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Please login to access the full content or check if you have access via Variation 4: By Reaction of an Ylide Generated from a Metal Carbenoid and a Sulfide

DOI: 10.1055/sos-SD-037-00188

Aggarwal, V. K.; Crimmin, M.; Riches, S.Science of Synthesis, (200837348.

Sulfonium methylides may be generated by the direct addition of a metal carbenoid to a sulfide.[‌145‌] A novel variation of the SimmonsSmith reaction has been developed in which the carbenoid formed by the reaction of diethylzinc with chloroiodomethane is intercepted by a sulfide to produce the corresponding sulfonium methylide {see also Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section]}.[‌146‌] This can then be used for the in situ epoxidation of carbonyl compounds under nonbasic conditions. Thus, treatment of a series of aliphatic and aromatic aldehydes with diethylzinc, chloroiodomethane, and a dialkyl sulfide results in the synthesis of the corresponding monosubstituted epoxides in high yield (Scheme 46).[‌146‌]

Meeeee 88 Meeeeeee Meeeeeeeeee eeee Meeeeeeee Meeeeeeeee Meeeeeeee ee Meeeeeee ee e Meeeeeeee ee e Meeeeee[‌888‌]

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

Meeeee 88 Meeeeeee Meeeeeeeeee eeee e Meeeeeeee Meeeeeeee Meeeeeeee ee Meeeeeee ee e Meeeeeeee ee e Meeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeeee eeeeee eee eee eeeeeeeeeee ee α-eeeeee eeeeeeeee ee eeeee ee ee eeeeeeeeeee eee eeeee eeeeeeeeee ee eeeeeee eeeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeee. Meeeeeeeee-eeeee eeeeeeeee ee eeeee eeee eeee ee eeeeeeee eeeeeeeeee eee ee eee eeeeee eeeeeeee eeee eeeeeeeee eeeeeeeeeeeee. Meeeeee eee eeeeeeeee eee ee eee eeeeee MeeeeeeMeeee eeeeeeeeeeeeeeee eeeee eeeee eeeeeeeeee.

Meeeeeeeee eeeeeeeee eeee eeeeeeee eeeeeeeee eeeee eeeee eeeeeeeeee eeee eeee eeeeeeee eeeee e eeeeee ee eeeeee eeeeeeee. Meeeeee, ee eee eeeee, eeee eeeeeeee eeeeeeeeeeeeeeeeeeee (8888% ee) eeee eeee eeeeeeee {eee eeee Meeeeee ee Meeeeeeee, Mee. 88 [Meeeeeeeee Meeeeeeee ee Meeeeeeee eee Meeeeee (Meeeeee]}.[‌88‌,‌888‌]

Meeeeeeee eeeeee eeeeeee eeeee eeeeeeeeeee eeeeee ee eee eeeeee eeeeee eee ee eeeeeee eeeeeeee ee eee eeeeeeee ee e eeeeeeeeee-eeeee eeeeeeeee eeeeeee eeee eee eeeeeeeeeeeee eeeee eeeeeeee eeee eee eeeeeeeeeee eeeeeee {eee eeee Meeeeee ee Meeeeeeee, Mee. 88 [Meeeeeeeee Meeeeeeee ee Meeeeeeee eee Meeeeee (Meeeeeee eee]}. Me eeee eeeeee eeeee eeeeeeeee eeeeeeeeee eeeeeeee eeeeeeeeeee eeeeeeeeee, eee eeeeeeee ee eeeeeee ee eee eeee eeeeeee eeeeeeeeee eeee, eee eeee eeeeeeeee eeeeeee eeee eeeeeeeeee ee eeee eeeeee. Mee eeeeeeee eeeeee eee eee eeeee-eeeeeeeee eeeeeeeeeeeee ee eee eeeee eeeeeeee ee eee eeeeeeeeeeeee eeeee eeeeeeeee eeee eeeeeeeee ee eeeeeeeeee (Meeeee 88). Meee eeeeeeeee eeee eeeeeeeee e eeeeeeeeeeee eeeeee ee eee eeeeeee ee eeeeeeee eee eeeeeeeee eeeee eeee eeeeeeeeeee ee eee eeeee eeeeeeee. Mee eeeeeeeee eeeee eeee eeeeee eeee eee eeeeeeee eeeeeee ee eee eeeeeeee eeeeee. Meee eeeeee ee eeeeeeeee eeeeeeeeee ee eeeeeeeeeeee eee eeee ee eeeee ee eeeeeeee, eee eeee ee ee eeeeeeee eee eeee eee eeee eee eeeee eeeeeeee eee eeeeeeeee eeeeeeeee ee eee eeeeeeee.[‌888‌] Meeeeeeeeee ee eeeeee eeeeeeee eeeeeee ee e eeeee, eeeeeeeee, eeeeeeeeee eeeeeee eee eeeeeeee eeeeeeeeeee, eee eeeeeee eeeeeeee eeeeeee eeee eeee eeeeeeeee ee eeee eeee.[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee Meeee ee eee Meeeeeeee ee Meeeeeee eeee Meeeeeeeee Meeeeeeee eeee eee Meeeeeee ee e Meeeeee ee e Meeee Meeeeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeee eeeeeeeeeee ee eee eeeeee eeeeeeee ee eeeeeeeeeeeeeeeeee eeee eee eeeeeeee eeeeeeee eee eee eeeee-eeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeeeeeeee ee eeee eeeee-eeeeeeee (Meeeee 88). Me eeeeeeee, eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeeeee eee ee eeeeeeee, eeeeeeee eee eeee ee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee eee eeeeeee ee eeeeee eeee eee eeeeeeee ee eee eeeee eeeeeeeee eeee e eeeeee eeeeeeeeee ee eeeeeeeeeeeeeeeeee, eee eeeeeeee eee eeeeee eeeeeeee ee eee eeeee eeeeeeee ee eee eeeeeeee eeee eee eeeee.[‌888‌] Meee eee ee eeeeeeee ee (8) eee ee e eeeeee eeeeeeeeeeee eeeeeeeeee eeeeeee (eee e eeeee eeeeeeeee, eeeeee eeeeeeee eeeeee eee eeeeee Me8M > MeMMe > eMeMMe > eMe8M); (8) eeeeeeee eee eee eeeeeeee ee eeee eeeeeeeeeeeeee ee eeeeeee; (8) eeeeeee eee eeeeeeeeeeeee ee eee eeeee eeeeeeee ee e eeeeeee ee eeee eeeeeeee (eeeeeeeee eeee 88e); (8) eeeeeeeeee eee Meeee eeeeeee eee eeeeeeeeee eee eeeeee eeeeeeeeeee ee eee eeeee eeeeeeee.

Meeeee 88 Meeeeeeee Meee Mee Meeeeee eeee Meeeeeee Meeeeeeeeee

Mee eeeeee ee eee eeeee eeeeeeee eee ee eeeeeeeee eeeeee ee eee eeeeeeeeee ee eee eeeeeeeeeee eeeeeee eee eeee eeeeeeeee(MM) eeeeeeeeeeee eee eeeeee(MM) eeeeeeeeeeeeeee eeee eeee eeeeeeee ee eee eeeeeeeee eeeee. Mee eeee ee eee eeeeeeeeeeee eeeeeeee ee eee eeeeeee ee eee eeeee eeeeeeeee ee eeeeeeeee eeee eee eeeeee eeeeeeeeeee eeeee eee eeeee eeeeee eee eeeeee(MM) eeeeeeeee eeeee eeee eeeeee eeeeee ee eeeeeeee eeeeeeeeeee eeee eee eeeeeeeee(MM) eeeeeeeee. Meee ee eeeeeeee ee ee eee ee eee ee eeee eeeeeeeee ee eeeeee(MM) eeeeeee ee e eeeeee(M) eeeeeeeee eeeeeee eeee eeeeeeee eeee eeeee eeeeeeeee. Meeee eeeeee(M) eeeeeeeeee eee, ee eeee, eeee eeeeeeeeee eeeeeeee eee eeeeeee eeeeee eeeee ee eeeeeeeeeeee eeeeeeee eeee eeeeeee eeeeeeee eee, ee eeeeeee, eeeeeeee eeee eeeeeeeeee eeeeeeee eeeeeeee.[‌888‌]

M eeeeee ee eeeeeeee-eeee eee eeeeeeee-eeeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeee eee ee eeeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeee eeeee eeeeeeee eeeeeeeeee. α,β-Meeeeeeeeee eeeeeeeee eeeeeee e eeeeeeeeeeee 8,8-eeeeeeee ee eeeee eee eeeeeeeeeeeee eeeee eeeeeeee. Mee eeeeeeee eeeee eee eeee eeeeeeee ee e eeeeeee ee eeeeeee eee ee eeeee eeeeeeee. Me eeeeeeeeee, eeee-eeeeeeeee eeeeeeeee eeee eeeeee ee eeeeeeeeee ee eeeee eeeeeee eeeee eeeeeee eeeee eeeee eeeeeeee eeeeeeeeee ee eeeee eee eeeeeee eeeeeeee ee eeeeeeeeee eeeeee (8888%). Meeeeeeee, eee eeeeeeee ee eeeeee, eee eee eeeeeeeeee, eeeee eeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeee Meeeeeee Meeeeeeeeee eeee Meeeeeeeee Meeeeeeee eeee eee Meeeeeee ee e Meeeeee ee e Meeee Meeeeeeee[‌888‌,‌888‌]

Mee ee eee eeeeeee eeeeeeeeeee ee eeeee eeeeeeeee eee eee eeeeeeeee eeeeeeeee eeeeee, e eeeeeeee eee eeee eeeeeeeee eee eee ee eeee eeeeeeeeee ee eeee eeeeeee ee e MeeeeeeMeeeeee eeeeeeee, eeeee eeeeeeee eee eeee ee eeeeee eee eeeeeeeeee eeeeeeee eeeeeeeeeeee.[‌888‌,‌888‌] Meee, eeeee eeeeeeeee eee ee eeeeeeeee ee eeeeeeee eeeee ee eee eeeeee eeeeeee (8888°M) ee e eeeeeeeeee ee ee eeeeeeee eeeeeeeee eeeeeeeeeeeeee eeee ee eee eeeeeeee ee e eeeee-eeeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee eeeee eee eeeeeee eee eeee eeeeeee ee eeeeeeee eeeee eee eee eeeee-eeeeeeee eeeeeeee ee eeeeeeee ee eee eeeeeee ee eee eeeee eeee eee eeeee ee eee eeeeee eeeee. Me eee eeeee eeeeeeee ee eeee eeeeee eeeeeeeeeee, eeee eeeeee ee eeeee eeeeeeee eeeeeeeee, eeeeeee eeee eee eeeeeeeeee eeeeeeeee eeeeeeeee eeeee, eeeeee e eeeee eee eeee eeeeeee eeeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeee eeeeeeeeeee eeeeeeeee.

Mee eee eeeeeeee ee eeeeeeeeee, eee eeeeeee eeeeeeee eeeeeeeeee eee: eee eee ee eeeeeeeeeeee ee eee eeeeeee, eeeeeeeeeeeeeeeeeeeeee eeeeeeee ee e eeeee-eeeeeeee eeeeeeee (888eee%), eee eeeeeeeeeeeeeeeeeee (88eee%) ee eee eeeeeee. Mee eeeeeeee ee eeeeeeeee ee 8888°M, eee eeee ee eeeeeee eee eeeeeeeeee ee eee eeeeeeeeeeeeee eeee, eee eeee ee eeeeeeee eee eeee ee eee eeeeeeeeeeeee: eee eeee e eeeeeeeeeeeee eeeee ee eeee eeeeeeeee ee eee eeeee eeeeeeee eee eee eeee e eeeeeeeeeeeee eeeee ee eeeeeeeee eeeeeeee eeeee. Meeeeeeee(MM) eeeeeeeeeeee ee e eeee eeeeeeeee eeeeeeee eeee eeeeee(MM) eeeeeeeeeeeeeee eee eee eeeeeeeeeeeee ee eeeeeeeeeeeeeeeeee ee eee eeeee eeeeeeeee. Mee eeee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeeeeee eeee eee eeeeeeeee(MM) eeeeeeee ee eeeeee eeee eee eeeeeeeeee eeee eee eeeeeeeeeeeeee eeee 88. Me e eeeeee, eee eeeeeeeeeeeee ee eee eeeeeeeee eeeee eeeeeeee ee eeeeeeeee, eee eeee eee eeee eeeeeeeee eee eeeee ee eee eeeeeeee eee eeee eeeeeee eeeeeeeeeee eeee eeeeeeeee eeee eeeee ee eeee eeeeeeeeeeeeee ee eee eeeee eeeeeeee (Meeeee 88). Mee eeeee ee eeee eeeeeeeee eeeeeeeeeee eeeeeeeee ee eeeee, eeee ee eeeee ee eee eeeeeeee eee eee eeee ee eeeeeee eeeeeeeeeeee eeeeeee, eee e eeeeee ee eeeeeeeee eee eeeeeeee eeeeeeeee eee eeeeeee eeee eeee eeeeeeeeee eeeeeeeee e eeeeeee ee eeee eeeeeeeeeeeeee eeeee (Meeeee 88).[‌888‌,‌888‌] Meeeee ee eeeeeeee 88 eee eeeee eeee, eee eeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeee ee eeeeee eeeeee eeee eeeeeee. Me eeeeeeee eeee eeeeeeeeeeeeee eeeeeeeee eeeeee, α,β-eeeeeeeeeee eeeeeeeee eeeeeee e eeeeeeeeeeee 8,8-eeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee. Meeeeee eeee eeeeeeee eee eeeeeeeeeeeee ee eee-eeeeeee eeeeeeeee eeeeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeeee eee eeeeeee eee eeeeeeeee ee eee eee-eeeeeee. Meee, eeeeeeeee eeeeeeeee eee eeeeeeee-eeee eeeeeeeeeeeeee eeeeeeee eeee e eeeeeee ee eee- eee eeeee-eeeeeeee eeeeeeeeee e eeeeeeeeeee eeeeee ee eee eee-eeeeee. Meee eeeeeee eee ee eeeeeeee ee eeeeeeeee eeeeeeeeeeeeeee ee eee eeeee ee eee eeeeeee eeeeeee (Meeeeee

Meeeee 88 Meeeeeeee ee Meeeeeee eeee Meeeee Meeeeeeee eeee eee Meeeeeee ee e Meeeeee ee e Meeeeeeeeeeeee eee Me Meee Meeee Meeeeeeee[‌888‌,‌888‌]

Mee eeeeeee-eeeee eeeeeee 88 eee eeeeee eeee eeeeeeeee ee eeeee ee eeeeeeeeee eeee eee eeeee eee eee eeeeeeeeeeeeeeeeee ee eee eeeeeee. Meeee eee eeeeeeeeee eeeeeeeee eeeee, eeeeeee eeeeeeee ee 8eee% eee ee eeeeeeeee eee eeee eeeeeeeeeeeeeeeeeeee (8888%) eee eeeeeeee eee e eeeee eeeee ee eeeeeeeeee eeeeeee eee eeeeeeee eeeee eeeeeeeee ee ee eeeeeeee eeeeeeeeeee (88°M). Meeeeeee eeeeeeeee eeeeeeeee, e eeeeeee eeeeee eeeeeeeeeeee eeee eeeeeeeeeeee, eeeeeeeeeeeeeee, eee 8,8-eeeeeee eee eeeeeee eeeeeeee eee eeee eeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeeeee.[‌888‌,‌888‌,‌888‌] Mee eeeee ee eee eeeeeeee ee, ee eeeeeee, eee ee eeeeeee ee eeee eeeeeeeee eee eee eeeeeee eeeeeeeee eee ee eee eeeeeeeee eeeeee eeeeeeeee ee eee eeeeee eeeeeee 88 eeee ee eeee eeeeeee eee eeeeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeee eeeeeeeee. Meeeeeee eeeeeeee eee eeeeeeeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeee ee eeee eeeee, eeeeeeeee eeeeeeeee eeee eeeeeeee eeeeee eee eeeeeeeeee eeeeeeee eeeeeeee eeeeee eeee eee eeeeee ee eeeeeeeeeee. Me eeeeeeeeee, eeeeeeeeeeeee eeeeee ee eeeeeeeeee eeeee eeeee eeeeeeeeee eee eee eeeeeeeeeee ee eeeeeee ee eee ee ee eeeeeeee. Meeeeeee-eeeeeeeeee eeeeeeeeee eee eeeeeeee ee eeeeeee e eeeeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeeeee eeeeeeee eeeee eee eeeeee ee eeeeeeeeee eeeee eeeee eeeeeeeeee. Meeeeeeee, eee eeeeeeeee eeeeeeeeee, eee eeeee ee eeeeeeeeeee eee ee eeeeeeeee ee eeeeeeeeee eee eeeeeee eeeeeee (Meeeee 88). Meeeeee 88 ee eeeeee eeeee eeeee eeeeeeee eeeeeeeeee eee eee ee eeeeeeeee ee eeeeee eeeeeeeeeeeeee ee eee eee ee eee eeeeeeee.

Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeee Meeeeeeeeee eee Me Meee Meeee Meeeeeee Meeeeeeeee[‌888‌]

Mee eeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeee eeee eeeeeeeeeeee eee eeee eeeeeeee eee, ee ee eeeeeeee eeeeeeeeee, eee eeeeeeee ee eeeeeeeeee eeeee eeeeeeeeeeeeeeeeee, eeeeeeeeee eeee eeeeeeeee eeeeeeeeee eee-eeeeeee eeeeeeeee.[‌888‌,‌888‌]

Mee eeeeeeeeee ee eeee eeeeeeeeee eeeeee, eeee ee M,M-eeeeeeeeeeeeeeeeeeeeee, eee eeee ee eeeeeeee eeeee eeee eeeeeeeee eeeeeeee ee eeee eeeeeeee eeee eee eeeeeeee eeeee eeeeeeeee. Meeeeeee eeeee eeeeeeeeeee eeeeeeeee, eeee eeeee eeeeeeeee eee eeeeeeeeeeeee eeee eeeeeeeee eeee eee eeee eeeeeeeeeeeee eeeeeeeee eeeee. Mee eeeeeeee ee eeeeeeeee eee eeeeeeee eeeeeeeee eeee M,M-eeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeeee ee eeeeee(MM) eeeeeeeeeeeeeee eee e eeeeeeeeeeee eeeeeee, eeee ee eeeeeeeeeeeeeeeeeee, ee eeeeeeeeeeee ee 88°M (Meeeee 88).[‌888‌] Meeeeeeee eeeeeeee eeeeeeeeeee eee ee eeeeeeee, eeeeeeee eee eeeeeeeeeeeee ee eee eeeee eeeeeeee ee eeeeeeeee, eeeee ee eeeeeeee ee e eeee eeeeeeee ee eee eeeeeeeeeeeeee ee eee eeeeeee eeee e 88 eeee eeeeee. M eeeee ee eeeeeeee eee eeeeeeeee eeeeeeeee eeee eeee eeeeee eeee eeee eeeee eeeeeeeeeee. Mee eeeeeeeeeee ee eeeeeee eeeee eeeee eeeeeeeeee eee eee eeee eeeeeeee. Meeeeeee ee eeeeee eeee eeeeeee eeeeeeeeee eeee eee eeee eeeeeee eeeeeee.[‌888‌]

Meeeee 88 Meeeeeee Meeeeeeeeee eeee Meeee-Meeeeeeeee Meeeeeeee Meeeee Meeeeeeee ee eee Meeeeeee ee e Meeeeeeee eeee e Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: 8-Meeeeeeeeeeee (eeeeeee eeeee) ee e eeeeeeee eeeee eeeeeeeeee, e eeee eee eee eeeeeeee, eee eee eeeee eeee eeeeeeeeeeeee.

MeMM8M (8.88e, 8eeee) eee eeeee ee e eeeeeee eeee ee eeeeeeeeeeeeeeeeeee (8eeee) ee MM8Me8 (8eM) ee ee eeeee eeeee. Meeee 88eee, MeMMM (8eeee) eee eeeee, eeeeeeee ee 8M Me8Me (8eeee) ee eeeeeee. Meeee 88e, eee eeeeeee eee eeeeeee eeee M8M (88eM), eeeeeeeee eeee MM8Me8 (8×88eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee eee eeeee eeeeeee 88, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe eeeeeeee).

eeeee-Meeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeeeeeeee eeeeee eeee 88 (88eeee), MMMMM (8eeee), Me8(MMe)8 (8.8eeee), eee eeeeeee (8eeee), eee eeeeeeee eeeeeeee (88eeee), eee eeeee MeMM eeee eeeee eeeeeeeeeeee ee e 88-eM, eeeee-eeeeeeee eeeee eeeeee eeee e M8 eeeeeee. Mee eeeeeee eee eeeeeee eeeeeeeeee ee ee eee 88eee eeee ee 88°M eee 88e. Meeeeeeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeee ee eeeeeeee ee eee. ee MM8Me (88eM) eee MeMMe (88eM). Mee eeeeeee eeeee eee eeeeee eeee MeMMe eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee ee eeeeee eee eeee eeeee-eeeeeee ee e eeeee eeeee.