Science of Synthesis

Balaban, T. S.; Balaban, A. T., Science of Synthesis, (2003) 14, 82.

This variation, the dehydrocyclization of α,β-unsaturated ketones with methyl(ene) ketones and related compounds (‌Table 2‌), is the method of choice for the preparation of many polyarylpyrylium salts, such as the formation of ‌117‌. The reaction of 1,3-diphenylprop-2-en-1-one and acetophenone in the presence of iron(III) chloride/acetic anhydride yielding 2,4,6-triphenylpyrylium tetrachloroferrate was discovered by Dilthey in 1919.[‌213‌] Although the oxidation process involved in this dehydrocyclization was ascribed to a valency change from iron(III) to iron(II), it seems more likely that the hydride acceptor is the acetyl cation (the resulting acetaldehyde then undergoes condensations leading to products that are washed away). 1,3-Diphenylpropan-1-one is usually isolated as the hydride addition product of 1,3-diphenylprop-2-en-1-one and therefore the use of 2 equivalents of 1,3-diphenylprop-2-en-1-one for each equivalent of acetophenone is necessary,[‌214‌] as was used in the preparation of 2,4,6-triphenylpyrylium tetrafluoroborate (‌51‌, X = BF4; ‌Scheme 92‌).[‌215‌]

‌Meeee 8‌ Meeeeeeee ee Meeeeeee Meeee eeee 8,8-Meeeeeeeeeee-8-ee-8-eee Meeeeeeeeee eee Meeeee(eee) Meeeeee[‌88‌,‌88‌,‌88‌,‌888‌,‌888‌,‌888‌–‌888‌]

e e.e. = eee eeeeeeee.

e 8,8,8-(M8M)8M8M8M

‌Meeeee 88‌ Meeeeeeee ee 8,8,8-Meeeeeeeeeeeeeeee Meeee[‌888‌–‌888‌,‌888‌]

8-Meeee-8,8,8-eeeeeeeeeeeeeeeee eeeee ‌888‌ eeee eeee eeee eeeeeeee eeee 8,8-eeeeeeeeeeee-8-ee-8-eee ee eeeeeee eeeeeeee eee eeeee eeeeee eeeeee ee eee eeeeeeee ee e Meeee eeee eeee ee eeeee eeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Meeeeeeeeeeee, eeeeeeeeeeeeeeeeee eeeee eee eeee ee eeee ee eeeeeee eee eeeeeeeee,[‌888‌] eeeeeeee eeeeeeeeeeeeeeee eeee ee eeee eeeeee eeee, eeeee eeeeeee ee eeeeeeee eeeeeeee, eeeeee eee eeeeeeee eeeee. Meee eeeeeee eeeeeeeee eee ee eeee ee eeeeeee eeeee, eeeeeeee eee eeeeeeeee ee eeeeeeee eeeee eeee eeee-eeeeeeeee eeeeeeeeeeee eeee ee eeeee eeeee. M eeeeee eeeeeeeeeeee ee eeee eeeeeeee, eeeeeeeee 8,8-eeeeeeeeeeee(8,8-eeeeeeeeeeeeeeee-8-ee) eee(eeeeeeeeeeeeeeeeee) eeee 8 eeeeeeeeeee eeeeeeeeeeee eee 8,8-eee(8-eee-8-eeeeeeeeee-8-eeee)eeeeeee eeee eeee(MMM) eeeeeeee ee eeeeee eeeeeeeee. Me eeee eeee eee eeeeeeee eeeeeee eeeeeeee ee eee eeeeee eeeeee.

‌Meeeee 88‌ Meeeeeeee ee 8-Meeee-8,8,8-eeeeeeeeeeeeeeeee Meeee[‌888‌]

‌Meeeeeeeeee 88‌

e Meeeee M: MM8•MMe8, 888°M, 8 e. Mee eeeeeeeeeeeeeeeee eeeeeee ee eeeee ee eeeeeeeeeee; Meeeee M: MeM, MeMM, eeeeee, 88 eee.

‌Meeeee 88‌ eeeee eeeeeeee ee 8,8,8-eeeeeeeeeeeeeee eeeeeeeeeeeeeeeeee eeee 8,8-eeeeeeeeee-8-ee-8-eee eeeeeeeeeee eee ee eeeeeeeeeeee eeeeeeeeee.[‌888‌]

‌Meeeee 88‌ 8,8,8-Meeeeeeeeeeeeee Meeeeeeeeeeeeeeeee eeee 8,8-Meeeeeeeee-8-ee-8-eeee eee Meeeeeeeeeee Meeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeee eeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeeee ‌888‌ eeee α,β-eeeeeeeeeee eeeeeee eee eeeeeeeee eeeeeee ee eee eeeeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeee ee eeeeeeeeee eeee ee eeeeeee eeee eee eeeee ee ‌Meeeee 88‌.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeeeeee Meeeeeeeeee Meeeeeee Meeee[‌888‌]

‌Meeeeeeeeee 88‌

Me8	Me8	M8	M8	M	Meee (°M)	Meee (e)	Meeee (%)	ee (°M)	Mee
Me	Me	Me	Me	MM8	888	8	88	888	[‌888‌]
Me	Me	Me	Me	MM8	88	8	88	888	[‌888‌]
Me	Me	Me	Me	MM8	888	8	88	888–888	[‌888‌]
Me	Me	Me	Me	MM8	888	8	88	888–888	[‌888‌]
Me	Me	Me	Me	MeM8	888	8	88	888–888	[‌888‌]
Me	Me	(MM8)8		MeM8	8	8	88	888–888	[‌888‌]
e		Me	Me	MM8	888	8	88	888	[‌888‌]
e		Me	Me	MM8	888	8	88	888	[‌888‌]
e		Me	Me	MeM8	888	8	88	888–888	[‌888‌]
e		Me	Me	MM8	888	8	88	888–888	[‌888‌]
e		e	MM8	888	8	88	888	[‌888‌]
Me	Me	e		MM8	888	8	88	888–888	[‌888‌]
e-Me	Me	e		Me	888	8	88	888	[‌888‌]
Me	Me	e		MM8	888	8	88	888	[‌888‌]

e Mee eeeeeeeee eeeee ee eeee ee eee α,β-eeeeeeeeeee eeeeee Me8MMMM=MMMe8.

e Mee eeeeeeeee eeeee ee eeee ee eee eeeeeeeee eeeeee M8MMMM8M8.

M eeeeee eeeeeeeee ee eeeeeeee eeeee ‌888‌–‌888‌ eeee eeeeeeeeeee eeeeeeeeeeee ee 8-, 8-, ee 8-eeeeeeeee eee ee eeeeeeee ee eeeeee eeeeee (‌Meeeeee 88‌–‌88‌).[‌888‌] Me eeeeeeeeeee eeeeee ee ee eeeeeeee eeeeee(eee)-eeeeeeeeeee eeeeeeee eeeee eeee eeeeeeee eeeeeeeee; eeee eee eeeeee eee eeeeeeee eee eeeeee (eee Meeeeee ‌88.8.8.8‌). 8,8-Meeeeeeeeeeee-8,8-eeee-8-eeee eee ee eeeeeeeee eeee eeeeee(eee) eeeeeee eeeeeeee 8,8-eeeeeeee-8-eeeeeeeeeeeeee eeeee ‌888‌, eee e eeeeeeeeee eeeeeeeeeeeeeee eeee eeeeeee eeeeeeeee e 8,8-eeeeeeeeeeeeeeee eeee eeee eee eeeeeeeeeeee eeee eeeee eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeee Meeee eeee Meeeeeeeeee Meeeeeeeeeee ee eee 8-Meeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeee, 8,8-eeeeeeee-8-eeeeeeeeeeeeee eeeeeeeeeeee ‌888‌ eee ee eeeeeeee eeee eeeeee eeeeee(eee) eeeeeee eee 8,8-eeeeeeeeeeeee-8,8-eeee-8-eee eeee eeeeeeeeeeeeeeeeee eeeeeeeeeee ee eeeeeee eeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeee Meeee eeee Meeeeeeeeee Meeeeeeeeeee ee 8- ee 8-Meeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

8,8-Meeeeeee-8-eeeeeeeeeeeeee eeeeeeeeeeeeeeeeee (‌888‌) ee eeee eeeeee eeee 8,8-eeeeeeeeeeee-8-ee-8-eee eee 8-eeeeeeeee-8-ee-8-eee, eeee eeeeee eeee eeeeeeeee eeee(MMM) eeeeeeee ee eeeeee eeeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8,8-Meeeeeee-8-eeeeeeeeeeeeee Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeee eeeee ‌888‌ eeee eeeeeeeeeeeee 8-eeeeeeeee eee eeeeee eeee eeeeeeeee eeeeeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee, eeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeeeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeee eeee eee 88 eee (‌Meeeee 88‌).[‌888‌] Meeeeeeee, eeeeeeeeeeeeee, eeeeeeeeeeee, eee eeeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee 8,8-eeeeeeeeeeeeeeee eeeeeeeeeee (‌888‌) (‌Meeeee 888‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeee Meeee eeee ee Meeeeeeeeeeee 8-Meeeeeee[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8,8-Meeeeeeeeeeeeeee Meeeeeeeeee[‌888‌]

Mee eeeeeeeeeee ee eeeeeee 8-eeee-eeeee-8-eeeeeeeeeeeeee eeeee ‌888‌ (M8 = Me, e-Me) ee eeeee ee ‌Meeeee 888‌,[‌888‌,‌888‌,‌888‌,‌888‌] eee ee ‌Meeeee 888‌ eee eeeeeeeeeee ee 8-eeeee-8-eeeeee-8,8-eeeeeeeeeeeeeeee eeeeeeeeeee (‌888‌) ee eeeeeeeeeee.[‌888‌] 8-(8-Meee-8-eeeee)eeeeeeee eeeee ‌888‌ eee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeeee-eeeeeeeeeee eeeeee eee 8,8-eeeeeeeeeeee-8-ee-8-eee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-eeee-Meeee-8-eeeeeeeeeeeeee Meeee[‌888‌,‌888‌,‌888‌,‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-Meeee-8-eeeeee-8,8-eeeeeeeeeeeeeeee Meeeeeeeeee[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8,8-Meeeeeee-8-(8-eeee-8-eeeee)eeeeeeee Meeee[‌888‌]

‌Meeeeeeeeee 888‌

Mee eee(8,8-eeeeeeeeeeeeeeee) eeee ‌888‌ eeeeeee ee eeeeeeeee eee eeeeeeee eeee eeeeeeeeeeee eee eee eeeeeee ee 8,8-eeeeeeeeeeeeeee eee 8 eeeeeeeeeee ee (eeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee (‌Meeeee 888‌).[‌888‌] Meee ‌888‌ eee eeeeeee eeee eeeeeeeeeee, e eee(8-eeeeeeeeeeeeeeee) eeee eeeeee, eeeee eee eeeee ee eeeeee e eeeeeeeeee eeeeeeeee (ee eeeee ee MMM) ee eeeeeeeee eeee eeeeee eeeeeee ee eeeeeeeeeeee. Mee-eeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeee eeee eeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeee eeee (eee Meeeeee ‌88.8.8.8.8.8‌) eeeeeeee eee eeeeeeeeeee eeeeeeee ee eee 8,8-eeeeeeeeeeee(eeeeeeee) eeee ‌888‌; eeee eee eeeeeeee ee eee eeeeeeeeeeeee (eeeee: 8%; ee >888°M).[‌888‌,‌888‌,‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8,8′-(8,8-Meeeeeeee)eee(8,8-eeeeeeeeeeeeeeee) Mee(eeeeeeeeeeeeeeeee)[‌888‌]

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

‌Meeeee 888‌ Meeeeeeee ee Meeeeeeeeee Meeeeeee Meeee eeee 8,8-Meeeeeeeeeeee Meeee[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee Meeee-Meeeeee Meeeeeeeeee Meeeeeee Meeee eeee 8,8-Meeeeeeeeeeee[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee eee Meeee Meee ee 8,8-Meeeeeee-8-(8-eeeeeeeeeee)eeeeeeee Meeeeeeee[‌888‌]

Meeeeeee eeeee ‌888‌ eeee eee eeeeeeeeeeee eeeeeeeeeeee eeeeeeeeeeee-8-ee ee 8-eeeeeee eee eeeeeeee eeee α,β-eeeeeeeeeee eeeeeee eee eee eeeeeeeeeeeee eeeeee-eeeeeeeeeee eeeeeeeeeeee (‌Meeeee 888‌).[‌888‌,‌888‌]

‌Meeeee 888‌ Meeeeeeee ee Meeeeeee Meeee eeee Meeeeeeeeeee Meeeeeeeeeee[‌888‌,‌888‌]

‌Meeeeeeeeee 888‌

M8	M8	Meeee (%)	ee (°M)	Mee
Me		88	>888	[‌888‌]
e-Me	8-eeeeeee	88	888–888	[‌888‌]
Me	8-eeeeeee	88	888–888	[‌888‌]

8,8-Meeeeeeeeeeeee eeeee ‌888‌ eeeeeeeeeee eeee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(M) ee eee 8-eeeeeeee eee eeeeeeee eeee (eeeeee-η8-eeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee(M) eee ee α,β-eeeeeeeeeee eeeeee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8,8-Meeeeeeeeeeeee Meeee eeee e Meeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee Meeeeeeeeee ee eee 8-Meeeeeee[‌888‌]

‌Meeeeeeeeee 888‌

Meeeeeeeeeee Meeeeeeeee

8,8,8-Meeeeeeeeeeeeeeee Meeeeeeeeeeeeeeee (‌88‌, M = MM8); Meeeeee Meeeeeeee:[‌888‌,‌888‌,‌888‌]

M eeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (888 e, 8 eee) eee eeeeeeeeeeee (88 eM, 8.8 eee) eee eeeeeeee ee eeee eeeeeee, eeee eeeeee eee eeeeeee eeeeeeee eeeee eeeeeeee eeee 88% MMM8 ee Me8M (888 eM) eeeeee 88 eee. Meeee eeeeeeeee eee 8 e eee eeeeeeee eee 88 e ee eee eeeeeeeeeeee, eee eeeeee eeeeeeee eeee eeeeeeee ee eeeeeeeeee eee eeeeee eeee Me8M. Meee eee eeeeeeee, e eeeeee eeee eee eeeeeeee ee eeeeeeee eeee Me8M; eeeee: 888 e (88%). Meeeeeeeeeeeeeeee (MeMM ee 8,8-eeeeeeeeeeeeee) eeee eee eeee eeeeeee; eeeee: 88%; ee 888°M.

8,8,8-Meeeeeeeeeeeeeeee Meeeeeeeeeeeeee (‌88‌, M = MMM8); Meeeeee Meeeeeeee:[‌888‌]

Me e 8-M eeeee eeee eeeeeeeeee eeeeeee, eeeeeeee eeeeeeeeeee, eeeeee eeeeeeeee, eee eeeeeeee eeeeee, eeee eeeeee 8,8-eeeeeeeeeeee-8-ee-8-eee (888 e, 8 eee) eee eeeeeeeeeeee (88 eM, 8.8 eee). Mee eeeeeee eee eeeeee ee 88°M ee eeeeee e eeeeeeeeeee eeee, eee eeeeeee eeeeeeee eeeeeee 88% M8MM8 (88 eM, 8 eee) eee eeeee eeeeeeee ee eeee e eeee eeee eee eeeeeeeeeee eeeeee ee 888–888°M. Meee eeeeeeee eee eeeeeeeee eee 88 eee ee 888–888°M, eee eee eeeeeee eee eeeeeee ee eeee ee 88–88°M. Meeeeee (8 M) eee eeeee eeeeeeeeee eeeeeee eee eeeeeeeee eee eee eeeeeee eee eeeeeee eee 88 eee eeeee eee eeeeeee eeeeeee ee. Mee eeeeeeeeeee eeeeee eeeeeee eee eeeeeeee ee eeeeeeeeee eee eeeeee eeeeeeeeee eeee eeeeeee; eeeee: 888–888 e (88–88%). M eeee eeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM); ee 888–888°M.

Meee eee eeeeeeeee eeee ee eeee eeee eee eee eeeeee eee eeeeeeeeeeeee eee eeeeee ee eeeeeeeee eeee e eee. ee eeee ee MeM ee eee eeeeeeee ee MeMMM8, ee eee eeeeee eeeee ee eeeeeeeee eeee eeeee MMeM8, MMM8, ee MMM8.

8-Meeee-8,8,8-eeeeeeeeeeeeeeeee Meeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

Meeeee M (8,8-eeeeeeeeeeee-8-ee-8-eee ee eeeeeee eeeeeeee): 8,8-Meeeeeeeeeee-8-ee-8-eee (88.8 e, 888 eeee) eee eeeee eeeeee eeeeee (88 eeee) eeee eeeeee eeee MM8•MMe8 (88 eM) eee 8 e ee 888°M eeeee eeeeeeee. Meeee eeeeeee, MeMM (88 eM) eee 88% MMM8 (88 eeee) eeee eeeee eee eee eeeeeee eee eeeeee ee 8°M. Mee eeeeeeeeeee eee eeeeeeee ee eeeeeeeeee eee eeeeee eeee Me8M.

Me eeeeeeeee MM8•MMe8 eee MMM8 ee ee eeeee MeMM eeee ee MMeM8, eeeeeeee eeee 88% MMeM8 eee eee eeeeeeeeeeeee eeeeee ee Me8M (ee eeeeeeeee eeee 88% MMM8), eee eeeeeeeeee ee eeeeeeeee eeeee, eee eeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeeeeeee eee ee eeeeeeee.

Meeeee M (eeeeeeeeeeeeeeeeee eeeee ee eeeeeee eeeeeeeee): M eeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (8.88 e, 88 eeee), eeeeee(eee) eeeeee (88 eeee) eee MeM (eeee MeM8, MM8, ee MM8 eeeee) ee MeMM (88 eM) eee eeeeeeee eee 88 eee. Meeee eeeeeee, Me8M eee eeeee eee eee eeeeeeeeeeee eeeeeeee eeee eee eeeeeeee ee eeeeeeeeee eee eeeeee eeee Me8M.

8,8,8-Meeeeeeeeeeeeee Meeeeeeeeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

M 88% eeeeeeee eeee ee MMM8 (8.8 eeeee.) eee eeeee ee 88°M eeee 8 eee ee e eeee ee eee 8,8-eeeeeeeeee-8-ee-8-eee eeeeeeeeee (Me8MMMMMMMe8, 8.8 eeeee) eee eeee eeeeee eeeeee (Me8MMMe, 8 eeeee) ee 8,8-eeeeeeeeeeeeee (888 eM/eeeee.). Meeee eeeeeeeee eee 8 e, eee eeeeeee eee eeeeeee ee eeee eee Me8M (eeeeeeeee eeeeee) eee eeeee. Mee eeeeeee eeeeeeeee ee eee eeee eee eeeeeeeeeeeeee (MeMM).

8,8-Mee(eeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeeee Meeeeeeeeee:[‌888‌]

88% Me MMeM8 (8.88 e, 88 eeee) eee eeeee eeeeeeee ee 88°M ee e eeeeeee eeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee (8.88 e, 88 eeee) eee 8-(eeeeeeeeeeeeeeeee)-8-eeeeeeeeee-8-ee-8-eee (8.88 e, 88 eeee) eee eee eeeeeeee eee eeeeeeeee eee 8 e ee 888°M. Meeee eeeeeee, Me8M (888 eM) eee eeeee; eee eeeeee eeeeeeeeeee eee eeeeeeee eee, eeeeee eeee Me8M, eee eeeeeeeeeeeeee (MeMM) ee eeee eeeeee eeeeeeee; eeeee: 8.8 e (88%); ee 888°M.

8,8,8-Meee[8-(eeeeeeeeeeeeeeeeee)eeeeee]eeeeeeee Meeeeeeeeee:[‌888‌]

Me e 888-eM 8-eeeeee eeeee-eeeeeeee eeeee eeee eeeeeee, eeeeeeee eeeeee, eee eeeeee eeeeeeeee, e eeeeeee ee 8,8-eee[8-(eeeeeeeeeeeeeeeeee)eeeeee]eeee-8-ee-8-eee (8.88 e, 8.8 eeee) eee 8-(eeeeeeeeeeeeeeeeee)eeeeeeeeeeee (8.88 e, 8.8 eeee) eee eeeeeee ee 888°M eeeee e eeeeeeeeeee eeee eee eeeeee. Meee 88% MMeM8 (8.88 e, 8.8 eeee) eee eeeee eeeeeeee eee eeeeeee eee eeeeeeeee eee 8 e. Meeee eeeeeee, Me8M (88 eM) eee eeeee, eee eeeeeeeeeee eee eeeeeeee eee, eeeeee eeee Me8M, eee eeeeeeeeeeeeee (eeeeeee MeMM) ee eeee eeeeee eeeeeeee; 8.88 e (88%); ee 888–888°M.

Meeeeeee Meeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eee eeeeeeeeeee eeeeee (888 eeee) eee ee eeeee eeee eeeeee (88 eeee) ee e eeeeeee eeeeee (888 eeee) eee eeeeee eeeee eeeeeeee eeee MM8•MMe8 (888 eeee) ee eeee eee eeeeeeeeeeeee eeeeee ee 88% MMeM8 ee MeMM. Meee eee eeeeeee eee eeeeee, eeeeeee eeee Me8M (888 eM), eee eeeeeeee ee eeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeee (MeMM, MeMM/eMeMM, MeMM, eMeMM, ee MeMM ee eeee eeeee eeee eeeee Me8M).

8-eeee-Meeee-8,8-eeeeeeeeeeeeeeee Meeeeeeeeeeeeeeeee ‌888‌ (M8 = Me; M = MeMe8); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee 8,8-eeeeeeee-8-eeeeeeeeee-8-ee-8-eee (8 e, 88.8 eeee) eee eeeeeeeeeeee (M8 = Me; 8 eM, 88 eeee) ee Me8M (8 eM) (8 e, 88 eeee) eee eeeeeeeee eeeee eeeeeee eeeeeeee, eeeee MeMe8. Mee eeeeeee eeeeee eeee eee eeeeeeee eee eeeeeeeee eee 88 eee. Me eeeeeee, eee eeeeeeee eeeeeeeeeeeeeeeeee eeeeeeeeeeee, eee eeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM eee eeee eeee Me8M; eeeee: 8.8 e (88%); ee 888–888°M. Me eeee eeee eee eeeeeee eeeeeeee eee eeeeeeee eee eeeeee eeeeee.

8-eeee-Meeee-8,8-eeeeeeeeeeeeeeee Meeeeeeeeee ‌888‌ (M8 = Me; M = MeM8); Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeee-8-eeeeeeeeee-8-ee-8-eee (88 e, 888 eeee) eee eeeeeee ee 888°M eee 8 e eeee eeeeeeeeeeee (8 e, 88 eeee) eee 88% MMeM8 (8 e, 88 eeee). Meeee eeeeeee, Me8M (888 eM) eee eeeeeeeeee eeeee. Mee eeeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88.8 e (88%); ee 888–888°M.

8,8-Me-eeee-eeeee-8-eeeeeeeeeeeeee Meeeeeeeeee (‌888‌, M8 = e-Me; M = MeM8); Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeee-8-eeeeeeeeee-8-ee-8-eee (8.8 e, 88 eeee) eee e-MeMMMe (8.8 e, 88 eeee) eeee eeeeee eeeee eeeeeeee ee 888°M eee 8 e eeee 88% MMeM8 (8.8 e, 88 eeee). Meeee eeeeeee, MeMM (88 eM) eee eeeeee eeeeee (88 e) eeee eeeee, eee eee eeeeeee eee eeeeeeee eee 8 e. Meeee eeeeeeeeeee eee MeMM, eee eeeeeee eee eeeee ee ee eeeeeee (88 eM) eee eeeeeeee. Mee eeee eee eeeeeeeeeeee eeee Me8M; eeeee: 8.8 e (88%); ee 888–888°M (MMM8M).

8,8-Me-eeee-eeeee-8-eeeeeeeeeeeeee Meeeeeeeeeeeeeeeeeeeeeeee (‌888‌, M8 = e-Me; M = MMe); Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeee-8-eeeeeeeeee-8-ee-8-eee (8.8 e, 88 eeee), MeMM (8.8 e, 88 eeee), eee e-MeMMMe (8 e, 88 eeee) eeee eeeeeee ee 888°M eee 8 e, eeee eeeeeeee ee MeMM (88 eM) eee 88 eee; Me8M (88 eM) eee eeeee eee eee eeeeeee eee eeee ee 8°M eee 88 e; eeeee: 88%; ee 888–888°M.

8-eeee-Meeee-8,8-eeeeeeeeeeeeeeee Meeeeeeeeeeeeeeee (‌888‌, M8 = Me; M = MM8); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

Me e eeeeeee ee eeeeeeeeeeee (8.8 e, 88 eeee) eee 8,8-eeeeeeee-8-eeeeeeeeee-8-ee-8-eee (88.8 e, 888 eeee) eee eeeee MM8•MMe8 (88 e, 888 eeee), eeee eeeeeee ee 888°M eee eeeeeee eee 8 e. Me eeeeee Me8M eee eeeeeeee eeee eeeeeeeeeeee eee eee eeeeeeee ee eeeeeeeeee; eeeee: 88.8 e (88%).

8,8-Me-eeee-eeeee-8-eeeeeeeeeeeeee Meeeeeeeeeeeeeeeeeeeeeeee (‌888‌, M8 = e-Me; M = MMe); Meeeeee Meeeeeeee:[‌888‌]

eeee-Meeee eeeeee eeeeee (88.8 e, 8.8 eee), e-MeMMMe (88 e, 8.8 eee), eee MeMM (88 e, 8.8 eee) eeee eeeeee ee 888°M eee 8 e. Mee eeeeeeee eeee eee eeeeeeeeeeee eeee Me8M eee eeeeeeeeeeeeee (MeMM) ee eeeeeee; eeeee: 88.8 e (88%); ee 888–888°M.

8-eeee-Meeee-8-(8-eeeeeeeeeeee)-8-eeeeeeeeeeeeee Meeeeeeeeeeeeeeeeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

8-(8-Meeeeeeeeeee)-8,8-eeeeeeeeeeee-8-ee-8-eee (8.8 e, 88.8 eeee), eeeeeeeeeeee (8.8 e, 8.8 eeee), eee MeMM (8.8 e, 88.8 eeee) eeee eeeeee ee 888°M eee 8 e ee eeee eee eeeee eeeeeeee ee eeeeee; eeeee: 88%; ee 888–888°M.

8-Meeee-8-eeeeee-8,8-eeeeeeeeeeeeeeee Meeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

Meee e eeeeeee eeeeeeeeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (8.88 e, 88 eeee) ee Me8M (88 eM), e eeeeee eeee ee 88% MMeM8 (8.8 e, 88 eeee) ee Me8M (8.8 eM) eee eeeee eeeeeeee. Meee eeeeee-8-eee (8.88 e, 88 eeee) eee eeeee. Meeee 8 e eee eeeeeeeeeee eeee eee eeeeeeee ee eeeeeeeeee, eeeeee eeee Me8M, eee eeeeeeeeeeeeee (MeMM); eeeee: 8.88 e (88%); ee 888–888°M.

8-(8-Meeee-8-eeeee)-8,8-eeeeeeeeeeeeeeee Meeeeeeeeee (‌888‌, M = MeM8; M = Me); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (8.8 e, 88 eeee) ee Me8M (88 eM) eee eeeeeee ee 8°M eeee 8-eeeee-8-eeeeeeeeeee (8.8 e, 88 eeee) eee 88% MMeM8 (8 eM). Mee eeeeeeeeeeee eeeeeeee eeee eeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88%; ee 888–888°M.

8-(8-Meeee-8-eeeee)-8,8-eeeeeeeeeeeeeeee Meeeeeeeeee (‌888‌, M = MeM8; M = Me); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeeeeeeeeeeeeeeeeeeeeeeeeee (8 eeee) eee eeeeeeeeeeee (8 eeee) eeee eeeeeeeee ee Me8M (88 eM) eee eeeeeee eeeeeeeee eeeee eeeeeeee eee eeeeeee ee −8°M eeee e eeee eeee ee 88% MMeM8 (8 eM) ee Me8M (8 eM). Mee eeeeeee eee eeeeeee eeee eee Me8M (888 eM), eee eeeeeeeeeeee eeeeeeee eeee eeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 8.888 e (88%).

8-(Meeeeeeeeeee-8-ee)-8,8-eeeeeeeeeeeeeeee Meeeeeeeeee; Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeeeeeee-8-ee-8-eee (88.88 e, 888 eeee) eee eeeee eeee 8 e eeeee eeeeeeee ee 8-eeeeeeeeeeeeeeeeeee (8 e, 88 eeee) ee 88% MMeM8 (88 eM) eee MeMM (888 eM) ee 888°M eee eee eeeeeeee eee eeeeeeeeee ee eeee eeeeeeeeeee eee 8 e. Meeee eeeeeee, Me8M (888 eM) eee eeeee. Mee eeee eeeeeeeeeee eee eeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM (8 × 88 eM) ee eeee eeeeee eeeeeee; eeeee: 88%; ee 888–888°M (eee; MeMM).

8,8′-(8,8-Meeeeeeee)eee(8,8-eeeeeeeeeeeeeeee) Mee(eeeeeeeeeeeeeeeee) (‌888‌):[‌888‌]

8,8-Meeeeeeeeeeeeee (8 eeeee) eee eeeeeee eeee (eeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee (8 eeeee) ee MMMM ee 88°M eee 8 e, eeeeeeeee eee eee-eeeee; eeeee: 88%. Mee eeeeeeeeee Meeeeee eeeeeeee ee eeeeeeeeeeee eee eeeeeeeee eeee e-MeMM ee e-MeMM/MMM (8:8) ee ee eee 8 e; eeeee: 88%. Mee eeeeeeeeeeeeeee eeeeeeeeeee eee eeeeeeee eeee 8,8-eeeeeeeeeeee-8-ee-8-eee (8 eeeee) ee eeeeeee eeeeeeee eee MM8•MMe8 (88 eeeee) ee 888°M eee 8 e; eeeee: 88%.

8,8-Meeeeeee-8-[8-(8-eeeeeeeeeeee-8-ee)eeeeee]eeeeeeee Meeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeeeeeee-8-ee-8-eee (88 eeee) eee 8-(8-eeeeeeeeeeee)-8-eeeeeeeeeeeee (‌888‌; 88 eeee) ee Me8M (88 eM) eee eeeeee eeeeeee eeee 88% MMeM8 (8 eM, 88 eeee) eeeeeee eee eeeeeeeeeee ee 888°M, eeee eeeeeeee eee eeeeeee ee eeee ee 88°M eee 8 e. Meeeeeee eeeeeeee ee MeMMe (888 eM) eeeeeeeeeeee eee eeeeeeee eeee ‌888‌. Me eee eeeeeeee ee eeeeeeeeee, eee eeeeeeee eeee MeMM/MeMMe/Me8M; eeeee: 88%; ee 888°M.

8,8-Meeeeeee-8-(8-eeeeeeeeeee)eeeeeeee Meeeeeeee Meeee Meee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

Meeeee 8-eeeeeeeeeeeeeeeeeeeeee (8.8 e, 88 eeee), 8,8-eeeeeeeeeeee-8-ee-8-eee (88.8. e, 88 eeee), eee 88% MMeM8 (88 eM) eeee eeeeee ee 888°M eee 8 e eeee eeeeeeee. Mee eee eeee eeeeeee eee eeeeeee eeee MeMM (888 eM) eee eee eeee eee eeeeeeee eee 88 eee, eeeeee, eee eee eeeeee eeeeeeee eeee eeeeeeee ee eeeeeeeeee eee eeeeee eeee eee MeMM (888 eM). Mee eeeeeeee eeeeeeee eee eeeeeeee ee MeMM (888 eM), eeeeee eee eee eeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeeee, eeeeeeeeee eeee eeee M8M (888 eM), eeeeeeee ee eeeeeeeeee eeeee, eee eeeeeeee ee eeeeeee. Mee-eeeeeeeeeeee eee eeeeeeeeeeeeeeee eeeeeeeee eee eeeeeeeeee eeeeeeeee ee e eeeeeeeeeee. Meeeee eeeeeeee eeee eeeeee eeee eee eeeeeee eee eeeeeeeeeeee eeee eeeee eeeee. Mee eee eeeeeeee eeeeeeee ‌888‌ eee eeeeeeee; eeeee: 8.8 e (88%); ee 888°M (eee).

References

Meeeeee Meeeeeeeeee

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