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Please login to access the full content or check if you have access via Variation 1: 1,3-Elimination of Two Heteroatoms

DOI: 10.1055/sos-SD-048-00305

de Meijere, A.; Kozhushkov, S. I.Science of Synthesis, (200948489.

Beginning with the first preparation of cyclopropane itself by treatment of 1,3-dibromopropane with sodium,[‌8‌] the reductive ring closure of 1,3-dihaloalkanes has become a generally applicable method for the synthesis of cyclopropanes 35, especially for the preparation of nonfunctionally substituted ones (Scheme 14).[‌57‌] Thus, as unsubstituted cyclopropane was and remains an efficient anesthetic,[‌58‌] its industrial production from 1,3-dichloropropane by treatment with zinc or magnesium has been patented several times.[‌59‌,‌60‌] According to the Beilstein Crossfire Data File, ca. 1000 cyclizations of this type have been realized for X=Y=halide, while reactions for X=Y=OR1 or SR1 are less common; for a summary of these results, see HoubenWeyl, Vol.4/3, p32 and Vol.E 17a, p29. This reductive ring closure can be achieved by the action of metals (Zn, Mg, Na, Li) or organometallic species (MeLi, etc.), but most cleanly proceeds electrochemically. However, in the chemistry of cyclopropane-containing hydrocarbons, this type of cyclization has mostly been applied to the synthesis of spiro-fused and 1,2-ring-annulated cyclopropanes as well as of cage molecules. Thus, the preparation of spiropentane 37 (n=1; Z=H) from 1,3-dibromo-2,2-bis(bromomethyl)propane or from 1,1-bis(bromomethyl)cyclopropane (36, n=1; Z=H) by the so-called Gustavson reaction[‌61‌] was dramatically improved by using zinc dust in the presence of the di- or tetrasodium salt of ethylenediaminetetraacetic acid to trap the zinc(II) bromide formed and thus prevent catalyzed ring expansion and ring-opening reactions.[‌62‌] Applying these conditions, a whole series of spiro[2.n+1]alkanes 37 with and without deuterium labels[‌63‌,‌64‌] can be prepared in moderate to good yields, and dispiro[]octane (39) is obtained from diiodide 38 in 76% yield using a very similar protocol.[‌65‌] 1,3-Elimination from bis(arylmethyl)-substituted 1,3-dihalopropanes to give substituted 1,1-dibenzylcyclopropanes 40 can be performed by treatment with samarium(II) iodide;[‌66‌] however, zinc in ethanol appears to be more efficient and less expensive in this cyclization giving dibenzylcyclopropanes quantitatively.[‌67‌] Very good results in such ring closures of 1,3-dihaloalkanes have been achieved using an electrochemical cathodic reduction.[‌68‌]

Meeeee 88 Meeeeeeeeee ee Meeee[8.e+8]eeeeeee eee Meeeeee[]eeeeee ee Meeeeeeee Meee Meeeeee ee Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

e M Meeee (%) Mee
8 M 88 [‌88‌]
8 M 88 [‌88‌]
8 M 88 [‌88‌]
8 M 88 [‌88‌]
8 M 88 [‌88‌]
8 M 88 [‌88‌]
8 M 88 [‌88‌]
8 M 88 [‌88‌]

Meee eeee ee eeeeeeeeeee eee eeee ee eeeeeee ee eee eeeeeeeee ee 8,8-eeeee eeeeeeeeeeee eeeeeeeeee. Mee eeeeeeee eee, eeeeeee[8.8.8]eeeeee (88), eee ee eeeeeeee ee eeeeeeeee eeee eeeeeee ee 8,8-eeeeeeeee ee eee eeeee, e.e. eeeeee eeee eeeeeeeee ee eee eeeeee eeeeeeeeeeee eeee eeee 88 (Meeeee 88) ee eeee eeeeeeeeeeee eeeeeeeee ee eeee eeeee ee eeeeeee ee eee eeeeeee MM eeee ee 88. Meeeeeeeeee eeeeeeee, e.e. 88 ee 88, eee ee eeeeeeeee eeeeeeee eeee eee 8,8-eeeeeeeee 88 ee 88, eeeeeeeeeeee (Meeeeee 88 eee 88). Meeeeeee eeeeeeeeeee eee eeee eeeeeeee eee eeeeeeeeee eee eeee eee eeee, eee eeeee eeeee[‌88‌,‌88‌] eeeeeee eeeeeeee eee eeeeeeee ee eeeee eeeeee eee eeee e eeeeee eeeeee ee eeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeee eee eeeeeeeeeee eeeeeeeeeeee.[‌88‌‌88‌] Meeeeeeeeeee, eee eeee eeeeee eeeeeeee ee eeee eeee eee eeeeeeee ee eeeeeeeee eee eeeeeeeeeeeeeee eeeeee.[‌88‌]

Meeeee 88 Meeeeee[8.8.8]eeeeee: Mee Meeee ee Meeeeeeeeee ee Meeeeeeee Meee Meeeeee ee 8,8-Meeeeeeee eee eee Meeeeeeee ee 8,8-Meeeeeeeeee Meeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M8 Meeee Meeeeee Meee (°M) Meeee (%) Mee
M M Me eeeeeee 888 88e [‌88‌]
M M Me MMM 88 88 [‌88‌]
M Me Me MMM 88 88 [‌88‌]
Me M Me MMM 88 88 [‌88‌]

e 8-[88M]Meeeeee[8.8.8]eeeeee eee eeeeeeee eeeeeeee.

Meeeee 88 Meeeeeeee ee Meeeeee[8.8.8]eeeeeee eeee Meeeeeeee ee eee Meeeeee Meee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 M8 M M Meeeeeeeee Meeee (%) Mee
M M Me Me Me, eeeeeee, 888°M, 8e 8888e [‌88‌]
M M Me Me eeeeeeeeeeee, MMM, Me8MMe 88e [‌88‌]
M Me Me Me Me, eeeeeee, 888°M, 8.8e 88 [‌88‌]
Me Me Me Me Me, eeeeeee, 888°M, 8.8e 88 [‌88‌]
Me Me Me Me Me/Me, MMM, 88°M, 8e 88 [‌88‌]
Me Me Me Me eeeeeeeeeeee, MMM, MeMe 8888e [‌88‌]
Me Me Me Me Me/Me, MMM, 88°M, 88e 88 [‌88‌]

e Mee eeeeeee ee eeeeeeeeeeee eeee e eeeeeee ee eeeeee.

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

Meeeee 88 Meeeeeeee ee Meeeeeee[,8]eeeeee eeee Meeeeeeee ee eee Meeeeee Meee[‌88‌]

Meee eeeeee ee eeeeee eeeeeeeee eeee eeeeeee ee 8,8-eeeeeeeee ee eeeeeeeeeeee eeeeee eee eee eeeeeeeeeee ee eeeeeeee[,8]eeeeeee (88, [8.8.8]eeeeeeeeee) eee eeeee [e.8.8]eeeeeeeeeee eeee 88 ee 88 (Meeeee 88).[‌88‌‌88‌] Mee [8.8.8]eeeeeeeeee (88) eee eeeeeeeee eeee eeeeeee ee eeeeeeee eeeeeee eeeee ee eeeeeeeee eeee eeeeeeeeeeeee ee eeeee eeeeeeeeeeee eeeeeeee. Me ee eee eeeeeeee eeee, eee eeeeee eeee eeee eeeeeeee; eeeeeee, ee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeee, eee eeeee eeee eeeeeeeeeeeee 88 eeeeeee ee ee eeeeeeeeeeeee eeee eeeeeeee, ee eee eeeeeeee eeeeeeeee eee eeeeee ee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeee eeeeeeeeeee eeeeeee. Meeeeeeeee 88 ee eeeeeeeeee ee ee ee 88% eeeee ee eeeee e; eee eeeeee ee 8-eeeeeeeeeee eee 8,8-eeeeeeeeeeeee eeeeeeeeeee 88 eee eeeee.

Meeeee 88 Meeeeeeee ee [8.8.8]Meeeeeeeee eee Meeeeeeeeee Meeeeeeeeee ee Meeeee ee Meeeee Meeeeeeee Meee Meeeeee ee 8,8-Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 M8 Meee (°M) Meee (e) Meeee (%) Mee
M M 88 ee 88 8.8 88 [‌88‌]
M M 88 ee 8 8.8 8888 [‌88‌]
Me M 88 ee 88 88 88 [‌88‌]
(MM8)8Me M 88 ee 88 8.8 88 [‌88‌]
Me Me 88 ee 88 88 88 [‌88‌]
(MM8)8 88 ee 88 88 88 [‌88‌]

8,8-Meeeeee[‌88‌] eee 8,8-eeeeeeeeeeeee 8,8-eeeeeee[‌88‌] [8.8.8]eeeeeeeeeee eee eeee ee eeeeeeee ee eeee eeeeee ee eeeeeeee ee eeee eeeeee (8888 eee 8888%, eeeeeeeeeeee). [8.8.8]Meeeeeeeee (88) eee eeeeeeee ee 8888 eeee 8,8-eeeeeeeeeeeeee[8.8.8]eeeeeee 88 (M=Me) eee eee eeeee eeee (Meeeee 88).[‌88‌] Meeeeee, eeee eeeeeeee eee eeee eeeeeeeeeee eeee eeeeeeeee eeeeeeeeeeee, ee eee eeeeeeee eeeeeeee 88 ee eee eeeeeee eeeeeeeee. Meeeeeeeeeee, ee ee eee eeee ee eeeeeee[8.8.8]eeeeee, eee eeeeeeee 88 (M=M), eeeee ee eeeeee eeeeeeee eeee eeeeeeee 88, eee ee eeee eee eee eeeeeeeee ee eeeeeee-eeee 88 eee ee e eeee-eeee eeeeeee eeee ee [8.8.8]eeeeeeeeee (88).[‌88‌]

Meeeee 88 Meeeeeeee ee [8.8.8]Meeeeeeeee ee Meeeeeeee Meee Meeeeee ee 8,8-Meeeeeeee[‌88‌,‌88‌]

Mee eeeeee [e.8.8]eeeeeeeeeee 88 eee eeee ee eeeeeeee ee e eeeeeeeee eeee eeeeeee ee eeeeeeeeeee 8,8-eeeeeeeee 88 ee 88 ee eee eeeee (Meeeee 88). Meeeeee, ee eeeee eeeeeeeeeeee 88 eee eeee eeeeeeeee eeeeee eeee [8.8.8]eeeeeeeeeee 88 ee 88 eee eeee eeeee ee eeeeeee eeeeeeeeeeeeee, eeee eee eeeeeeee ee eeee eeeee (eee eee eeee eeeeeeeeeeee) eeeeee.[‌88‌‌88‌] Mee eeeeeeeee eeeeeeeeee eee [e.8.8]eeeeeeeeeee 88 eeee eeeeeeeee 88 eee eeeeeee eee eeee ee eeeee eee [8.8.8]eeeeeeeeeee 88 eee 88.

Meeeee 88 Meeeeeeee ee Meeeee [e.8.8]Meeeeeeeeee ee Meeeeeeee Meee Meeeeee ee 8,8-Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

Meeeeeeee e M Meeeeeeeee Meeeee (%) Mee
88 8 MeMe, Me8M, 88 ee 88°M, 88e e.e. [‌88‌]
88 8 MeMe, Me8M, 88 ee 88°M, 88e 8888 [‌88‌]
88 8 MeMe, Me8M, 88 ee 88°M, 88e 88 [‌88‌]
88 8 M M (eeeee), 888°M, 8Meee e.e. [‌88‌]
88 8 Me Me, eeeeeeee, 888°M 88 [‌88‌]

e e.e.=eee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

8,8,8,8-Meeeeeeeeeeeeeeee[8.e+8]eeeeeee (88, e=88; M=M); Meeeeee Meeeeeeee:[‌88‌]

Mee 8,8-eee(eeeeeeeeeee-e8)eeeeeeeeeee (88, e=88; M=M; 8.88eee) eee eeeee eeeeeeee ee e eeeeeee eeeeeee ee eeee eeeeeeeeeee eeee (88.8eeee), MeMM (888.8eeee), MeM (8.8eeee), M8M (88eM), MeMM (88eM), eee Me eeee (888.8eeee) ee 88°M eeee e eeeeee ee 8e. Mee eeeeeeeee eeeeeee eee eeeeeee ee eee eeee eeeeeeeeeee eee ee eeeeeeeeee 8e; eee eeeeeeeeeee eee eeee eeeeeeeee eee eeeee eeeeeeee eeeeeee eeeeeeee eeee e eeee eeee (88°M). Mee eeeeeeeee eeeeeee eeee eeeeeeeeeee eeee e eeeeeeeeee eeee eeeeee, eee eee eeeeeeeeeeee eeee eeeeeeee ee eeeeeeeee eeeeeee ee 88°M (e=8); eeeee: 88% (88.8% eeeeee); ee 88.8°M (e=8); eeeee: 88% (88.8% eeeeee); ee 88°M (e=8); eeeee: 88% (88% eeeeee); eee ee 888°M (e=8); eeeee: 88% (88.8% eeeeee).

Meeeeee[8.8.8.e]eeeeee (88):[‌88‌]

Me e eeeeeee eeeeeeeee eeeeeee ee eee eeeeeeee eeee ee eeee8M8M (88.88e, 8.888eee) eee MeMM (88.88e, 8.888eee) ee M8M (88eM) eee MeMM (888eM) eeee eeeee MeM (8.88e, 88.8eeee) eee Me eeee (88.88e, 8.888eee), eeee ee eee eeeeeee. Meeeeeee 88 (88.88e, 88.8eeee) eee eeee eeeee eeeeeeee ee eee eeee eeeeeeeeeee eeee e eeeeee ee 8e. Meeee eeeeeeee eee eeeeeee ee eeeeee eee ee eeeeeeeeee 8e, ee eee eeeeee, eeeeee eeee eee-eeee M8M (888eM), eee eeeeeeeee eeee eeeeeee (8×888eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M, eee. ee MM8Me, eee eeeee, eee eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeeeee eeeeeee ee eeeeeeeeeeee eeeee e 88-ee eeeeeeeeeeeee eeeeee, eee eee eeeeeee eee eeeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.88e (88%); ee 888°M/888Meee; 88MMMM (MMMe8, δ): 88.8 (8MM8), 88.8 (8M), 88.8 (8MM8)

8-[88M]Meeeeee[8.8.8]eeeeee (8-[88M]-88, M8=M8=M); Meeeeee Meeeeeeee:[‌88‌]

M 88-eM, eee-eeeeee, eeeee-eeeeeeee eeeee eee eeeeeeee eeee e eeeeeeee eeeeeeee eee eee e eeeeee eeeeeeeee. Mee eeeeeeeee eee eeeeeeeee ee e eeee eeeeeeee ee eee M8. Mee eeee ee eeee eee eeeeeeeee ee e eeeeee eeeeeee. Mee eeeee eee eeeeeee eeee Me (8.88e, 8.888eeee) eee eeeee eeeeeee (88eM). Mee eeeeee eee eeeeee ee eeeeee, eeeee eee eeeeee Me eee eeeeeeeee eeee eee eeeeeeee eee. M eeee ee 8-[88M]-8-eeeee-8-(eeeeeeeeeeee)eeeeeeeeeeee (8-[88M]-88, M8=M8=M; 8.8e, 88eeee) ee eeeeeee (8eM) eee eeeee ee eee eeeeeeeee eeeeeee eeee e 88-eee eeeeee; eeeeee eee eeeeeeeeee eee ee eeeeeeeeee 8e eeeee e eeee eeeeee ee M8 (ee. 8eM·e8). Mee eeeeeeee ee eee eeee eeee (ee. 8eM) eeee eeeeeeeeeee ee ee eeee e eeeee eeeee (eeeeee eeee eee M8) ee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.88e (88%); ee ee. 88°M/888Meee; 8MMMM (MMM-e8, δ): 8.88 (e, 8M), 8.88 (e, 8M, MM,M=88.8Me, MM,M=888.8Me), 8.888.88 (e, 8M); 88MMMM (MMM-e8, δ): 8.8 (MM+88MM, MM,M=888.8Me), 88.8 (8MM8, MM,M=88.8Me). Mee eeeeeee eee ee eeeeee eeeeeeeeeee ee e eeeeee ee e eee eeeeeee eeee ee ee eeeeeee/eee eee eeee ee eee eeeeee eeeeeee ee ee eeeeee, eeeeee eeeee eeeeeee eeeeeeee, ee e eeeeeee.

8-Meeeeeeeeeeee[8.8.8]eeeeee (88, M8=M; M8=Me); Meeeeee Meeeeeeee:[‌88‌]

M 8-M, eeeee-eeeeee eeeee eeeeeeee eeee e eeeee eeee eeeeee eeeee, eeeeeeee eeeeee, eeeeeeee eeeeeeee eee, eee eeeeeee eeeeee eee eeeee ee eeeeeee eeeee e eeeeee ee M8. Mee eeeeee eeee e eeeeeeeeee eeeeeee eee eeeee ee ee eeeeeeeee. Mee eeeeee eeeee eee eeee eeeeeee eeee eeeee eeeeeee (888eM) (eeeeeeeee eeee Me) eee Me eeeee (88.8e, 8.8eee), eeeee eeee M8, eee eeeeee eeeee eee eeeeeee eeeeeeee ee eee eeeeee ee eee eeeee. M eeee ee 8,8-eeeeeeee-8-eeeeeeeeeeeeeeeee (88, M8=M; M8=Me; M=M=Me; 88.8e, 8.888eee) ee eeeeeee (88eM) eee eeeee eeee e eeeeee ee 8.8e; eee eeeeeee eee eeeeee eeeee eeeeee eee ee eeeeeeeeee 8e. Meeeeeeeeeeeee eee eeeeeee eee eeeeeee ee eeeeeeeeeeee, eeeeeeeeee eeeeeeeee eeee ee ee ee 88°M. Mee eeeeeeeeee eee eeeeeeeeeee eeeeeee eee eeee eeeeee eeeeee ee eeee e eeeeeeeee eeeeee; eeeee: 88.8e (88%); ee 88.888.8°M/888Meee; 8MMMM (eeee, δ): 8.88 (e, 8M), 8.8 (e, 8M), 8.88 (e, 8 M), 8.88 (e, 8M).

8,8-Meeeeeeeeeeee[8.8.8]eeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Meeee eeeeeeee eeeeeeee, e eeee ee eeeeeeee[,8]eeeeee (88; 8.88e, 88eeee) ee eeeeee (888eM) eee eeeeee ee 8°M. Meeee M8 (88.88e, 88eeee) eee eeeee eeeeee ee eeeee eeeeeeee eeeee eee eeeeeee eee eeeeeeeeee eeee eeeeeeeeeeee eeeee (888-M eeee). Meeee 88e, eeee eee eeeeee eeeee ee eee eeeeeee ee eeeeee eeeee, eee eeeeeeee eeee eeeeeeeeee, eeeeeee eeeee, eeeee-eeeeeeeee eeeeeeee, eeeee eeee eeeeee eeee eeee eeeeee eee eeeee eeee eeeeeeeee (88 eeeeeee eeeeeeeeee eeee eeeeeeeeee ee M8); eeeee: 88.88e (88%); ee 888888°M; 8MMMM (eeeeeee-e8, δ): 8.88 (e, 8M, MM8), 8.88 (e, 8M, MMM), 8.88 (e, 8M, MM); 88MMMM (eeeeeee-e8, δ): 88.8 (8MMM), 88.8 (8MM8), 88.88 (8MM).

Meeeeee-Meee Meeeeeee[,8]eeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeee ee eeeeee eeeee; eeee eeeeeeeeeee eeeeee ee eeeeeeeee ee e eeee-eeeeeeeeee eeee, eee eeeeeeeee eeeeeeeee eeee ee eeeeeeeeee, eeeeeeeee, eee eeee ee eee eeeeeee eeeeee ee eeeeeee.

M eeee ee eeeeeeee 88 (88.88e, 88eeee) ee MMMM (888eM) eee eeeeeee eeee MMM (8.88e, 888eeee) ee ee eee 8e. Meee, eee eeeee 88 eee eeeeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeeee eeee e eeee eeee (88°M). Meeeeeeeeeeeee eeee e eeeee eeeeee ee MeM8 eeee eeeeeee-eeee 88 ee e eeeeeeeee eeeeee; eeeee: 8.88e (88%); ee 8888°M/888Meee.

Meeeeeee[,8]eeeeeee (88, [8.8.8]Meeeeeeeee) ee Meeeeee Meeee; Meeeeee Meeeeeeee:[‌88‌]

M 8.88M eeee ee MeMe ee Me8M (8eM, 88.88eeee) eee eeeee eeeeeeee ee e eeeeeee eeee ee eeeeeeeeeee 88 (8.88e, 8.88eeee) ee eeeee Me8M (88eM) ee 88°M eeee e eeeeee ee 8.8e. Mee eeeeeee eee eeeeeee ee eeee ee ee eeeee eeeeeeee eeee e eeeeee ee 8e, eeeee eee eeeeeeeee ee e eeeeeeeee eeeeeeeeeee eee eeeeeeee. Mee eeeeeee eee eee eeeeeeee eeeeeeee eeee eeee-ee-eeee eeeeeeeee ee 88Meee eeee e 88°M eeee eeee e eeeeeeeeee Meeeeee eeeee eeee eee eeee ee 88°M, ee eeee 88.88e ee ee Me8M eeee, 8MMMM eeeeeeee ee eeeee eeeeee (eeeeeee Me8M) eeee eee eeeeeee eee MeMe (δ 8.88) eee 88 (δ 8.88). Mee eeeeeeeeeeeee ee 88 eee eeeeeeeeee ee ee 8.88% e/e; eeee eeeeeeeeeee ee e eeeee ee 888ee (88%). Meee eeeeeeeeeee eee eeeeeeeee eeeeeee eeeee eeee eeeeeeeeee ee 88 eeeeeee eeee 8.88 ee 88.8e (eeeeeeeeee eeeeeee) eee eeeeeeeeeeeeee ee ee eeeee eeeee ee eeee ee eee eee eeeeeeeee eeeee, eeeeeeeee eeeeeeeeeee eee eeee eeeeee ee 88 ee eee eeeeeeeeeee.

Meeeeee-Meee Meeeeeee[,8]eeeeeee (88, [8.8.8]Meeeeeeeee); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeee ee eeeeee eeeee; eee eeeeeeeeeee eeeeee ee eeeeeeeee ee e eeee-eeeeeeeeee eeee, eee eeeeeeeee eeeeeeeee eeee ee eeeeeeeeee, eeeeeeeee, eee eeee ee eee eeeeeee eeeeee ee eeeeeee.

Me e eeee ee 88 (8.88e, 888eeee) ee Me8M (888eM), eeeeeeee ee eeeeeeeee eeeee eeee 88 (88.8e, 888eeee) eee e 8.88M eeee ee MeMe ee Me8M (888eM, 888eeee), eee eeeee eeeeeeee e eeee ee M8 (88.8e, 888eeee) ee e eeeeeee/Me8M eeeeeee (8:8; 8.8M) ee 88°M. Meeeee eeee eeeeeeee eee eeeeeeee eeeee eee eeeeeeeeee eeee e 888-M eeeeeeeeeeee eeee. Meeee eeeeeee ee ee, eee eeee eee eeeeee eeee 88% ee Me8M8M8 eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee; eee eeeeeeeee eeeee 88 (M=M) eee eeeeeeee ee eeeeeee eeee eeee eeeeeee (888eM) ee eeeeee 88 (M=M) ee e eeeeeeee eeeeee eeeee; eeeee: 88.8e (88%); 8MMMM (MMMe8, δ): 8.88 (e, 8M).

Meeee M8, eeeeeeee 88 (M=M; 88.8e, 88.8eeee) eee eeeee ee eeeeeee eeeeeeee ee e eeeeeee eeeeeee ee MeMM (8.88e, 888eeee) eee eeeee MMMM (888eM); eee eeeeeee eee eeee eeeeeee eee ee eeeeeeeeee 88eee. Mee eeeee eee eeeeeeeee ee e eeeeeee eeee (88°M) eeeeeeee ee e Meeeeee eeeee, eeeee eee eeeeee eeee eee M8 eee eeeeeee eeee eeeeeeeeeeee (8.8ee). Meeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeeeee ee ee eee ee ee. 8.8Meee eee 88eee, eeeeeeeee 88 ee e eeeeeeeee eeeeee; eeeee: 8.88e (88%); 8MMMM (eeeeeee-e8, δ): 8.88 (e, 8M); 88MMMM (eeeeeee-e8, δ): 8.8 (8M), 88.8 (8MM8).

8-Meeee[8.8.8]eeeeeeeeeee 88 [M8=(MM8)8Me eee Meeeee; M8=M]; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeeeeeeeee 88 (88eeee) ee eeeee Me8M (888eM) eee eeeee, eeeeeeee, e 8.8M eeee ee MeMe ee Me8M (888eeee) ee 88°M. Mee eeeeeee eee eeee eeeeee ee ee eee eeeeeee eee ee eeeeeeeeee 88eee. Meeeeeee M8M (888eM) eee eeeee eeeeee, eee eeeeeeeee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeee (MeMM8). Meee ee eee Me8M eee eeeeeee ee eeeeeeeeeeee ee eeeeeee eeeeeeee (8Meee) ee 88°M; eee eeeeeeeee eeeeee (eeeeeeeee ee 8MMMM) eeee eeeeeee eeeee eeeee eeeeeeee (8.888Meee) ee 88°M. Mee eeeeeee eee eeeeeeee ee eee-eeeeeeeeeee eeeeeeeeeeeeeeeee (88°M) eeee eee-eeeeeee eeeeeeeee eeeee eeeee M8; eeeee: 8888%; eeeeee eee eeeeeeeee 8888%.