Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
29.8.1.1.1.1 Variation 1: From Reactions of Carbonyl Compounds with 1,3-Diols

DOI: 10.1055/sos-SD-029-00478

Kouklovsky, C.Science of Synthesis, (200729491.

The direct condensation of carbonyl compounds (aldehydes or ketones) with 1,3-diols is the classical method for the preparation of 1,3-dioxanes. The reaction follows the general mechanism for acetal formation, with acidic catalysis (Scheme 7). Since water is evolved in the reaction, its removal from the reaction is necessary in order to shift the equilibrium to the formation of the dioxane.

Meeeee 8 Meeeeeeee ee 8,8-Meeeeeee ee Meeeeeeeeeee ee Meeeeeee Meeeeeeee eeee 8,8-Meeee

Meeeeeee eeeeeeee eee eeeeeeeeee eeee eeee eeeeeeeee eee eeee eeeeeeee. Meeee eeeeeee eee ee eeeeeeeee eeeeee ee eeeeeeeeee eeeeeeeeeeee (MeeeMeeee eeeeeeeee) eeee eeeeeee ee eeeeeee, ee eeeeeeee ee eeeeeeeee eeeeee, ee ee eee ee e eeeeeeeeeee eeeeeee [eeeeeeeee eeeeeee, eeeeee(MM) eeeeeee, eeeeeee eeeeeee, eeeeeeeeee eeeeeeeee, ee eeeeeeeee eeeeeeeeeeee eee eeeeeeeee eeee eee eeee eeeeeee]. Meeee eeee ee eeeeeeeee eeeeeee eeeeeeeee eeeee eeee ee eeeeeeeeeeee eeee, eeeeeeeeeee eeee, ee eeeeeeee eeee, eeeeeeeeee eeeee eeee ee eeeeee eeee, eeeeee eeee, ee eeeeeeeeeeeeeee eeee, ee eeeeeeee eeeee eeee ee 8-eeeeeeeeeeeeeee eeee, eeeeeeeeeeeeeee eeee, ee eeeeeeeeee 8-eeeeeeeeeeeeeeee. 8-Meeeeeeeeeeeeee eeee, ee eeeeeee ee eeeeeee eeeeeeee eeee eeeeeeeeee eeeeeeeeeeee ee eee eeee eeeeeeeeee eeee eeeeee eee eeeeeeee eeeeeeeeee. Meeee eeeee, eeeeeeeee eeee(MM) eeeeeeee, eeeeeeee(MM) eeeeeeee, ee eeeeeeee(MMM) eeeeeeee, eee eeee eeeeeeeee eee eeeeeee eeeeeeeee.

Mee eeeeeeeeee ee eeeeeeeee eee eeeeeee ee 8,8-eeeeeeee ee eee ee eeeeee ee eeeee eeeeeeeeee ee 8,8-eeeeeeeeee, eeeee 8,8-eeeee eee eeee eeeeeeee eeee 8,8-eeeee ee eee eeeeeeeeeeeee eeeeeeee. Meeeeeeeeeee, eeee e eee eeeeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeeee eeee eeee eeeeeee ee eee eeeeeeeee ee 8,8-eeeeeeee.

Mee eeeee ee eee eeeeeeeeee eeeeeeee eeeeeee eeeeeeee eeee eee eeeeee ee eeee eeeeeeee. Meeeeee-8,8-eeee (8) ee eeee eeeeeeee eeee eeeeee-8,8-eeee eee eeeeeeeee eeeee eeeee eeeeee eeeee eee eeee eeeeeeee eeeeeeeeee. Meeeeee, 8,8-eeeeeeeeeeeeeee-8,8-eeee (8) ee e eeeeee eeeeeeee 8,8-eeee eeeee ee eeeee eeee eee eeeeeeee eeeeeeeeee, eeeeeeeeee eee eeeeeeee eeeeeeeeee; eeeeeeee, eeee 8 ee e eeeeeeeeeee eeeeeeee. Mee eeeeeeee eeeee ee eeeee eeeee eeee eeeeeeee eeeeeeeee eeee eeee eeeeeee.[‌88‌] Meeeeee eeeeeeeee 8,8-eeee eee 8,8-eeeeeee eeeeeeeee ee eee eeeeee, M8-eeeeeeeee eeeeeee-8,8-eeee (8) (Meeeee 8).

Meeeee 8 Meeeeeeee 8,8-Meeee eee eee Meeeeeeee ee 8,8-Meeeeeee

Mee eeeee ee eeeeeeeeee eee eeeeeeee eeeeeeeee ee eee eeeeeeeee ee eeeeeee eeeeeee eeeeeee eeeee: (8) Meeeeeeee eee eeee eeeeeeee eeee eeeeeee; eeee eeeeeeeeeee ee eeee eeeeee eee eee eeeeeeeee ee 8,8-eeeeeeee eeee eee eee eeeeeeeee ee 8,8-eeeeeeeeee. (8) Meeeeeeee eeeeeeee eeeeeeeee eee eeee eeeeeeee eeee α,β-eeeeeeeeeee eeee. (8) Meeeeeee eeeeeeeeee eee eeee eeeeeeee eee eeeeeeeee eeee eeeeeeeeee. (8) Meeeeeee-eeeeeeeeeee eeeeee ee eeeeeeee eeeeeeeee eee eeeeeee eeeeeeee eeeeeeeeeeeee, eeeeeee eeeeeeee-eeeeeeee eeeeee eeeeeeeeee eee eeeeeeee.

Meeeeeeeeee eeeee eeeeeeeeee, ee ee eeeeeeee ee eeeee eee eeeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeeee. Meee ee eeeeeeeeee eeeeeee ee eee eeeee ee eeeeeee eeeeeeeee: eeeeeeeee eeeeeeeeeeeee ee 8α-eeeeeeeeee-8,88-eeeee (8), ee eeeee eee 8-eeeeee ee eeee eeeeeeee eeee eee 88-eeeeee, ee eeeeeeee ee eeeeeeeee eeee 8,8-eeeeeeee- ee 8,8-eeeeeeeeeeeeee-8,8-eeee ee eeee eee eeeeeee 888 (Meeeee 8).[‌88‌] Mee eeeeee eeeee eee eeeeeeeeee ee eeeeeeeeeee eeeee 88 eeeeeeeeeee ee eee 8,8-eeee. Meeee eeeeeeee eeee eeeeee eeeeeeeeeee eeee eeeeeeee eeeeee. Me eeeeee ee eeeeeee eee eeee eeeeeee-8,8-eeee ee eee eeeeeeeeee eee eee ee eeeeeee eeeeee eeeeeeeeee.

Meeeee 8 Meeeeeeee Meeeeeeeeeeee ee 8α-Meeeeeeeee-8,88-eeeee eeee 8,8-Meeee[‌88‌]

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

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee ee Meeeeeee ee Meeeeeeee ee Meeeeee eeee 8,8-Meeee ee eee Meeeeeee ee 8-Meeeeeeeeeeeeee Meee ee Meeeeeeeee 8-Meeeeeeeeeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88M

M8 M8 M8 M8 Meee (eeeee) Meeeeeeeee Meeee (%) Mee
Me Me M M 8.8 eeeeeee, 88e 88 [‌88‌]
MMMe Me M M 8 eeeeeee, 88e 88 [‌88‌]
MMMe Me M M 8 eeeeeee, 88e 88 [‌88‌]
Me M MM8Me M 8.8 eeeeee, 8e 88 [‌88‌]
(MM8)8Me Me Me Me 8.8 eeeeeee, 8.8e 88 [‌88‌]
Me M M 8 eeeeeee, 88e 88 [‌88‌]
Me Me 8.8 eeeeeee, 8e 88 [‌88‌]
Me Me 88 eeeeeee, 88 e e [‌88‌]
M M M 8 eeeeeee, MMM, 88e 88 [‌88‌]
M M eeeeee eeeeeee, 88e 88 [‌88‌]

e Meeee eee eeeeeeee.

Meeeeeeeeee 88M

M8 M8 Meeeeeeeee Meeee (%) Mee
8 (8.8 eeeee), eeeeeee, 88e 88 [‌88‌]
Me Me 8 (8 eeeee), eeeeeee, 88e 88 [‌88‌]
(MM8)8Me Me 8 (8 eeeee), eeeeeee, 88e 88 [‌88‌]

Meeeeee eeeeeeeeee eeeeeeeeeeee, eeeee eeeeeee eee eeee ee eeeeeeeeeeee ee eeeeeeee ee eeeeee eeeeeeee. Meee eeeeeeeeeeee eeeee eeeeee eeeeee eeeeeeee eeeeeeeeee. Meeeeeee eeeeeeeee eeeeee ee eeeeee(MM) eeeeeee eee eeeeeeeee, eeeee eeeeee eeee ee eeeeeeee ee eeeeeeeee eeeeeeeeeeee eee eeee eeeee eeee ee eeeee eeeeeeeeee ee eeeeeeeeeeeee eeeeeeeee.[‌88‌,‌88‌] Meee eeeee eeee eeeee ee eeee ee eeeee eee ee eeeeeee, eee eeeeeeeee eeeeeeeeee ee eeeee eee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeee. Meeeeeee, eee eeee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee ee eee eeeeeee ee eeeee eeeeeeee: ee ee eeeeee eeee eeeeeee eeeeeee eee eeeee eeeeee, eeeee eee eeee eeeeeeeee eeee eee eeeeee eeeeee. Meee ee eeeeeeeee ee eeeeeeee eeeeeeeeeeeee eeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeee Meeeeeeee eee eee Meeeeeeee ee 8,8-Meeeeeee ee eee Meeeeeee ee Meeee Meeeee[‌88‌]

Meeeeeee eeeeeeee ee 8,8-eeeeeee eeeeeeeee eeee eeeeeee-8,8-eeee (8) eee eeeeeee-8,8-eeee (8) eee eeeee ee Meeeee 88 (e.e., 88 eeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee ee Meeeeeee ee Meeeeeee Meeeeeeee eee 8,8-Meeee eeee 8-Meeeeeeeeeeeeee Meee eee ee Meeee Meeee[‌88‌,‌88‌]

Meeee eeee eeeeeeeee eee eeee eeeeeeee eeee eee eee eeeeeeeee ee 8,8-eeeeeeee, eeeeeeeeee eeeeee eeee eeeeeeeeee eeeeeee ee eeeee ee eeee eeeeee eeeeeeee. Meeeeeeee eee eeeeeeeee ee eeeeeee eeee eee ee eeee, eee eee eeee eeeeee eee eeeeeeee eeee[‌88‌] eee eeeeeeeeeeeeeee eeee.[‌88‌] Mee eeeeeeeeeeee eeeeeeeee ee eeeeeee ee eeee eeee 8-eeeeeeeeeeeeeee eeee, eeee e eee eeeee ee eee eeee eeeee eeeee ee eee eeeeeeee eeeeeee.

Meeee-eeeeeeeee eeeeeeee eeee eeee eee eeeeeee ee eeeeeee eeeeeee eee eeeeeeeee, eeeeeeee, eee eeeeeeeeeeeee eeeeeee.[‌88‌] Meee, eeeeee eeeeee ee eeeee eeee eeee eeeeee eeee eee eeeeee eeeeeeeee. Meeeeeeee 88, e eeeeeeee eeee eeeee, ee ee eeeeeeeee eeeeeeee eee eeeeee eeeeeeeee eee ee eeeeee eeeeeee eeee eee eeeeeeee eeeeeee ee eeeeeeeeee.[‌88‌] Meeeeeeeeeeee eeee Meeeeeeee 88 eee eeeeeeeee eeeeee eeeeee eee eeeeeeeee ee eeeeeee eeeeeee eee eeeeee, eeeeeeeee 8,8-eeeeeeee 88, eeeee eeee eeee eeeeeeeeee (Meeeee 88).[‌88‌] Meee eeeeeeeee eee eeee eeee eeeeeee ee eee eeeeeeeeeeeee ee eeeeeeeeeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee Meeeeeee Meeeeeeee eee Meeeeee-8,8-eeee Meeee Meeeeeeee 88 ee Meeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
Me M 88 [‌88‌]
8-MeMM8M8 M 88 [‌88‌]
8-MMM8M8 M 88 [‌88‌]
Me Me 88 [‌88‌]
Me Me 88 [‌88‌]
eMe Me 88 [‌88‌]
Me Me 88 [‌88‌]
(MM8)8 88 [‌88‌]
(MM8)8 88 [‌88‌]

Meeeeeeee eeeeeeeeeee eeeeeeeeeee [Me(M8MMe)8.8(M8MM8M8MM8M)8.8] ee e eeeeee eeeeee eeeee eeeeeee, eeeeeeeeee eeeeeeee eeee eeeeee eeeeeeee ee eeeeeeeee eeeeee; ee eeee ee e eeeeeeee eee eee eeeeeeeee ee eeeeeee eeeeeee, eeeeeeeee 8,8-eeeeeeee 88 (Meeeee 88).[‌88‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeee; eee eeeeeeee ee eeeeeee ee eeeeee eeeeeeeeee eee eee ee eeeeeeee eeeeeee eeeee eeeee eeeeeee eee eeeeee. Meeeeee, eee eeeeeeeee ee 8,8-eeeeeeee ee eeeeeee ee eeeeeeeee ee eeeeeeeeeee eeeeeee.

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee Meeeeeee Meeeeeeee eee Meeeeee-8,8-eeee Meeee Meeeeeeee Meeeeeeeeee Meeeeeeee ee Meeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meee (e) Meeee (%) Mee
Me M 8 88 [‌88‌]
(MM8)8Me M 8 88 [‌88‌]
Me M 8 88 [‌88‌]
8-MMM8M8 M 8 88 [‌88‌]
8-M8MM8M8 M 8 88 [‌88‌]
Me Me 88 88 [‌88‌]
(MM8)8 8 88 [‌88‌]

Meee eeee eeeeeeeeee eee 8,8-eeeeeee (eee eeeee eeeeee) eeeeeeeee eee eeeeeeee eeee eeeeeeee eeeeee eee ee eee eeeeeeee (Meeeee 88).[‌88‌] Meeeeeeee ee eeeeeeeeee eeeeee eee eeee (eeeeeeeeeee)eeeeeeeeeeeeeee, eeeeeeee ee eeeeee eeeeeeeee, eeeee ee eeeeeeeee eeeeee eeeeeee eeeee eeeeeeeee eee eeeeeeeee ee eeeeeee eeeee eeee eeee eeeeeeeeee. Mee eeeeeeeee ee 8,8-eeeeeeee eeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeeeeee. Meee eeeeee ee eeeeeeeeee eee eee eeeeeeeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeee; eee eeeeeeee ee eeeeeeeeeee ee eeeeeee eee eeeeee eeeee eeeeeee eeeeeeee.

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee Meeee Meeeeeeeeeeeeee Meeeee Mee ee e Meeeeeee[‌88‌]

Me eeeeeeee eeeeee eee eeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeee eeeee eeeeeeeeeeeeeeeeee eeeeeeeeee ee ee eeeeeeeeeee eee eeee-ee-eeeeee eeeeeeeee ee eeeeeeee eeeeeee. Meeeee eeeeeeeeeeeeeeeeee eeeeeeeeee eee eeeeeeee eeeeeeeeeeee eeeeeeeee eeeee eeeeeeeeee ee eeeeeeee eeeeeee, eeeee eeeeeeeee eeeeee eeeeeeeee eeeee eeee eeee eeeeeeeeee. Meee eeeeeeee eee eeee eeeeeee ee eee eeeeeeeee ee eeeeeee 8,8-eeeeeeee 88 (Meeeee 88) eee ee eeee eeeeeeeee eee eee eeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeeee (Meeeee 88).[‌88‌] Meeeeeeeee, ee eeee eee, eeeeee eeeeeeee eeeeeeeeeeee eee eeee eeeeeeeeeeee eeeeeeeeeee eeee eee eeeeeeeeeeeee 8,8-eeeeeee ee eeee eeeee.

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee ee eee Meeeeeee ee Meeeeeeeeeeeeeeeee Meeeeeeeee eee Meeeeeee Meeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meee Meeee (%) Mee
Me M 8eee 88 [‌88‌]
8-MeMM8M8 M 8eee 88 [‌88‌]
8-M8MM8M8 M 8.8e 88 [‌88‌]
8-MMM8M8 M 8.8e 88 [‌88‌]
8-MMM8M8 M 8eee 88 [‌88‌]
8-Me-8-M8MM8M8 M 88e 88 [‌88‌]
8-eeeee M 8eee 88 [‌88‌]
MM=MMMe M 88eee 88 [‌88‌]
Me Me 8eee 88 [‌88‌]
Me Me 88e 88 [‌88‌]
8-MMMMMMM8M8 M 8eee 88 [‌88‌]
8eee 88 [‌88‌]
8eee 88 [‌88‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeeee ee eee Meeeeeee ee Meeeeeeeeeeeeeeeee Meeeeeeeee eee Meeeeeee Meeeeeeeeeee[‌88‌]

Meeeeee eeeeee eeeeeeee, Meeee eeeee eee eeee eeeeeeeee eeeeeeeeeee eeeeeeeee ee eeeeee eeeeeeeee. Meeee eeeeeeeee eee eeeee eeee ee eee eeeeeeee ee eeeee eeeeee, eeeeeeeee eeeeeeee eeeeeeee eeeeeeeeeeeee. Meeeeee eee eeeeee ee Meeee eeeee eeeeeeeee, eeee e eee ee eeee eeee eeee eeeeeee ee eee eeeeeeeee ee 8,8-eeeeeeee. Meeeeeee(MMM) eeeee eeee ee eeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeeeee eeee eeee eeeeeeee ee eeeeee eeeeeeee eeeeeeeee eee eee eeeeeeeee ee 8,8-eeeeeeee eeee 8,8-eeeeeeeeeeeeeee-8,8-eeee (8) ee eeeeeee-8,8-eeee (8) eeee eeeeeeeee eee eeeeeee.[‌88‌,‌88‌] Meeeeeee eeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeeeee ee eeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeeeeee (Meeeee 88),[‌88‌] eeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeee eeeeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee ee eee Meeeeeee ee Meeeeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeeeee eee Meeeeeeee Meeeeeeeeeee[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee ee eee Meeeeeee ee Meeeeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeee[‌88‌]

Me eee eeeeee eee eeee eeee eeeeeeeeee ee eee eeeeeeeee ee eeeeeee, eeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeee eeee eeeeeeee ee eeee eeeeeeeee eeeeeeeee eee eee eeeeeeeee ee 8,8-eeeeeeee eeeeeeee eeee eeee-eeeeeeeee eeeeeeeeee. Meeeee, Me+ ee eee eeeeeeee ee ee eeeee eeeee ee e eeeeeeeeee eeeeeee eee eeeeee eeeeeeeee. Mee eeeeeee ee eeeeeeeeeeeee eeeeeee eeee eeee eeee: M-eeeeeeeeeeeeeeee[‌88‌] ee 8,8,8,8-eeeeeeeeeeeeeeeeeee-8,8-eeeeeee (88).[‌88‌] Mee eeeeee eeeeeee (eeeeeeee ee eeeeeeeeeee ee eeeeee) ee ee eeeeeeeeeee eeee eee eeeeeeeee eeeee eee eeeeeeeee eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeee Meeeeeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeee-8,8-eeeeeee[‌88‌]

Mee eeeeeeee ee eeeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeee eeee eeeeeee-8,8-eeee (8) ee eee eeeeeeee ee eeeeeeee eeeeeeeeeeee eeeee eee eeeeeeeeeeeee 8,8-eeeeeeee 88 ee eeee eeeeeeeeeee (eeee M-eeeeeeeeeeeeeeee) ee ee 88°M (eeee 8,8,8,8-eeeeeeeeeeeeeeeeeee-8,8-eeeeeee) eeeee eeee eeee eeeeeeeeee (Meeeee 88).[‌88‌,‌88‌] Meeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeeee ee eeeeeeee eeee eeee eeeeeeeee eee eeeeeeee eeeeeeeeee. Meee-eeeeeeeee eeeeeeeeee eeeeee eeee ee eeeee eeeeee ee eeeeeeeeeeeeeeeee eeeeee eee eeeeeeeeee eeee eee eeeeeeee eeeeeeeeee. Me eee eee eeeeeee, eeeeeeeeee eeeeeeeee ee eeeeeee eeee eee eeee eeeeee.

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee ee eee Meeeeeee ee M-Meeeeeeeeeeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeee-8,8-eeeeeee eee Meeeeeee Meeeeeeeeeee[‌88‌,‌88‌]

Meeeeeee eeeeee α,β-eeeeeeeeeee eeeeeeeee eee eeeeeee eee ee eeeeeeeee eeee eeeee eeeeeeeeeeeee 8,8-eeeeeeee eeeee eeeeeeee eeeeeeeeee, eee eeeeeeeee ee 8,8-eeeeeeee eeee eeeeee eeeeee ee eeeeeeee ee eee eeeeeeeeee eee eee eeeeeeeeeee ee eeeeee eeee eeeeeeeee, eeeeeeeeee eeee eeeeee eeeee eee eeee. Meee eeee eeeeeeee eee eeee eeee eeeeeeeeee ee eee eeeee ee eeeeeeee.[‌88‌] Meeee eee eee eeeeeeeeee ee eeeeee eeeeee eeee 8,8-eeeee, ee ee eeeee eeeeeeeee ee eee eee eeee eeeeeeee 8,8-eeeeeeeeeeeeeee-8,8-eeee (8), eeeeeeeeee eeee eeeeeeee eeeeeeeeee. Mee eeeeeee eeeeeeeeee ee eeee 8,8-eeee eeeeee eeeeee eeeeeeeeeee eeee eeeeee eeeeeeeeee ee eee eeeeee eeeeeeeee. Meeeee eeee eeeeeeeee eee ee eeeeeee, ee eeeeeeeeeee ee eee eeeeeeeee ee eee 8,8-eeeeeee 88 eeee e eeeeeeeee eeeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee eeee e Meeeee Meeee eee 8,8-Meeeeeeeeeeeeee-8,8-eeee[‌88‌,‌88‌]

Mee eeeeeeeeee ee 8,8-eeeee ee eee eeeeeeeee eeeeeeeeeee ee 8,8-eeeeeee eeeeeeeee. Mee eeeee eee eeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeee eeee eeeeeee eeeee eee eeeeeee eee eeee eeeeeeeeee eeeeeeeeeeee, eeeeeeeeee ee eee eeeee ee eeeeeeeeeeee eeeeeeeee. Me eeeeeeeee eeeeeee ee eee eeeeeeeee eeeeeeeeee ee eee 8- eee 8-eeeeeee eeeeee ee eeeeeee (eeeeeee, eeeeeee, eeeeeeeee) ee eeeeeeeeeee, eeeeeeeeeeeeee, ee eeeeeee eeeeeee. M eeeeee ee eeee eeeee, eeeeeeeeee eeeeeeee eeeeeeeeeeee eeeeeeeeee, ee eeeeeeeee.[‌88‌]

Meeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeee ee eee eeeeeeeeeee ee eeeeeee eeeeee eeeeeeeeeeeee eeeeeee ee eee eeeeeeeee ee eeeeeee, eee eeeeeee eeeeeeee eeee eee eeeeeeee eeeeeeeeee. Me e eeeeeee eeee eee eeeeee eeeeee eeeeeeeee eeeee eeeeeeeeeeeee eeeeeee, eeeeeeeee eeeee eeee 8,8-eeeee eeeeeeeeeeeeee ee eeee 8,8-eeeeeeee, eeeeeee eeeeeee eeeee eeee 8,8-eeeee eeeeeeeeeeeeee ee eeee 8,8-eeeeeeeeee. Meeeeeeeeeeeeee ee eeeeee-eeeeeee 8,8-eeeeeeee ee eeeeeeeee ee eee eeeeeeee ee ee eeeee eeeeeeeeeee ee eee eeeeeee eeee. Meee eeee ee eeeeeeeee eeeeeeeeeee ee eee eeeeeeee ee M-eeeeeee (88) eeee eeeeeeeeeeee eee eeee eeeeeee (Meeeee 88).[‌8‌]

Meeeee 88 Meeeeeee ee M-Meeeeee eeee Meeeeeeeeeee ee Meeeeee ee ee Meeeee Meeeee[‌8‌]

Meeeeeeeeee eeee eeee, eee eeeeeeeee 8,8-eeeeeeeeee ee eeeeeeeeeeeee ee 8,8-eeeeeeee ee eeeeee eeeeeeeeeeee eee ee eeeeeeeeeeee eeee eeee eeeeeeeee; eeeeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeee eee eee eeee eeeee eeee eeeeeeeee eee eeee eeeeeee. Meeeeee, eeeeee eeeeeeeee ee M-eeeeeee (88) (eee eeeee eeeeeeeee) eeee eeeeeeeeeeee, eeee eeeeee eeeeeeeee, eeeee eee eeeeee ee 8,8-eeeeeeee 88, eeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeee eeee eeeeeeeeee eee eeeeeeeeeeee. Me eeeeeeeeee, e eeeeeeeeeee eeeeeeee ee 8,8-eeeeeee eeeeee ee eeeeeeee. Meeeee eeeeee eee eeeeee eeeeeeeeeeee eee eeeeeeee eeeee e Meeee eeee eeee ee eeee(MM) eeeeeeee ee eeeeeeee, eeee eeeeee eeeeeeeeeeee eee ee eeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-M-Meeeeeeeeee-M-eeeeeeeeeeeee eeee M-Meeeeee[‌88‌]

Meee eee eeeeeeee eeeeee ee e eeeeee ee eeeeeeeee, eee eeeeee eeeeeeee eeee eeeeee eeee eeeeeeeeeeee eeeee eeeeee eeeeeeeeee ee eeee eee 8,8-eeeeeeeeeee eeeeeeeeee ee eeee eeeee, e.e. 88 eeee 88 (Meeeee 88). Meeeeeeee eeee ee eeee(MM) eeeeeeee, 8-eeeeeeeeeeeeeee eeee,[‌88‌,‌88‌] ee eeeeee eeee[‌88‌] eee ee eeee; eeeeeeeeeeee ee eeee eeeeeeeee eeee ee eee eeeeeee eee eee eeeeeeee.

Meeeee 88 8,8-Meeeeeeeee ee Meeeee M-Meeeeeeeeee eeee Meeeeeeeeeee[‌88‌,‌88‌]

Meeeeee 8,8-eeeee eeeeeeee eeee eeeeeeeee ee eeeeeee eeeee eeeeee ee Meeee eeee eeeeeeeee ee eeee eee eeeeeeeeeeeee 8,8-eeeeeeee. Meee eeeeee eeeeeeeeee, eee eeeeeeeeeee eeeee eee eeeeeeeee ee eeeee eeee eeeeeeeeeeee eeeeeeeeee, ee eeeeeeeee eeeee eeeeeeeeeeeeee eeee 8,8-eeeee eee eeeeeee eeee 8,8-eeeee. Meee, (8M)-eeeeee-8,8,8-eeeee (88), eeeeeeee ee eeeeeeeee ee eeeee eeee, ee eeeeeee eeee 8-eeeeeeeeeeeeeeeeeee eee eeeeeeeeee 8-eeeeeeeeeeeeeeee ee eeee e eeeeeee ee eee 8,8-eeeeeee 88 (8,8-M-eeeeeeeeee) eee eee 8,8-eeeeeeeee 88 (8,8-M-eeeeeeeeee) ee e 88:8 eeeee (Meeeee 88).[‌88‌,‌88‌] Mee eeeeeeeee ee e 8,8-eeeeeeeee ee 8,8-M-eeeeeeeeee ee eee eeeeeeee. Meeee eeeeeee ee eeeeeeeeeeee eeeeee eeee e MeeeMeeee eeeeeeeee[‌88‌] ee eeee e Meeeeee eeeeeeeee eeeeeeeeee 8-Å eeeeeeeee eeeeee.[‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee (8M)-Meeeee-8,8,8-eeeee Meeee 8-Meeeeeeeeeeeeeeeeee eee Meeeeeeeee 8-Meeeeeeeeeeeeeee[‌88‌]

Mee eeeeeeeee ee e eeeeeeeeeee eeeeeeeeee ee e 8,8-eeee eeeeeeeee e eee eeeeeeeeeee eeeeee eeeeeee eee eeeeeeee eeeeeeeeeee. Meeee eeeeeee ee eeeeeeeeeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeee, eeeeee eeeeee eee eeee eeeeeeeeeee ee eee eeeeeeeeee eeeeeeee. Meeeeeee, 8,8-eeeeeeee ee eeeee eee eee eeeeeeeeeeee ee eee eeeeeee eeee eee ee eeeeeeeeee eeeeeeeee eee eeee eeeeee. Meeeeee, eeee eeee eee ee eeeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeee eeeeeee eeee eeeeeee eeeeee ee ee eeeee eeeeeeee eee eee eeeeeee eeeeee eeeeee eeeee. Meee eeeeeeee eee eeeeeeeeee eeeeeeeeeee ee eee eeeeeeee ee M-eeeeeeee (88) eeee eeeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee Meeeeeeee ee e 8,8-Meeeeee eeee M-Meeeeeee eee Meeeeeeeeeee[‌88‌]

Meeeeeeee 8,8-eeeee eeee eeee-eeeeee eeeeeeeeee eeeeee eee ee eeeeeeeeeee eeee eeeee eeeeeeeeeeeee 8,8-eeeeeeee eeee ee eeee eeeeeeeeeeee ee eee (ee eeee) eeeeeee eeeee(e), eeeeeeee ee eeeeeeeeeeeee. Meee-eeeeee eeeeeee eeeeeeeeee eeeeee eeeeeee eeeeeeeeeeeeee, eeeeeeeeeeeee, eeee-eeeeeeeeeeeeeeeeee, ee eeeeeeeeeeeeeeeee eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee eeee e Meeeeeeeeeeee 8,8-Meee[‌88‌]

Meeeeeee eee eeeeee eeeeeeeeeeee ee 8,8-eeeee eeee eeeeeeeee ee eeeeeee ee eee eeeeeeee eee ee eeeeee 8,8-eeeeeeee, eeee eeeeeeee eeeeeee eeee eeeeeee eeeeeeeee eeee eeeee eee eeeeeeeeeeee ee eee eeeeeeeee ee eeeeeee eeeeeeeee. Mee eeeeee eeeeeeeeee eeeeeeee eee eeeeee eeeeeeeee eee eeee ee eeeeeeee ee eeeee eeeeeeeeee eeeeee, eeeeeeeeee eeeee eeeeeee eeeeeeeeee eeeeee. Meeeeeee, eeeee eeeeee eeeeeeeeee, 8,8-eeeee eee eeeeeee eeeeeeeeeee eeeeeeeee eeee ee eeeeeeeeeee (eeeeeeeeeee) ee eeeeeeeeeeeee. Meeeeeeeeeee, eeeeeeeee eeeee eeeee eeeeeeeeee eeee eeee eeeeeeeee eeeeeeeeee ee eeeeee eeeeeeeee.

Meeeeeeeeeee Meeeeeeee

8,8,8-Meeeeeeee-8-(8-eeeeeeeeeee)-8,8-eeeeeee [88, M8=(MM8)8Me; M8=M8=M8=Me]; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee 8-eeeeeeeeeee-8-eee [88, M8=(MM8)8Me; M8=Me; 888e, 8eee], 8,8-eeeeeeeeeeeeeee-8,8-eeee (8; 888e, 8.88eee), eee MeMMM8M (8e) ee eeeeeee (888eM) eee eeeeeee eeeee eeeeee eeee eeeeeee ee M8M eeeee e MeeeMeeee eeeeeeeee. Meeee 8.8e, eee eeee eee eeeeee ee ee, eeeeee eeee eee. MeMMM8 eeee (888eM), M8M (8 × 888eM), eee eeeee (888eM), eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee ee eeee eee eeeeeee; eeeee: 888e (88%); ee 88888°M/8.88Meee.

Meeeee 8-(8-Meeeee-8,8-eeeeee-8-ee)eeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeee 8-eeeeeeeeeeeee (88; 8.88e, 88eeee), eeeeeee-8,8-eeee (8; 8.88e, 88eeee), MM(MMe)8 (8.88eM, 88eeee), eee MeMM (88ee) ee eeeee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee ee ee eee 88e. Me8M eee eeeee eee eee eeee eee eeeeee eeee eee. MeMMM8 eeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeee ee eeee eee 8,8-eeeeeee ee ee eee; eeeee: 8.8e (88%); ee 88°M/8.8Meee.

8,8-Meeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eee eeeeeeee eeeeeeee (8.8eee), eeeeeee-8,8-eeee (8; 8.8eee), 8-Å eeeeeeeee eeeeee (88e), eee Meeeeeeee 88 eeeee (8.8e) ee eeeee MMM (88eM) eee eeeeeee ee ee eee 88e. Mee eeeeeee eee eeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eee-eeeeeeee eeeeeeeeeeee ee eeee eee 8,8-eeeeeee ee e eeeeee; eeeee: 8888%.

8,8-Meeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeee eeeeeeeeeee eeeeeeeee (88ee) eee eeeee ee e eeee ee eee eeeeeeee eeeeeeee (8eeee) eee eeeeeee-8,8-eeee (8; 8eeee) ee MM8Me8 (8eM). Mee eeeeeee eee eeeeeee ee eeeeee, eeeeee ee ee, eee eeeeeeee, eee eee eeeeeeee eee eeeeee eeee MM8Me8. Mee eeeeeeee eee eeeeee eeee M8M, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:88) ee eeee eee 8,8-eeeeeee; eeeee: 8888%.

8,8-Meeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me8M+Me8 (8.88eeee) eee eeeee ee e eeeeeee ee eee eeeeeeee eeeeeeee (8eeee), eeeeeee-8,8-eeee (8; 88eeee), eee MM(MMe)8 (8.8eeee). Mee eeeeeee eee eeeeeee ee ee, eeee eeeeee eeee eee. MeMMM8 eeee (88eM), eee eeeeeeeee eeee MeMMe (8 × 88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeee ee ee eeeeeeeeee eeeeeee e eeeee eeeeee ee eeeeee eee; eeeee: 8888%.

8-Meeeee-8,8-eeeeeee (88); Meeeeee Meeeeeeee:[‌88‌,‌88‌]

Meeeee M: MMM (88.8ee, 8.8eeee) eee eeeee ee e eeee ee MeMMM (8.88e, 88eeee), MM(MMe)8 (8.88e, 88eeee), eeeee eee MeMM (888ee, 88eeee), eee eeeee eeeeeee-8,8-eeee (8; 8.88e, 88eeee) ee MM8Me8 (88eM). Mee eeee eee eeeeeee ee ee eee 8e, eee eeee e eeee ee 88% MeMMM8 eeee (88eM) eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (8 × 88eM), eeeee (Me8MM8), eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee 8,8-eeeeeee eeee eeeeee eeeeeeee eeeeee. Meeeeee eeeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeeee; eeeee: 8.88e (88%); ee 888888°M/88Meee.

8,8-M-Meeeeeeeeee-M-eeeeeeeeeeeee (88):[‌88‌]

M eeeeeee ee eeeeeeee M-eeeeeee (88; 88e, 88eeee), MeMe8 (88e, 8.888eee), eee eeeeeee eeeeeeeee MeMMM (888eM, 8.8eee) eee eeeeee ee ee eee 8e, eeeeee ee ee eee eeee, eeeeeee eeee M8M (888eM), eee eeee ee 8°M eee 88eee. Mee eeeeeeeeeee eeeeeeeeeee eee eeeeeeee, eeeeee eeee eeee M8M (8 × 88eM) eee eeee eeee eeeeeee (8 × 88eM), eee eee eeeee ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeeeeeeeee (eeeeeee/MMMe8). Mee eeeeeeeee eeeee eee eeee eeeeeeeee ee eeeeeee M8M (88eM) eeeeeeeeee eeeee ee MM8 (8 eeeee). Mee eeeeeee eee eeeeee eee eee eeee eeee 8eee (eeeeeeeee!) eee eeee eeeeeeee eeeeeee e eeee eeee eee ee eeeeeeeeeeee eeeeee. Mee eeeeeeee eee eeeeeeeeeee eeeeee ee ee eee eeee. Meee eeeeeeeeeeeeeee eee eeeeeeee ee 8°M, eee eeee eeeeeee eee eeeeeeeee ee eeeeeeeeee; eeeee: 8.8e (88%); ee 888888°M; [α]M88 8 (e 8.8, MeMM).

Meeeee 8,8-M-Meeeeeeeeee-M-eeeeeeeeeeeeeee (88):[‌88‌]

M eeeeeeeee eeeeee ee MeMM eee eeeee ee e eeeeeeeeee ee eeeeee M-eeeeeeeeeeeeeee (88; 8.8e, 8.8eeee) ee MeMMM (8.8eM, 88eeee) eee eee eeeeeee eee eeeeeee eee ee ee eee 888e. Me eee eeee eeeeeee eeee MeMMe (88eM) eee eeeeee eeee eee. MeMMM8 eeee (8 × 88eM). Mee eeeeeee eeeee eee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeee eee eeeeeeeeeee eeeeeeeeee ee e eeeee eeeee; eeeee: 8.88e (88%); eeeee ee eeeeeee (α/β) 8:8.

(8M,8M)-8-(Meeeeeeeeeeee)-8-(8-eeeeeeeeeeeee)-8,8-eeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee (8M)-eeeeee-8,8,8-eeeee (88; 88.8e, 888eeee), 8-eeeeeeeeeeeeeeeeeee (88.8eM, 888eeee), eee MMMM (888ee, 8.8eeee) ee eeeeeee (888eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee eeeee eeeeee eeee eeeeeee ee eeeee eeeee e MeeeMeeee eeeeeeeee. Meeee 8e, eee eeeeeee eee eeeeee ee ee, eeeee MeMMM8 (888ee) eee eeeee, eee eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeee e eeeeeee ee eee 8,8-eeeeeee 88 eee eee 8,8-eeeeeeeee 88 (eeeee 88:8) ee e eeeeeeeee eee; eeeee: 88.8e (88%). M eeeeee eeeeeeeeeeeeeee eeeeeeeeeeee eeee eee eeee eeeeeee eeeeee eeee e 88:8 eeeee ee eee eeeeeeee.

References


Cookie-Einstellungen