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Kouklovsky, C., Science of Synthesis, (2007) 29, 503.
The reaction between a 1,3-diol and an acetal (transacetalization) gives 1,3-dioxanes under mild conditions. Transacetalization is catalyzed by protic acids; 4-toluenesulfonic acid, pyridinium 4-toluenesulfonate, camphorsulfonic acid, or acidic resins are the most often used reagents. In contrast to direct acetalization, two molecules of an alcohol are evolved rather than water (Scheme 29).
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee 8,8-Meeee eee Meeeeee ee Meeeee (Meeeeeeeeeeeeeeeee)
Mee eeeeeeeee ee eee eeeeeeeeeeeeeeeeee eeeeeeee ee e eeeeeeee eeeeeee eeeee eeee eeeeeee ee eeeeeeee ee eee eeeeeee eeeeee ee eee 8,8-eeee. Mee eee eeeee eee eeeeeeeeee eee eee eeeeeeeee ee eee eeeeee 8,8-eeeeeee eeeeeeee eeeeeee ee eee eeeeeee. Mee eeeee eeeeeee, eeeeeeee eeeeeee (M8 = Me) eee eeeeeeeee eeeeeeee, eeeee eeeeeee ee eeeeeeee eee ee eeeeeeee ee eeeeeeeeee eeeeeeeeeeee ee ee eee eee ee eeeeeeeee eeeeee. Mee eeeeeeeee eeeeeee eee eeeeee eeee eee eeeeeeeeeeeeeeeeee eee (eeeeeeeeeeeeeee)eeeeeee (88, eeeeeeeeeeee eeeeeeee eeeeee), 8,8-eeeeeeeeeeeeeeee (88, eeeeeee eeeeeeee eeeeee), 8,8-eeeeeeeeeeeeeeeeeeeee (88, eeeeeeeeeeeeee eeeeeeee eeeeee), eee 8,8-eeeeeeeeeeeeeeeeeeee (88, eeeeeeeeeeeee eeeeeeee eeeeee) (Meeeee 88).
Meeeee 88 Meeeeeeee Meeeeeee Meeeeee Meee eee Meeeeeeeeeeeeeeeee Meeeeeeee
Me eeeeeeee ee eee eeeeee eeeeeeeeeeeee eeeeeeee, eee eeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeee eeeee eeee eeeeeeeeee, eee ee eeeeeeeee eeee eeeeeee eee eeeeeeeee ee eeeeeee eeeeeeeeee. Mee eeeeeeee ee eeeee eeeeeee eee ee eeee eeeeeeeeeee, eeee e eeeeeeeee eeeeee ee eeee. Mee eeeeeeeeeeeeeeeeee eeeeeeee ee eee eeee eeeeee eee eee eeeeeeeee ee 8,8-M-eeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeee. Mee eeeeeeeee eeeeeee M-eeeeeee (88), eeeeeeeee (88), ee eeeeeee (88) eeee (eeeeeeeeeeeeeee)eeeeeee (88) eeeee eeeeee eeeeeeeee eeee eeee eeeeee ee eee eeeeeeeeeee eeeeeeeeeee (e.e., 88 eee 88), eeee eeeeee eeeeee eee eeeeeeeeeeee (Meeeee 88).[88–88]
Meeeee 88 Meeeeeeee ee 8,8-M-Meeeeeeeeee Meeeeeeeeee ee Meeeeeeee eeee (Meeeeeeeeeeeeee)eeeeeee[88–88]
Meeeeeeeeeee eeeeee eeeeee eeeeeeeeeee eee eeeeeeeeeee eeee eeeee 8,8-M-eeeeeeeeeee eeeeeee eeeee eee eeee eeeeeeee, eee eeee eeee eeeeee eeeeee. Mee eeeee eeeeeee ee eeeeee eeeeeeeeeeeeee eeeee eeeeeee ee eee eeeeeeeeeeeeeeeee.[88]
Meeeeeee eee eeeeeeeeee eee 8,8-eeeeeee eeeeeeeee eee eeeeee eeee eeeeee eeeeeeeeeeeee, eee eeeeeeeeeeeeeeee eee eeeeee eeeeeeeeee ee eee eeee, eeee eeeeeee eeeeeee eeeeeeee eeeeeeeeeeeeee eeee 8,8-eeeee eeeee eeeeeeeeeeeee eeeeeeeeee. Meeeeeeee, eeeeeeeeeeeeeeeeee eeee 8,8-eeeeeeeeeeeeeeee (88), ee eeee 8,8-M-eeeeeeeeeeeeee eeeeeeeeee 88 ee eeeeeeeeeeee eeee eeeeeeeeeeee 88, eeee ee eeeeeeeee eeeee eeeeeee eeeeeeeeee, ee eeeeeeeee ee eeee eeeeeeeeeee (Meeeee 88).[88] Mee eeee eeeeeeee eeee ee eeeeeeee eeeeeee eeee eee eeeeeeee eeeeeee eeee eeeeeeeeee ee eeeeeeeee ee eee eeeeeeeee ee eeee eeee.
Meeeee 88 Meeeeeeeeeeee ee M-Meeeeee eeee 8,8-Meeeeeeeeeeeeeee eeeee Meeeeee eee Meeeeeeeeeeee Meeeeeeeee[88]
Meeeeee eeeeeee eeeee eeee eee eeee eeeeeeeeeee. Meeee 88 eeeeeeeeee eeee 8,8-eeee eee 8,8-eeee eeeeee eeeee eeeee eeeeeee ee eee 8,8-eeeeeee 88 eee eee 8,8-eeeeeeeee 88 eeee eeeeeee eeee 8,8-eeeeeeeeeeeeeeee (88), eee eeeeeeeee 8,8-eeee eeeeeeeeee eeeeee eeee 8,8-eeeeeeeeeeeeeeee ee eeee (Meeeee 88).[88] Meee eeeeeee eeeee eeeeeee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee ee eeeeee-eeeeeee 8,8-eeeeeeee.
Meeeee 88 8,8-Meee eeeeee 8,8-Meee Meeeeeeeee ee Meeeeeeeeeeeeeeeee[88]
Meeeeeee ee eee eeeeeeee eeeeeee ee eeeeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeee eeee 8,8-eeeee ee e eeeeee eee eeeeeeeee eeeeee eee 8,8-eeeeeee eeeeeeeee. Mee eeeeeeeeeeeee eeeeeeee eeeee eeeeeeee eeeeeeeeeee eee 8,8-eeee eeeeeeeeee eeeeee 8,8-eeeeeeeeee. Mee eeeeeeee ee eee eeeeee 88 eeee (eeeeeeeeeeeeeee)eeeeeee (88) eeeee eeee eeeeeeee 8,8-eeeeeeee eee eeeeee eeeeeeeeeeeeee.[88] Meeee eeee ee eeeeeeeee eeeeeee 8-eeeeeeeeeeeeeee eeee, eeeeeeeeee 8-eeeeeeeeeeeeeeee, ee eeeeeeeeeeeeeee eeee ee eeeeeeeeeeeeeee, eeeeeee, ee eeeeeeeeeeeeeeeee, ee eeee eeeeeeeeeee ee eeee eeeeee eeeeeee. Meeeeeeeeeeee ee eeeeee eeeeeeeeeeeeeee, eee eeeeeeee eeeeeeeeeee ee eee 8,8-eeeeeee eeee eeeee ee eee eeeeeeeeee eeeeeeee. Meee eeeeeeee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeee- ee 8-eeeeeeeeeeeeeeeeeee-eeeeeee eeeeeee ee 8,8-eeeee (e.e., 88 eeee 88) eee eeeeeeeee ee Meeeee 88.[88–88]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee 8,8-Meeee eee Meeeeeeeeeee ee 8-Meeeeeeeeeeeeeeeeee Meeeeeee Meeeeee[88–88]
Meeee eee eeee eeeeeeeeee eee 8,8-eeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeee, eeee eeeeee eee eeee eeeeee eeeeeee ee eee eeeeeeeee ee eeeeeee eeeeeeeee. Me eeeeeeeeee, eee eeeeeeeee ee eeeeeeeeee eeee 8,8-eeeee eee 8,8-eeeeeeeeeeeeeeee (88) eee eeeeee e eeeeeeee eeeeee eee eeeeeee eeeee eeeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee. Mee eeeee eeeeee ee eeeeeeeee eeeeeeeee eeee e 8,8-eeee eee eee eee eeeeeeeeee ee eee M88 eee M88 eeeeeee eeeeee ee eeeeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee eeee e 8,8-Meee ee Meeeeee Meeeeeeeee[88]
Mee eeeeeeee ee eeeeeeeee eeeeeee eee ee eeee eeeeeeeeeee, eeeee eeeeeeeeeeeeeee eeee, 8-eeeeeeeeeeeeeee eeee, eeeeeeeeee 8-eeeeeeeeeeeeeeee, ee eeeeee eeeeee ee eeeeeeeee. Meeeeeeeeeeeeee ee eeeeeee eee eeeeeeeee eeee ee eee eeeeeee. Mee eeeeeeee ee eeeeeeeeeee ee eeeeeee ee eee eeeee ee eeeeee e eeeee eeeeee ee 8,8-eeeeeeeeeeeeeeee, eeeee eee eeee ee eeee ee eee eeeeeee. 8,8-Meeeeeeeeeeeeeee ee ee eeeeeeeeeee, eeeeeeeeeeee eeeeeeeee eeeeeee; ee ee eeeeeeee, eee eee eeeeeeeee ee eeeeee eeeeeee eeee eee eeeeeeee eeeeeee. Meeeeeeeee eee eeeeee ee eeeeee eee eee eee ee eeeeeeee eeeeee ee eeeeeeeeeeeeee. Meee eeeeeee eeeeeeeeee eeeeee eeee ee eeee-eeeeeeeeeeeeeeeeee ee eeee-eeeeeeeeeeeeeeeeee eeeeee eee eeeeee eeeee eee eeeeeeee eeeeeeeeee, eee eeee eeeeeeeeee eeeeee eee eeee eeeeeeeee. Meeeeee, eeee eee eeeeeeeee eeeeeeee e eeee eeeeeee eeeeeee eeeee, e eeeeeee ee eee eeeeee eeeeee eee eeeeeee eeeee eeeeee ee eeeeeeee (e.e., 88 eeee 88). Meeee eeeeee eeeeeeeee eeeeeeeeee eee eeeee eeeeee eeeeeeeeeee, e.e. ee eeee 88 (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee eeee e 8,8-Meee Meeeeee e Meee Meeeeee Meeee [88]
Meee e eeeeeeeeee eeee eee e eeeeeee eeeee eee eeeeeee ee eee eeeeeeee, eeeeeeeeeee eeeeeeeeeeeee eee eeeee eeeeee eee eeeeeeeeeeeee eeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee eeee e 8,8-Meee eeee Meeeeeeeeee Meeeeeeeeeeee[88]
Meeeeee eeeee eeee eeeeeeeee, eeee eeeeee eee 8,8-eeeeeee eeeeeeeee ee eeee eeeeeee ee eeeeeeeee eeeeeeeeee. Meeeeeeeeee eeeeeeeee eeee ee eeeeeeeeeee (eeeeeeeeee ee eeeee-eeee eeeeeeeee) eee eeeeeee. Meeeeeeeee eeee eee- ee eeee-8,8-eeeee eee eeeeeeee ee eeee eeeeee, eeeeeeee eeeeeeee eeee eee-eeeee ee eeeeee. Meeeee ee eeeeee eeeeeeeeeeee ee eee M8 eeeeee eeee eee eeeeeee eee eeeeeeeeeeee eeeeeeee, eee eeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeee eeee eeeeeeeee. Mee eeeeeeeeee eee eeeeee eee eeee eee eeeeeee eeeee eeeeeeeeee eeeeeeeeee e eeeeeeeee, eee eeee eee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeee ee 8,8-eeeee ee MMM eeeeeeee. Meeeeeee eeeeeeee ee 8,8-eeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeee ee eee eeeee eeeeeeeee ee eeeeeee eeeeeeeee, eeeeeeeee 8,8-eeeeeee 88 eee 88 eeee eeeee 88 eee 88, eeeeeeeeeeee, eee eeeeeeeee ee Meeeee 88.[88–88]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee 8,8-Meeee eee 8,8-Meeeeeeeeeeeeeee[88–88]
Meeeeeeeeee ee eeeeeeeee eeeeeeeee eeee 8,8,8-eeeeee ee eeeeeeee ee eeeeeeeeeeeee eeeeeee. eee-8,8-Meeeeeee eee eeee eeeeee eeee eee eeeee-eeeeeee, eee eee eeeeee eeeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee Meeeeeeee ee e 8,8-Meeeeee eeee e 8,8,8-Meeee[88]
Meeeeeeeee eeee ee eeeeeee eeeee eeeeee eeeeeeeee eeee e eeeeeeeeeee eeeeeee eeeee ee eeeeeee. Meee eeeeeeeeeeeee eee eeee ee eeeeeeeee ee eeeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeee eeeeeeeeee. Mee eeeeeee eeeeeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeee. Meeeeeeeeeee, 8,8-eeee-eeeeeeee eee eeeeee eeeeeee ee e 8,8-eee-eeeeee[88] eee eeeeeeee eeeeeeeeee eee eeeeeeeee ee eeeeeeee eeee[88] (Meeeee 88).
Meeeee 88 Meeeeeeeeeeee ee 8,8-Meeeeeee ee Meeeeeeeeeeee 8,8-Meeeeeee[88,88]
Mee eeeee ee eeeeeeeee eee eeeeeeeeee ee eeeeeeeee eeee eeee ee eee eeeeeeeee: 8,8-eeeeeeeee > 8,8-eeeeeeeee > 8,8-eeeeeeeee. Meeeeeeee ee eeeeeee-eeeeeee 8,8-eeeeeee eee eeeeeeeee ee eee eeeeeeeeee 8,8-eeeeeeeee ee e eeee eeeeeee eeeee ee eeeeeee ee eee eeeeeee eeeeee. Meee eeeeeeeeee ee eeee eeeeeeeeee ee eeeeeeeeeeee eeeeeeeee, eeeee 8,8-M-eeeeeeeeeeeeeeeeeeeeeeeeeeeee eee eeeeeeeee ee eee eeee eeeeee 8,8-M-eeeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeee eeeeee eee eeeeeeeeeeeeee. Me eeeeeee ee 8,8-eeeeeee ee 8,8-eeeeeeeee eeeeeeeeeeeee ee eeeee ee Meeeee 88.[88]
Meeeee 88 Meeeeeeeeeeee ee e 8,8-Meeeeee ee e 8,8-Meeeeeeee[88]
Meeeeeee, 8,8-eeeeeeeee 88 (eeeeeeee eeee eeeeeeeee ee eeeeee eeeee 88) eeeeeeeeee ee eee eeee eeeeee 8,8-eeeeeee 88 eeee eeeeee eeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeee ee e 8,8-Meeeeeeee ee e 8,8-Meeeeee[88]
Me eee eeee eeeeee, eeeeeeeeee ee 8,8-eeeee eeee ee 88 eeeeeeeeeeeeee eeeeeee ee eeee eee eeee eeeeee eeeeeeeeeee eeeeeeeeee 88 eeee eeeeeee eeee (eeeeeeeeeeeeeee)eeeeeee (88) eeeee eeeeee eeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeee ee e 8,8-Meeeeeee-8,8-eeeeeee eeee e 8-Meeeee-8,8-eeeeeee[88]
8,8-Meeeeeeeeeeeeeeeeeeee (88) eee 8,8-eeeeeeeeeeeeeeeeeeee (88) eee eeee eeeeeeee eeeeeeee eee eeeeeeeeeeeeeeeeee eeeeeeeee. Meeeeee, eeee eeee eeee eeee eeee eee 8,8-eeee eeeeeeeeee eee eeeeeeee ee 8,8-eeeeeee eeeeeeeee eee eeeeee eeeeeee. Meeeeee, eee eeeeeeeeee ee eee- ee eeee-8,8-eeeee (e.e., 88) ee eeeeeeeeeeeeee ee eeeeeeeeeeeee eeeeeee (e.e., 88) eee ee eeeeee ee eeeeeeeeee eeeeeeeee, ee eeeee ee Meeeee 88.[88,88–88]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee 8,8-Meeee eee 8,8-Meeeeeeeeeeeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeee[88,88–88]
Meeeeee eeeeeeeeeee, eee eeeeeeeeee eeeeeee eeeeeeee eeeeeeeeeee, eee eeeeeeeeeee eeeeeeeeeeeee eee eee eeeeeeeee ee eeeeeee eeeeeee eeeeeeee. Meeee-8,8-eeeeeee eeeeeeee eeeeee ee eeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee. Meeeeeee eeeeeee-eeeeeee 8,8-eeeeeeee eee ee eeeeeeee ee eeeeee eeeeeeeee, eeeeeeeeeeeeeeeeee ee e eeeeee eee eeeeeeeee eeeeee. M eeeeeee eeeeee eee eeeeeeeeeeeeeeeeee ee eeeee-8,8-eeeeeee eeeeeeee eeeeee eeee eeeeeee eeeee, eeeeeeeee 8,8-eeeee, eee eeee eeeeeeeee eeeee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee 8,8-eeeeeeeeeeeeeee.[88] Mee eeeeeeee ee eeeeeeeee, ee eeee eeeeeeeeeee 88 eee eeeeeeee, eee eeeeee eeeeeee eeeeeeeeeeee ee eee eeeeeee eeee eee ee eee 8,8-eeee eeeeee (Meeeee 88).[88–88]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee Meeee-8,8-eeeeeee Meeeeeee Meeeeeeeeee eee 8,8-Meeee[88–88]
| M8 | M8 | M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | M | M | M | 88 | [88] |
| MMe | M | M | M | 88 | [88] |
| M | Me | M | M | 88 | [88] |
| M | M | M | Me | 88 | [88] |
| Me | M | M | Me | 88 | [88] |
| MMe | M | M | Me | 88 | [88] |
| M | MMM | M | Me | 88 | [88] |
| MMM | M | M | Me | 88 | [88] |
| (MM=MM)8 | M | Me | 88 | [88] | |
| M | M | Mee | M | 88e | [88] |
| Me | M | Mee | M | 88e | [88] |
e M 8:8 eeeeeee ee eeee/eee-eeeeeeeeeeeee ee eee eeee.
e M 8:8 eeeeeee ee eeeeeeeeeeeee (eeeeeeeee ee eeeeeeeeeeeeee).
e M 8:8 eeeeeee ee eeeeeeeeeeeee (eeeeeeeee ee eeeeeeeeeeeeee).
Meeeeeee eee eeeeeeeeeeeeeeeeee eeeeeeeee eeee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eeeeee eeeeeee, eeeeeeeeee 8-eeeeeeeeeeeeeeee ee eeee eeee ee eeeeeeee eee eeeeeeee, eeeeeeeeee eee eeeeeeeeeeeeeeeeee eeee eeeeee eeeeeee-8,8-eeee. Mee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeee eee eeeee eeee eeeeee ee eee eeeeee eeeeeee. Meee eeeeeeeee eee eeee eeeeeee ee eee eeeeeeeeeeeeeeeeee ee eeeeeee eeeee-8,8-eeeeeee eeeeeeeeeee, e.e. 88 ee eeee 88 (Meeeee 88).[88–88]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee Meeee-8,8-eeeeeee Meeeeeee Meeeeee Meeee Meeeeeeeee 8-Meeeeeeeeeeeeeee ee e Meeeeeee[88–88]
Meeeeeee eeeeeeeeeeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee eeee eeeeeeee ee eeeeee eeeeeeee eeeeeee, eeeee eeeeeee eee ee eeee ee eeeeee eeeeee eeeeeeeeee. Meeeeee eeeeeeeeee e eeee-8-eeee eeeee ee eee eeeeee eee ee eeeeeeeeeee eeeeeee ee e eeeeeeeeee eee ee eeeeeeeee eeeeeeeeeeeeeee ee eeeeeeeee eeee eeeeee; eeee eeeeeeeeeee eee eeee eeeeeee ee eee eeeeeeeeeeee ee eee eeeeeeee eeeeeeee ee eeeeeeeeeeeee.[88] Me ee eeeeeeeee ee eeee eeeeeeeeeee, eee(eeee-8-eeee) eeeeeee ee eeeeeeeee eee eeeeeee eeee eeee eeeeeeeee eee eee eeeeeeeeeeeee ee 8,8-eeeee ee 8,8-eeeee ee eee eeeeeeee ee M-eeeeeeeeeeeeeeee eee e eeeeeeeee eeeeee ee ee eeee (eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeee).[88] Mee eeeeeeee ee eeee eeeee (8–88 eee) eee eeeeeeee ee eeee eeee-eeeeee eeeeeeeeee eeeeee. Mee eeeeeee ee eee eeeeeeeeeeeee ee e eeeeeeeeeeee-eeeeeeeee eeeeeeeeeeee 88 eeee [eee(eeee-8-eeeeeee)eeeeee]eeeeeee (88) (Meeeee 88).[88] Mee eeeeeeee eeeeeeeeee eeee eee eee eeeeeeeeeeeee eeeeee ee eeeeeeee ee eee eeeeeeeeeeee eeee.
Meeeee 88 Meeeeeeee ee e 8,8-Meeeeee eeee e 8,8-Meee eee [Mee(eeee-8-eeeeeee)eeeeee]eeeeeee[88]
Meeeeeeeee–eeeeee eeeeeeeeeeeeeee ee ee eeeeeeeeeee eeeeee eee 8,8-eeeeeee eeeeeeeee. Mee eeeeeeeeeee eeee 88 ee 8-eeeeee-8,8-eeeeeeeeee (eeeeeeee ee eeeeeeeee ee 8-eeeeee-8,8-eeeeeeeeee eeee 8 eeeeeeeeeee ee eeeeee eeeeeeeeeeeeeeeeeeeeeeeee) eeeeee eeee eeeeeee eeeee, eeeeeeeee 8,8-eeeee, ee eee eeeeeeee ee eeee ee eeee eee eeeeeeeeeeeee 8,8-eeeeeeee (Meeeee 88).[88] Mee eeee eeeeeeeee ee eeee eeeeee ee eeee, ee eeeeeeee ee eeeee eeeeeeeeeeeeeeeeee eeeeeee, ee ee eeeeeeeee eeeee eeeee eeeeeeeeee.
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee eeee 8,8-Meeeeeee-8-eeeeee-8,8-eeeeeeeeeeeeeee Mee(eeeeeeeeeeeeeeeeeeeeeeeee) eee 8,8-Meeee[88]
| M8 | M8 | M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | M | M | M | 88 | [88] |
| Me | M | M | M | 88e | [88] |
| Me | M | M | Me | 88e | [88] |
| M | M | Me | M | 88 | [88] |
| Me | Me | M | Me | 88e | [88] |
e Meeeeee ee eeeeeeeeeeeee.
Meeeeeeeeeee Meeeeeeee
8,8-M-Meeeeeeeeee-M-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
M-Meeeeee eee eeeeeeee ee 88°M/8.8 Meee eee 8 e. M eeeeeee ee M-eeeeeee (88; 88.8 e, 88 eeee), MeMM(MMe)8 (88; 8.8 e, 88 eeee), eee MeMM (88 ee) ee eeeee MMM (88 eM) eee eeeeeee ee 88°M ee e eeeee eeeeeeeee ee e eeeee eeee (eeeeeeee eeeeeeee 888 Meee). M8 eee eeeeeee eeee eee eeeee ee eeeee ee eeeeee MeMM. Meeee 88 eee, eee eeee eeeeee eeeee. Me eee eeeeee ee ee eee Me8M (8.8 eM) eee eeeee. Mee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eeeeeee eeeee. Meee eee eeeeeeeeeee ee eeeeeee (88 eM), eeeeee eee (88 e) eee eeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/MeMMe 8.8:88.8) ee eeee eee eeeeeeeeeee eeeeeeeeee ee ee eeeeeeeee eeeee; eeeee: 88.8 e (88%); Me 8.88 (MeMMe); ee eeeee ee eeeeeeeeeeeeee (M8M/MM8);[88] ee 888–888°M.
8,8-M-Meeeeeeeeeeeee-M-eeeeeeeeeeeee (88):[88]
Me e eeeeeee eeee ee M-eeeeeee (88; 8.8 e, 88.8 eeee) ee MMM (88 eM) eeee eeeee MeMM•M8M (88 ee) eee 8,8-eeeeeeeeeeeeeeee (88; 8 eM, 88 eeee). Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeee eeee Meeeeeeee MMM-888 (MM− eeee). Me eee eeeeeeeee ee eeeeee eeee eeeeeee ee eee eeee eee eeeeeeee. Mee eeeee eee eeeeeeee eee eee eeeeee eeee MeMM. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee 88°M eee eee eeeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMM/MMMe8 8:888, 8:88, 8:88, eeee 8:88). Meeeeee eeee MeMM/MMMe8 (8:88) eeeeeee 8,8:8,8-ee-M-eeeeeeeeeeeeee-M-eeeeeeeeeeeee (88 ee). Meeeeee eeee MeMM/MMMe8 (8:88) eeee eee eeeeeee eeeeeee ee eeeee eeeeeeee; eeeee: 8.8 e (88%); eeeeeeee eeee e eeeee eeeeee ee 8,8-M-eeeeeeeeeeeeee-M-eeeeeeeeeeeee (888 ee). Mee eeeeeee eeeee ee eeeeeeeeeeeeee (MeMM/Me8M) ee eeee eeeeeeeee eeeeeee: ee 888°M; [α]M88 −8.8 (e 8, M8M).
(8M,8M,8M)-8-(Meeeeeeeeeeeeee)-8-[(eeee-eeeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeee (88); Meeeeee Meeeeeeee:[88]
MeMM(MMe)8 (88; 8 eM) eee MMMM (8.8 e, 8.88 eeee) eeee eeeee ee e eeee ee 8-(eeeeeeeee)-8-(eeee-eeeeeeeeeeeeeeeeeee)eeeeeee-8,8-eeee (88; 888 ee, 8.88 eeee) ee MMM (88 eM). Mee eeee eee eeeeeee ee ee eee 88 e eee eeee eeeeeee eeee MeMMe. Mee eeee eee eeeeee eeee eee. MeMMM8 eee eeeee, eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeee 8:88) ee eeee eee 8,8-eeeeeee ee ee eee; eeeee: 888 ee (88%).
(8M,8M)-8-Meeeeee-8-[(8M,8M,8M)-8,8,8-eeeeeeeee-8-{(8M)-8-[(8M,8M)-8,8,8-eeeeeeeee-8,8-eeeeee-8-ee]eeeee}-8,8-eeeeee-8-ee]eeeee-8-ee (88):[88]
M eeee ee 8-eeeeeee-8,8,8,8-eeeeeeeeeeeeeeeee-8,8,8,8,88-eeeeee (88; 88 ee, 8.888 eeee) eee MMM (8 ee) ee 8,8-eeeeeeeeeeeeeeee (88; 8 eM) eee eeeeeee ee ee eeeeeeeee. Mee eeee eee eeee eeeeee eeee ee MeMMM8 eee eeeeeeeee eeee Me8M. 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 eeeee eeeeee 88 ee e eeeeeeeee eeeee eeee eeeeeeeeeeee ee eeeeeeee; eeeee: 88.8 ee (88%).
M eeee ee eee eeeeee 88 (8.8 ee, 8.88 eeee) eee eeeeeeeee ee MeMM (8 eM), eee 8 M MeMM eeee (8.8 eM) eee eeeee. Meeeeee (8 eM) eee eeeee eee eee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meee eeeeeeeee eee eeeeeeee eeeeeee eeeee. Mee eeee eee-8,8-eeeeeee eee eeeeeeee ee e eeeeeeeee eeeee; eeeee: 8.8 ee (88%).
(8M,8M,8M,8M,8M)-8-(eeee-Meeeeeeeeeeeeeeeeee)-8,8-(eeeeeeeeeeeeeeeeeee)-8-[(8-eeeeeeeeeeeee)eee]-8,8,8-eeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
M eeee ee (8M,8M,8M,8M,8M)-8-(eeee-eeeeeeeeeeeeeeeeeee)-8-(8-eeeeeeeeeeeeeeee)-8,8,8-eeeeeeeeeeeeeeee-8,8-eeee (88; 88 ee, 8.888 eeee) ee 8,8-eeeeeeeeeeeeeeee (88; 8.8 eM) eeeeeeeeee e eeeeeeeee eeeeee ee MMMM eee eeeeeee ee ee eeeeeeeee. M8M (8 eM) eee eeeee eee eee eeee eee eeeeeeeee eeee Me8M (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeee 8:8) ee eeee eee eeeeeeeee eeeeeee; eeeee: 88.8 ee (88%); eeeeeeee eeee eeee eeeeeeee eeeeeeee (8 ee).
Meeee (8M,8M,8M,8M,8M)-8-(eeee-Meeeeeeeeeeeeeeeeee)-8,8-(eeeeeeeeeeeeeeeeeee)-8,8,8,8-eeeeeeeeeeeeee-8-eeeeee (88); Meeeeee Meeeeeeee:[88]
8,8-Meeeeeeeeeeeeeee (88; 8.88 eM, 8 eeee) eee MMM (88 ee, 8.8 eeee) eeee eeeeeeeeeeee eeeee ee e eeee ee eeeee (8M,8M,8M,8M,8M)-8-(eeee-eeeeeeeeeeeeeeeeeee)-8,8-eeeeeeeee-8,8,8,8-eeeeeeeeeeeeee-8-eeeeee (88; 888 ee, 8 eeee) ee eeeee eeeeeee (8 eM). Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 eee eee eeee Me8M (8.88 eM, 8.88 eeee) eee eeeee. Mee eeeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeee ee Me8M. Mee eeee eee eeeeee eeee M8M, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:88) ee eeee eee 8,8-eeeeeee ee e eeeeeeeee eee; eeeee: 888 ee (88%).
(8M)-8-[(8M,8M)-8,8,8-eeeeeeeee-8,8-eeeeee-8-ee]eeeee-8-ee (88):[88]
88% Me/M (888 ee) eee eeeee ee e eeee ee 8-[8-(eeeeeeeee)-8-eeeeeeeeeee]-8,8,8-eeeeeeeee-8,8-eeeeeeeee (88; 8.8 e, 88.8 eeee) ee MeMM. Mee eeeeeeeeee eee eeeeee eeeee e M8 eeeeeeeeee eee eeeeeee ee ee eee 88 e. Mee eeeeeee eee eeeeeeee eeeeeee e eee ee Meeeee eeee eee eeeeee eeee MM8Me8. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeee eeeeeee eee eeeeeeeeeee ee eeeeeee (888 eM). Meeee MeMM8 (8 e) eee MMM (88 ee) eeee eeeeeeeeeeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e, eeee eeeeee eeee M8M (88 eM), eee. MeMMM8 eeee (88 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeeeee eeeee 8:8) ee eeee eee 8,8-eeeeeee ee e eeeeeeeee eee; eeeee: 8.88 e (88% eeee eee eeeee).
(M)-8-Meeeee-8,8-M-eeeeeeeeeeeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[88]
8,8-Meeeeeeeeeeeeeeeeeee (88; 8.88 eM, 88 eeee) eee MeMM•M8M (888 ee, 8.88 eeee) eeee eeeee ee e eeee ee (8M)-8-eeeeeeeeee-8-eee-8,8-eeee (88; 888 ee, 8.8 eeee) ee MM8Me8. Mee eeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeeee ee eeeeeeee ee eee. MeMMM8 eeee. Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:88) ee eeee eee 8,8-eeeeeee ee e eeeeeeeee eee; eeeee: 888 ee (88%).
8,8-Meeeeeee-8,8-eeeeeeeeee[8.8]eeeeee-8,88-eeee-8-eee (88, M8 = M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[88]
M eeee ee 8,8-eeeeeeeeeeeeeeeeee-8,8-eeee-8-eee (888 ee, 8 eeee) eee 8,8-eeeeeeeeeeeeeee-8,8-eeee (888 ee, 8 eeee) ee MMM (88 eM) eee eeeeeee ee ee eee e 8 M eeee ee MM8•MMe8 ee MMM (8.88 eM, 8.88 eeee) eee eeeee eeee 88 eee. Mee eeeeeee eee eeeeeee ee ee eee 88 eee eee eeee eeeeeee eeee Me8M (88 eM). Mee eeee eee eeeeee eeee eee. MeMMM8 eeee (88 eM) eee eeeee (88 eM), eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeee/Me8M 8:88:8) ee eeee eee 8,8-eeeeeee ee e eeeeeeeee eeeee; eeeee: 888 ee (88%); ee 888–888°M.
8-Meeee-8-[(eeee-eeeeeeeeeeeeeeeeeee)eeeeee]-88-(eeee-8-eeee)-8,8-eeeeeeeeee[8.8]-8,88-eeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[88]
M eeee ee 8-eeeee-8-[(eeee-eeeeeeeeeeeeeeeeeee)eeeeee]-8,8-eeeeeeeee-8-(eeee-8-eeee)eeeeeeeee-8,8-eeee-8-eee (88; 8.8 e, 8.88 eeee), eeeeeee-8,8-eeee (8; 8.8 eM, 8.88 eeee), eee MMMM (88 ee, 8.88 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee eeeee eeeeee eee 88 eee. Meeee eeeeeee ee ee, eM 8 eeeeee eeee eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:88) ee eeee eee 8,8-eeeeeee ee e eeeee eeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
| [47] | Meeeeeee, M. M., Me., Me Meeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeee, M. M.; Meeeeee, M. M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
| [55] | Meeeee, M. M.; Meeee, M.; Meeeeeee, M.; Meee, M.; M'Meeeee, M.; Meeeeeeeeee, M., Meeeeeeee. Mee., (8888) 888, 88. |
| [56] | Meeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meeee, M. M., Meee. M. Meee., (8888) 88, 88. |
| [57] | Meeeeee, M.; Meeeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |
| [58] | Meeee, M. M., Meeeeeeee. Mee., (8888) 88, 888. |
| [59] | Meee, M.; Meeeeeee, M., Meeeeeeee. Mee., (8888) 88, 88. |
| [60] | Meeeeeee, M. M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [61] | Meeeöeeee, M.; Meeeee, M., Mee. Meee., (8888) 8, 8888. |
| [62] | Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeeeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 88888. |
| [63] | Meeee, M. M.; Mee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 888. |
| [64] | Meeeee, M.-M.; Meeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee.–Mee. M., (8888) 88, 8888. |
| [65] | Meeeeeeeeee, M.; Meeeeee, M. M., Mee. Meeeee. Meee., (8888) 8, 888. |
| [66] | Meeee, M. M., MM; Meeeeeeee, M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [67] | Meeeee, M.; Meee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [68] | Meeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
| [69] | Meeeeeeee, M.; Meeeee, M.-M.; Meeeeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [70] | Meeeeee, M. M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [71] | Meeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [72] | Meeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [73] | Meeee, M. M.; Meee, M. M.; Meee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [74] | Meeee, M. M.; Me, M.; Meeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [75] | Meeeeee, M.-e.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [76] | Meeeeeee, M.; Meeeeeee, M.; Meee, M.; Meeee, M.; Meeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [77] | Meeeeeee, M. M.; Meee, M.; MeMeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [78] | Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [79] | Meeee, M.; Meeeee-Meeeeeee, M.; Meeee, M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [80] | Meeeeeee, M.; Meeeeee, M. M.; Meeeee, M.; Meee, M.; Meeee, M. M.; Meeeeeee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [81] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., Meee. Meee. Meee, (8888) 88, 888. |
| [82] | Meeeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [83] | Míee-Meeeee, M.; Meeeeee, M. M.; Mee, M. M.; Meeeeeeee, M.; Meeéeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [84] | Meeeeeeeeee, M. M.; Meeeeeeee, M. M.; Meee, M.; Meee, M., Meeeeee, (8888), 888. |
| [85] | Meeee, M.; Meeeeeee, M.; Mee, M. M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [86] | Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [87] | Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [88] | Meee, M.; Meeeeeee, M.; Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [89] | Meeeeee, M. M.; Meee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [90] | Mee, M.; Meeeeee, M. M.; Meeee, M. M., Me., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [91] | Meeeeeee, M.; Meeee, M. M., Mee. Meee., (8888) 8, 8888. |
| [92] | Me, M.; Meee, M. M.; Meeee, M.-M.; Meeeeeeee, M.; Meeeeee, M. M.; Meeee, M. M., Me., M. Me. Meee. Mee., (8888) 888, 88888. |
| [93] | Me, M.; Meeeeee, M. M.; Meeee, M. M., Me., M. Me. Meee. Mee., (8888) 888, 8888. |
| [94] | Me, M.; Me, M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeeeeee, M.; Meeeeeeeee, M. M.; Meeee, M. M., Me., Mee. Meee., (8888) 8, 8888. |
| [95] | Meeee, M. M.; Me, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [96] | Meeeee-Meee, M.; Meeeeee, M. M.; Me, M.; Meeeeeee, M.; Meeeeee, M. M.; Mee, M. M.; Meeeeee, M.; Meeeee, M., Meeeeee, (8888), 888. |
| [97] | Meeeee, M.; Meeeee-Meee, M., M. Mee. Meee., (8888) 88, 888. |
| [98] | Meeeeee, M. M.; Meeeeeeee, M.; Meeeee-Meee, M., M. Mee. Meee., (8888) 88, 8888. |
| [99] | Meeeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 88.
- 8.Meeeee-Meee, (8888) M 88e8, 88.
- 8.Meeeee-Meee, (8888) M 88e8, 88.
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