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Please login to access the full content or check if you have access via Variation 3: Curtius Rearrangement

DOI: 10.1055/sos-SD-040-00241

Purchase, R.; Sainsbury, M.Science of Synthesis, (200940404.

Both the Lossen and Schmidt (Section rearrangements utilize the same key step as that of the Curtius rearrangement in which an acyl azide 206 undergoes thermolytic (or photolytic) loss of nitrogen and an isocyanate 207 is produced {see also Science of Synthesis, Vol. 18 [Four CarbonHeteroatom Bonds: XCX, X=C=X, X2C=X, CX4 (Section]}.[‌243‌‌250‌] As in the two other related rearrangements the isocyanate may then be hydrolyzed to afford an amine (Scheme 65).

Meeeee 88 Meeeeee Meeeeeeeeeeee ee Meee Meeeee

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

Meeeee 88 Meeeeeeee ee eeeee-Meeeeeeeeeee-8,8-eeeeeee Meeeeeeeeeeeeee[‌888‌]

Mee eee eeeeeeeee ee eeeeeee-8,8,8-eeeeeeeeeee eeeeeeee (888) eee eeeeeee eeeeeeee ee eee eeeeeeeee eeee 8,8,8-eeeeeeeeeeeeeeeeee eeeeeeeeeee (888) eee eeeeee eeeee eee eeeeeee eeee eee eeeeeee eeee ee 8,8-eeeeeeeeeeeeee. Me eeee eeee eee eeee eeeee ee eee eeeeeeee eee ee ee eeeeeeeeee eeee 8,8,8-eeeeeeeeeeeeeeeeeeee (888) ee eeeeeeeeee eeeeeee eee eeeeeeee ee 8,8-eeeeeeeeeeeeee ee eeeeee. Me eee eeeee eeee eee eeeeeeeeee ee eeeeeeeeee eeee eeeeeee-8,8,8-eeeeeeee eeeeeeeeeeeeeeee (888) ee eeeeeeeee eeee eeeeeeeeeeee eeeeeeeeeeee eeee; eee eeeeeee eeeee ee 88% (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeee-8,8,8-eeeeeeee Meeeeeeeeeeeeeee[‌888‌]

Meee eeeeee eeeee-8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee (888) eee eeeee eeeeeeeeeeeee eee eeeeeee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeeeee ee eeeeee, eeeee ee eeeeeee eeee eeeeee eeeee eeeeeee eee eeeeeeee eeeee 888. Meee eeeeeee ee eee eeeeeeee, eee eee ee eeeeeeeeeee eeeeeeeeee ee eeeeeee ee ee eeeeeee ee 88°M eee 8eeeee. Mee eeeeeeeeeeeee eeeeeeeeee ee eeee eeeeeeeee ee eeee eeee eee eeee-eeeee eeeeeeeee 888, eee eeee eeeeeeee ee eeeeeeee eee eeeeeeeeee ee e eeeeeeee eeee ee eeeeee (8M,8M)-()-eeeee-8-eeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (888, Meeeeeeeeeeeeee eeeeeeeeeeeee) ee 88% eeeeeee eeeee. Mee eeee eeee, Meeeeeeeeeeeeee, ee e eeee eeeeeeee eeee eee eee eeeeeeeee ee eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee (8M,8M)-()-eeeee-8-Meeeeeeeeeeeeeeeeeeeee Meeeeeeeeeeee[‌888‌]

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

Meeeee 88 Meeee-Meeee Meeeeeeee ee Meeeee eee Meeeeeeeee Meeee Meeeeee Meeeeeeeeeeeee[‌888‌]

Meeeeeeeeeeee, e eeeeeee eeee eeeeeee eee eeee eeeeeeee eee eeeeeeeeee Meeeeee eeeeeeeeeeeeee ee e eeeeeeeeee eeeeeee, eeeeeee eeeeeeee eeeeeeeeee ee eeeeeeeeeee eee eeeeeeee eeeeee eeeeeeee eee ee eee eeeee eeeeeee ee eeeeeeeee eee eeeeeeee eeeee eeeeeeeeeee ee eee eee eeee.[‌888‌] Meeeeee eee eeee eeee eeeeeeeeeeeeeeeeee eeeee ee eeeeee eeeee ee ee eeeeee eeee ee eeeeeee eeeeeeeeee eeeee eeee eeeeee; eeee, eee eeeeeee, eee eeee eeeeeeeeee 888 ee eeeeeeee eeee eee eeeeee eeeeeeeeeeeeee eeee 888 ee eeeeeeeee eeee eeee eeeeeee. Mee eeeeeeeeeeeee eeeeeeeeeeeee eeeee eeee ee eee eeeeeeee, eeeeeee, eee eee eeeeeeeeeeee eeeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeee ee eeeeee eee eeeeee-eeeeeeeee eeeeeeee 888. Meee eeee eeeeeeee ee eeeee eee eeeeeeee, eee ee eeeee eeeeeeeeeee ee eeeeee eee eeeeeeee eeee eeeee eeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeee eeeeeee eeeeeeeeee e eeeeeeeee eeeeee ee eeeeeeeee(MM) eeeeeee eee eeeeeeeeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeee, (M)-8-(Meeeeeeeeee)-8-eeeeeeeeeeeeee Meee[‌888‌]

Meeeeee eee eeeeeee ee eeeeeeeeeeeeeeeeee eeeee ee e eeeeeee ee Meeeeee eeeeeeeee ee ee eeeee; eeeeeeee, eeeee eee e eeeeee ee eeeee eeeeeeeeeeeee ee eee eee. Meeee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeee eee eee eeeeeeeeeee eee eeeeeeeeee eeee eeeeeeee eeeeeeeeeeee. Mee eeeeeeee ee ee eee e eeeeeee ee ee-eeee-eeeee eeeeeeeeeee eee eeeeee eeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee ee eeeeeeee eeee-eeeee eeeeeeeeeeee ee eeee. Meee eeeeeeeeeeee eee eeee ee eeeeeeee eeee e eeeeeeeeee eeee 888 ee e eeeeeee ee e Meeeeee-eeee eeeeeeeeeeeee eeee eeeeeeeeee eeeee eee eeee-eeeee eeeeeeeeee 888. Meee(MM) eeeeeeeeeeeeeeeeeeeeeeeee eeee ee e eeeeeeee eee e eeeeee ee eeeeeeee ee eeee eeeeeee eee eeeee ee Meeeee 88, eeeeeeee ee eee eeee ee 8-eeeeeeeeeeeeee eeee [888, M8=MM(Me)Me] eee eeeeeee eeeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeeeee eeee-eeeee eeeee.[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee eeee-Meeee Meeeeeeeee eeee Meeeeeeeee Meeee Meeee eeee-Meeee Meeeeeeeeeee ee eee Meeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) Mee
8-eeeeeeeee 88 [‌888‌,‌888‌]
MM(Me)Me 88 [‌888‌,‌888‌]
MM8eMe 88 [‌888‌,‌888‌]
88 [‌888‌,‌888‌]
(MM8)8MM=MMe8 88 [‌888‌,‌888‌]
(MM8)8Me 88 [‌888‌,‌888‌]
88 [‌888‌,‌888‌]
MM(Me)Me 88e [‌888‌,‌888‌]

e Meeeeee ee eeeeeeeeeee ee eee eeee-eeeee eeeee.

Mee eeee eeeeeeeee eee ee eeee eeee ee eeeeeeeeeeeeeee α-eeeeeeeeeee eeeeeeeeee eeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeee eeeee eeeee eeee eeeeeeeee ee eeeeeeeeeeeee. Mee eeee eeeeeeeeeeee ee eeeeeeee ee Meeeee 88 eeeee eee eeeeee eeee 888 ee eeeeeeeee eeee eee eeeeeeeee eeeee 888 eeeeeee eeee ee eeeeeeeeeeeeee eeeeeeeee. Me eeee eeeeeee eeee-eeeee eeeeeee eee eeee eeeeee ee eeeeeee eee eeeeeeeee, ee eeee eeee ee eeeeee eee eeeeeeee ee eee eeeeeeee eeeeee; eeeeeee, eee eeeeeeeee eee eeeee eee eeeeeeeeee ee eeeee eeeeeeeee eeeee eeeeeeeeeeee ee eeeeee eeeeeeeee ee eee ee eeeeeeeee.[‌888‌] Mee eeee eeeeee ee eeee eeeeee ee eee eeeeeeeeee ee α,α-eeeeeeeeeeeee eeeee 888 eeee eee eeeeeeeeeeeee eeeeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeee Meeeeeeeeeeeee Meeeeee ee α-Meeeeeeeeee Meeeeeeeee[‌88‌,‌888‌]

Meeeeeeeeeeeee, eeee ee eeeee eeeeeeeeeeeee, eee eeee ee eeee ee eeeee ee eeee-eeeee eeeeeeeeeee, eeeeeeee eee eeeeee ee eeeee ee eeeeeeee eeeeeeeee ee eeeee ee eeeeee eeeeee eeeeeeee eeeee eee eee eeeeeeee eeeeeeeee.[‌888‌] M eeeeee ee eeeeeeeeeeee eeeeee eee eeeee eeeeeeeeeee eee eeee eeeeee eeee eee eeeeeeeeeeeee eeeeeeeeee eeeee eeeee eeeeeeeeeeee Meeeeee eeeeeeeeeeeeee; eeeee eeeeeeeeeeee eeeeeee eeeeeeeeee[‌888‌,‌888‌] eee eeeeee, eee eeeee eeeeeeeeeee ee eeeee eee eeeeeeeeee eeeeeeeee ee eeeeeee ee eeee eee eeeee ee eeeeeeeee eee eeeeeeeeeeeeee.[‌888‌] Me eeee eeeee eeeeeee eeeeeeeeeeeeee ee e eeeeeeee eeeee ee eeeeeeeee eeeeee eeeeeeeeeee; eee eeeeeee, eeeee-8-eeeeeeee eeeeee 888 eee eeeeeeee eeee eee eeeeeeeeeeeee eeeee-8-eeeeeeeeee eeee eeeeeeeee ee eeeeeeeee eeee eeeeee eeeee ee eeeee, eee eeeee eeeeeeee eee eeee eeeeee ee e eeeeeee/eeeeeee eeeeeee ee 88°M ee eeeeeeee eee eeeeeeeeeee 888. Meeeee eeee eeeeeeeee eeeee eeeeeeeeeeeee eeee eeeeeeee ee eeee eeeeeeeeee eeee eee ee eeeeeee ee eee eeeeeeee ee Meeeeeee eeeeeeee ee eeee eee eeeeeeeeeee eeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee M-Meeeeeee 8-Meeeeeeeeee[‌888‌]

M eee eeee ee eee eeeeeeeee ee eee eeee-eeeeeeeee eeee Meeeeee MM-8888 (888, eeeeeeeeee eeeeeeeee) eeeeeee Meeeeee eeeeeeeeeee; eeee eee eeeeee eeee 888, eeeeeeeeeeeeeeeeee eeeee, eee eeeeeeeeeeeee eeeee eeeeeeee ee eeeeeee eee eeeeeeeeeeeeeeeeeee-8-eee 888, eeeee ee eeee eeeeee eee eeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeeee eeee Meeeeee (Meeeee 88).[‌888‌] Me eeeeeeeeeee eeeeeeee eeeeeee e MeeeeMeeee eeeeeeee eeeeeee 8-(eeeeeeeeeeeeeee)eeee-8,8-eeeee (888) eee (8M)-eee-8-eeeeeeee eeeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeeeeeeeee eee 8-(eeeeeeeeeeeee)eeeeeeee eeee eeeee ee eee eeeeee eeeeee eeeeeee 888, eeeee eeee eeeeee ee eeeeee ee eeee-eeeee eeeeeee eeeeeeee eee eeeeeeeeeeeeeeeeeee-8-eee 888 eee e eeeeee Meeeeee eeeeeeeeeeeee. Meee eeeeeeee ee eeee eeee eeeeee, eee eeeeeeeeeeee eeeeeeeee eeee eee eeee eeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeee Meeeeeeeeeeeee ee Mee Meeee ee Mee Meeeeeeee ee Meeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

eeeee-8,8-Mee[(eeee-eeeeeeeeeeeeee)eeeee]eeeeeeeeeeee (888):[‌888‌]

MMMMMMM: Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

M eeee ee eee eeeeeeeeee 888 (8.88e, 8.88eeee) ee eeeeeee eee eeeee eeeeeeee ee e eeee ee MeM8 (8.88e, 88 eeee) ee M8M eeee ee 8°M. Meeee 8e ee eeee eeeeeeeeeee, eee eeeeeee eee eeeeeee eeee eee-eeee M8M (88eM) eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (88eM), eeee eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee (MMMMMMM: eee eeee eeee eee ee eeeeeeeeee ee eeeeeeee eeeeeee) ee eeeee e eeeeee eee. Mee eeeeeee (88eM) eee eeeee ee eee eeeeee eee eee eee eeee eeee eeeeee eee eeeeee ee eeeeee eee 8e (MMMMMMM: eeeeeeee eeeeeeeeee eeeee e eeeee eeeeee ee eeeeeeee), eeeeee eee eeeeeee eee eeeeeee ee eeeeee eee eeeeeeeeeeee, eeee e eeeeee eee, eeeee eee eeeeeeee eeee e-MeMM (88eM) eee 88e. Meeeeee ee eeeeee e-MeMM eeee e eeeeeeeee eeeee, eeeee eee eeeeeeeeeeeeee (MeMMe); eeeee: 8.88e (88%).

eeeee-Meeeeeeeeeee-8,8-eeeeeee Meeeeeeeeeeeeee (888):[‌888‌]

M eeee ee eee eeeeeeeeeee 888 (8.88e, 8.88eeee) ee MeMM (88eM) eee eeeeeee eeee 8M MMe (8.8eM) eee eee eeeeeee eee eeeeee ee eeeeee eee 8e. Mee eeeeeeee eeeeeeeeee eeee eeee eeeeeeeeee eee eeeee eeeeeee eeeeeeee ee eeeee eee eeeee eeeeeeee; eeeee: 8.88e (888%).

8,8,8-Meeeeeeeeeeeeeeeeeee (888):[‌888‌]

MMMMMMM: Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

Meeeeee-8,8,8-eeeeeeeeeee eeeeeeeeeee (888; 8.88e, 8.88eee) ee 8,8-eeeeeeeeeeeeee (88eM) eee eeeee eeee e eeeeee ee 88eee ee e eeee ee MeM8 (8.88eee) ee M8M (8eM) eeee eee eeeeee ee ee eee eeee. Meeee eee eeeeeeee, eee eeeee eee eeeeeee eeee eee eee eeee eee eee eeeeeeee eeee eeee ee eeeee ee ee. Meeee 8e, eeeeeee-8,8,8-eeeeeeeeeee eeeeeeee (888) eee eeeeeeeeee eeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeeee e eeeeeeeeeeee eeeeeeeeee eeeeee. Mee eeeeeee eeeee eee eeeeee eeee 8,8-eeeeeeeeeeeeee (8eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeee [MeMM8 (8e)] eee 88eee, eeeeee eeeee eeeeee ee e eeeee eeee eee eeeeeeeee eeeeee e eeeee eeeeee. Mee eeee eee eeee eeeeeeee eee 8.8e, ee eeeee eee eeeeeeee eee eeeeeeee, eee eeee eee eeeeeee eee eeeeeee ee eeeeee eeeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeeeeeeeee (eeeeeeee) ee eeeeeee; eeeee: 8.8e (88%).

Meeeeee-8,8,8-eeeeeeee Meeeeeeeeeeeeeee (888):[‌888‌]

8,8,8-Meeeeeeeeeeeeeeeeeee (888; 8.88ee, 8.88eee) eee eeeee ee eee eeeeeee eeee eeeeeeee ee eeeee MMe (88eM) ee ee. Mee eeee eee eeeeee ee 88°M ee e eeeee eeee eee eeeeeee eeeee ee eeee MM8 eee eeeeeee (ee. 8e). MeMM (88eM) eee eeee eeeeeeeeee, eee eee eeeeeee eee eeeeeeee eeeee e eeeeee-eeeeeee eeeeee. Mee eeeee eeeeeeee eee eeeeeee eeee eee eeee eee eeeee ee e eeeeee eeee (88Meee/88°M) ee eeeeee eee eeeee eeeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.88e (88%).

Meeee (8eM,8M,8M,8M,8eM)-8-Meeeeee-8-eee-8-(eeeeee-8-eeeee)eeeeeeeee-8,8-eeeeeeeeeee-8-eeeeeeeeeee (888):[‌888‌]

Me8M (88e, 888eeee) eee eeee eeeeeeeeeeeeeeeeee eeeee (88e, ee. 8.88eee) (ee eee eeeeeee) eeee eeeee ee eee eeee 888 (88.8e, 8.88eee) ee MM8Me8 (888eM), eee eee eeee eee eeeeee ee ee 88°M eee 88e. Mee eeeeeee eee eeeeeee eeee MM8Me8 (888eM) eee eeeeee ee eeee eeee 8M MMe (888eM), 8% ee MeMMM8 (888eM), eee eeeee (8 × 888eM). Mee eee eeeeeee eeeeee eeee eeee eeeeeeeee eeee MM8Me8 (888eM) eee eee eeeeeee eeeeee eeee eeeeeeee, eeeee (Me8MM8), eee eeeeeeeeee ee eeeee e eeeeeeeee eeeeeee (88.8e). Meee eeeeeeee eee eeeeeeeeeee ee eee MeMMe (888eM) eee eeeeeee ee eeeeeeeeeeeee ee eeeeeeee eee eeee ee 88°M eee 88e. Mee eeeee eeee eeeeee eee eeeeeeeee eee eeeeee eeee eeee MeMMe, eee eeee eeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8e (88%).