeee eeeeeee ee 8–8% eeeeeeeeee eeeeeee eeeeeeeeeee, eeeeeee eeeeeeeeee eeeeee eeeeee eeeeeee eeeeee eeeeeeee eeeeeeeee ee 8,8-eeeeeeee, ee e eeeeeeeeee eeeeee ee eeeeeeeeee eeeee-8,8-eeeeeee eeeeeeeee eeeeeee ‌888‌. Mee eeeee ee eeeeeeee eeeeeee eeeee eeeeeee ee eeeeeeeee eeee eee eeeee eeeeeeee, eee eeeeeee eeeeeee, eee eeeee eeeeeee ee eee eeeeeeee, eee eeeeee eeeeeeeeee. M eeeeeeeeeee eeeeeeee eeeee eeeee eee e eeeeeeee eeeee eeeeeee eeee eee eeee eeeeeee eeee eeeeee eeeeeeee eeeeeeeee ee 8,8-eeeeeeee eee eee eeeee ee eeeeee.[‌88‌,‌88‌] Mee eeeeeeeee eeeeeee eeeee eeeeeee eee eeee eeeeee ee ee eeee ee eeeeeeeeee eeeeeeeeeeeeeee; eeeeeeeeeeee, eeee eee ee eeeeeee eeeeeeee ee eeeeee eee eeeeeeeeeeeeee. Meee eeeeee eeeeeeee eeeeeeeee ee eeee ee e eeee, eeeeee ee eee eeeeeeee eeee ee eeee eeeeeeeee eee eeeeeee ee eeeee eeeeeeeeeee ee ‌888‌, eeeee eeeeee eeeeeee ee eeeeeee eeee ee eeeeee eee eeeeeeee eeeee eeeeeeeeeee. Meee 8,8-eeeeeeee ee eee eeee eeeeeee ee eee eeeeeeee eeeeee, eee eeeeee ee eee eeeeeeee ‌888‌ eee eeeeeeeee eeeeee. Meee eeeeeeeee ee eeee eeeeeee ee eeeeeee eeeeee eeeeeeeee eeeeeeeeeeee (M8 eee M8) ee M8 eee/ee M8 ee eee eeeeeee eeee. Meee eeeeeeee ee eeee ee eee eeeeeeeeeeee eeeeeee ee 8,8-eeeeeeee, eee eeeeeeee eeeeeee eee ee eeeeeeeeeee ee e eeeeee eeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee M-Meeeeeee Meeee-8,8-eeeeeee Meeeeeeee Meeeeee ee Meeeee Meeeeeeee ee 8-Meeeeeeeeeeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 88‌

e M eeeeee eeeeee eeeee eee e eeeeeeee eeee eeeeeee eee eeee.

Me eee eeeeeee ee eeee, eee eeeeeeeeeeee ee ‌888‌ (M8 = Me; M8 = M8 = M) eee ‌888‌ (M8 = Me; M8 = M8 = M) ee eeeeeeee eeeee eeeeeee eeeeeeeeee eeeee eee eeeeee eeeeeeeee eeeeeee eeeeee ‌888‌ (M8 = Me; M8 = M8 = M) eee ‌888‌ (M8 = Me; M8 = M8 = M), eeeee eee eeeeeeee eeeeeeeee eeeeeeeeeeee eeeeee eee eeeeeeeeeeeeeeeee (‌Meeeee 88‌). Meeeeeee ‌888‌ (M8 = Me; M8 = M8 = M) eee eeee ee eeeeeeeeeee eeee eee M-eeeeeeeeeeee-8,8-eeeeeee eeeeeeeee eeeeee ‌888‌ (M8 = Me; M8 = M8 = M) ee eeeeeeee eeee eeeeee eeeeeee.

‌Meeeee 88‌ Meeeeeeee ee Meeeee Meeeeeeee M-Meeeeeee Meeee-8,8-eeeeeee Meeeeeeeee ee Meeeee Meeeeeeee ee 8-Meeeeeeeeeeeeee[‌88‌]

Mee eeeeeeee ee eee eeeeeee ee 8-eeeeeeeeeeeeee eeeeeeeeeee, eeeee M-eeeeeeeee 8-eeeee- ee 8-eeeeeeeeeeeeee ‌888‌ eeee M-eeeeeeeee 8,8-eeeeee eeeee eeeeeeeeee ‌888‌ ee eeeeee eeeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌,‌88‌] Meeeeeeeee, eeeeeeeeee, eee eeeeee eeeeeeeeee eeee eeee eeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeee eee eee eeeeeee ee eeeee eeeeeeeee. Meeee eeeeee eeeeeeeeeeeee eeeeeeeee eee eeee eeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee, eee eeeeeeeeeeeee ee eee eeeeeeeee, eee eee eeeeeeeeeee. Meeeeee eeeeee eee eeeeeeee ee eeeee eeeeeeeeeeee eeee e eeeeeeee eeeee eeeeeeeeeeeee ee 8 × 88−8 M eeeee e eeeeeeee eeeeeee ee 8.88 M. Meeeeeeeee eee eeee eeeeeeeee ee eeeeeeeeee eee eee eeeeee ee eee eeeee M-eeeeee-8,8-eeeeee eeeee eeeeeeeeee eee eeeee. Meeee eeeee eeeeeeeeee eee eeeeeeee eeeeeeeeee ‌888‌ eee eee eeeeee eeeeeeee ‌888‌ eee eeeeeeeeee eeeeeeeeeeee ee ‌888‌ eee ‌888‌. Me eeeeeee, ee eee eeeeeee ee eeeeeeee, eeee, ee eeeeee, eee eeeeee eeeee eeeeeeeeee eeeeee ee eeeeeeeeeeee eeeeee, eee ee eeeeeeee eeee eeee e eeeee eeeee eeee, eeeeeeee eee ee eeeeee ee eeee ee eeeee.

‌Meeeee 88‌ Meeeeeeee ee M-Meee-8,8-eeeeee Meeee Meeeeeeeee ee Meeeee Meeeeeeee ee 8-Meeee- ee 8-Meeeeeeeeeee[‌88‌,‌88‌,‌88‌]

Meeee-8,8-eeeeeee eeeeeeeee eeeeeeee eeeeeee eee eeee eeeeeeeee eeee 8-eeeeeeeeeee eeeeeeeeeeeeee. Meee, eeeeee eeeeeeeee ee M-(eeeeeeeeeeee)- ee M-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeeee ‌888‌ eeeee eeee ee eee M-eeeeeeeeeeeee-8,8-eeeeeee eeeeeeeee eeeeeeee eeeeeee ‌888‌ eeee eee eeeeeee eeee eee eee eeeeeeeeeeee ee eeeeeeee (‌Meeeee 88‌). Meee eeeeeeeeeeeeeeeeee eeeeeeeeeee[‌88‌] eee eeeeeee eeeeeeeeeee[‌88‌] eee ee eeee ee eeeeeeeeeeee. Meee eee eeeeee ee eeee, eeeeeeee eeee ee eeeee ee eee eeeeeeee eeeeee ee eeeee eeeeeeeeeeeee ee ‌888‌ eee e eeeeee eeee eee ee eeee ee eee eeeeeee eeeeeee ee eeeeeeee.[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee M-(Meeeeeeeeeee)- ee M-(Meeeeeeeeeeee)eeeee-8,8-eeeeeee Meeeeeeee Meeeeee eee Meeeeeeeeeeee ee Meeeee Meeeeeeee ee Meeeeeeeeeeeee[‌88‌,‌88‌]

Meee eee eeeeeeeeeeeeee eeee ee eeeeee eeeeeeeeeee ee eee 8-eeeeeeee eeeeeee e eeeeeeeeeeee eeeeeeee eeeee eeeeeee ee eeeeeee e eeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee, eee eeeeeeeeeeeeeeee eeeeee ee eeeeee eeeeeeeee. Meee, eee eeeeeeee eeeeeeee eeeeeee ee ‌888‌ eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeee eeeeeee ‌888‌ ee eeeeeeeeeeee eeeee eeeeeeeeeeee ee eeeeeee, eeeeeeee eeee eeee eeeeeeee eeeeee (88–88%) (‌Meeeee 88‌).[‌88‌] Meeeee eeeeee eee eeeeeeee eeee eee eeeeeeeeeeee eee ee e eeeeeeeeee eeee. Mee eeeeeeee ee eeeeeeeeeee ‌888‌ eeeee eeeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee eeeee ee eee eeeeeeeeeeeee ‌888‌ ee 88–88% eeeeee. Mee eeeeee ‌888‌ eee ‌888‌, eeeeee e eeeeeeeeee eeee ee M8 ee eee eeeeeeee eeee, eeee eee eeeeeeee ‌888‌ eee ‌888‌, eeeeeeeeeeee, ee eeeeeeeeeeeeeeee. Mee M-(8-eeeeeeeeeeeee)-8,8-eeeeee eeeeeeeee eeeeeee ‌888‌ ee eeeeeeeeeee ee eeeeeeee eeee eeeeee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeeee eeee ‌888‌. Mee eeeeeeeee ee ‌888‌, ‌888‌, eee ‌888‌ eeeeee eeeeeeeeeee ee eee eeee eeeeeeee-eeee eeeeeeee eeee ee eeee eee eeeee eeeeeeeeeee ‌888‌, ‌888‌, eee ‌888‌ ee 88–88% eeeeee. Meeeeeeee, eeeeee eee eeee eeee eeeee eeeeeeeeeeeee ee eee eeeeee eeeeeee eeeeeeeee eeeeeee ee eeeeeee eee ee eee eeeeeeeeeee eeeeeeeeee.

Meeeeeee eeee eeeeee, M-eeeeeeeee-8,8-eeeeeee eeeee eeeeeeeeeeeee ‌888‌ eee eeeeeeeeeeee ‌888‌ eee eeeeeeeee eeee 8-(eeeeeeeee)eeeeeeeeeeeee eeeee ‌888‌ ee eee eeeeeeeeeeeee eeeeeeee ‌888‌, eeeeee eeeeeeee ee eeeeeeeee eeee eeeeee. Mee eeeeeeeeeeee ee eeee eeeee ee eeeeeee eee ee eeeeeeeee eee eee eeeeeeeeeeeeee. Mee eeeeeee ‌888‌ eee eeee eeeeee eeee eee eeeeeeeeeeeee eeeeeeee ‌888‌ (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeee ee M-Meeeeeeee-8,8-eeeeeee Meeeeeeee Meeeeeeeeeee eee Meeeeeeeeeeee ee Meeeee Meeeeeeee ee M-Meee 8-Meeeeeeeeee Meeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Me-eeee-eeeee-8-eeeeeeeeeeeeee-8,8-eeeeeee (‌888‌):[‌88‌]

M eeee ee ‌888‌ (88 eeee) ee MeMM (88 eM) eeeeeeeeee 8.8 M Me8M+MeM8− eee Me8M+MM− (88 eeee) eee eeeeeeeee ee eeeeeeeeeeee ee −8.88 M ee MMM ee e eee-eeeeeeeeeee eeee eeeeeee ee e 88-ee eeee, eeeeee-eeeeeee, eeeeeeeeee Meeee eeee, eeeeee eeee eeeeeeeeee eeeeeeeeeee eeee (Me8M+MeM8−). Mee eeeeeee eeeeeeeee eeeeeeeeeee eeeeeeeee e Meeeeee Me eeeee eeeeeee eeeeeeeee (eeee 8.88 ee8) eee e Me/MeMe, eeeeeee-eeeee eeee, eeeeeeeee eeeeeeeee (eeeeee eeee ee Me8M+Me− eeee eee eeeeeeee ee 8.888 M ee MMM) ee e Meeeee eeeeeeeee. Mee eeeeeeeee eeeeeeeeeee eeeeeeeee e Me eeee eeeeeeeee. Mee eee eeee eee eeeeeee eee ee e eeeeeee eeeeeeee eeeee eee (eee M8 eeeeeeeeee). Mee eeeeeeeee eeeeee eeee eee eeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee ee ee ee eeeee e eeeeee eeeee, eeeee eee eeeeeeeee ee eeeeee (eee Me8M+MeM8− eeeeeeee eeeeeeeeeee). Mee eeeeee eeee eee eeeeeeee eee eee eeeeeeee eee eeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeee eeeeeee eeee eeee eeeeeee. Mee eeeeeeeee eeeee eeeee (‌888‌) eee eeeeeee ee eeeeeeeeee eee eee eeeeee eeeeeeee eeeeeeeeee ee eeeee ‌888‌ ee e eeeeee eeeee; eeeee: 88%.

Meeee-8,8-eeeeeee Meeeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeee eeeeeeeeeeee eee eeeeeeee eeeeeeee eee eeeeeee eeee eeeeeeeeeee eeeeeeeee eeeeee ee eeeeeee.

Mee 8,8,8-eeeeeeeee-8-[(8-eeeeeeeeeeeee)eeeee]eee-8-eeeeee ‌888‌ (8.8 eeee), eeeeeeeee ee e eeeeeee ee MeMM (8 eM) eee eee. ee MeMMM8 (8 eM) eeeeeeeeee MeMeM8 (8.8 eeee), eee eeeeeeeeeeee ee −88°M ee ee eeeeeeeee eeee eeeee e eeeeee M eeeee eee e Me-eeee eeeeeee ee e eeeeeeee eeeeeee ee 8 eM·ee−8 eee 8.8 M·eee−8 ee eeeeeeeeeee. Meeee eeeeeeeeeee ee eeee ee eee MeMM eeeee eeeeeee eeeeeeee, eee eeeeeee eeeee eee eeeeeeeee (MeMMe). Mee eeeeeeee eeee eeeeee eeee eeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee) ee eeee eee eeeeeee; eeeee: 88–88%.

M-(8,8-Meeeeeeeeeeeeeeeee-8,8-eeee-8-eeeeeee)eeeeeeeee (‌888‌, M8 = Me; M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeee eeeeeeeeeeee eee eeeeeeee eeeeeeee eee eeeeeee eeee eeeeeeeeeee eeeeeeeee eeeeee ee eeeeeee.

M eeee ee eee eeeeeee ‌888‌ (M8 = Me; M8 = M8 = M; 888.8 ee, 8.88 eeee), MeMeM8 (8.8 e, 88.8 eeee), eee 8,8-eeeeeeee (8.8 eM, 8.88 eeee) ee MeMM (888 eM) eee eeeeeeeeee eeeeeeee ee ee eeeeeeeee eeee eeeee e Me eeeeee eeeee (8.8 ee × 8 ee) eee e Me eeee eeeeeee (8 ee) ee e eeeeeeee eeeeeee (8.8 M) eee 88 eee. Mee MeMM eee eeeeeee eee eee eeeeeee eee eeeeeeee eeee M8M (888 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM); eee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee (88 eM) eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eeeee eee. Mee 8,8-eeeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee (<8.8 Meee) eeeeeeeee ee eeee eee eeeeeee; eeeee: 888 ee (88%).

M-(8,8-Meeeeeeeeeeeeeeeee-8,8-eeee-8-eeeeeee)-8-eeeeeeeeeeeeeeeeee (‌888‌, M8 = 8-Mee); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeee eeeeeeeeeeee eee eeeeeeee eeeeeeee eee eeeeeee eeee eeeeeeeeeee eeeeeeeee eeeeee ee eeeeeee.

Meeeeeeeeeee eee eeeeeee eee ee e eeeeee-eeee eeeeeeeee ee eeeeeee eeeee MeMM, eeeee e eeeeeeee 88-eeee Me eeeee eeeee (8 ee × 8 ee eeeeeeee) eee e Me eeee eeeeeee (8.8 ee × 88 ee). M eeee ee ‌888‌ (M8 = 8-Mee; 888 ee, 8.88 eeee), eeeeeeee (888 μM, 8.88 eeee), eee MeMeM8 (888 ee, 8.8 eeee) ee MeMM (888 eM) eee eeeeeeeeee eeeeeeee ee 8°M, eeeee eeeeeeee eeeeeee (8.8 M, 8 M). Mee eeeeeeee eee eeeeeeeee ee MMM. Meeee 8 e, eee MeMM eeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee, eeeeeeeee (MeMMe), eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee eeee ee e eeeeee eeeee eeeee eeeeeeeeeeeeeeeee (Me8M); eeeee: 888 ee (88%); ee 888.8–888.8°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.