You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via43.8.2.5.1 Method 1: Alkyne Metathesis
Please login to access the full content or check if you have access via
Krueger, A., Science of Synthesis, (2008) 43, 516.
Alkene metathesis is a widely used method to prepare even highly functionalized alkenes using various types of transition metal catalysts.[193] Although known for about the same period of time, alkyne metathesis (Scheme 61) has not found equivalent application in synthetic chemistry so far owing to the originally required harsh conditions, low functional group compatibility, and sensitive catalysts.[193–195] Nevertheless, it is a useful and versatile tool for the preparation of alkynes and has found wider attention for the synthesis of complex natural products.[196,197] One of the main applications is the production of macrocyclic alkenes with defined E/Z structures after selective hydrogenation with either Lindlar's catalyst or ruthenium-catalyzed hydrosilylation–protodesilylation.[196–200] The preparation of complex structures involving alkynes, e.g. macrocyclic compounds, oligomers, and unsymmetrical alkynes, has also advanced to a reproducible, easily manageable reaction method.[201,202] This section will discuss the different catalysts that are available today, their scope and limitations, and the preparative use of homodimerization and cross-metathesis reactions for the synthesis of linear alkynes from alkynic precursors.
Meeeee 88 Meeeeee Meeeeeee eee Meeeeeeee ee Meeee-Meeeeeeee Meeeee Meeeeeeeee[888,888]
Mee eeeee eeeeeee ee eeeeee eeeeeeeeee eee eeeeeeee ee eeeee ee 8888.[888] Me eeeee eeeeeeeeeee e eeeeeeeeeeeee eeeeeeee eeeee ee eeeeeeee(MM) eeeee eee eeeeee eee eee eeee. Me eeeeeeee eeeeee eeee eeeeeeeeeeee (888–888°M) eee eeee eee eee eeeeeeee eee eee eeeeeeeeeeeeee ee eeeeee, eeeeee eeeeeeeeeeeeee eeeeeeeee. Mee eeeeeeeee ee eee eeeeee eeeeeeeeee eee eeeeeeeee ee 8888 (eee Meeeee 88).[888] Meeee eeeeeeeeeeeeee eeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeee eeeeeee ee eee eeeeeeeeee eeeeeee.[888]
Meeee eee eeeeeeeee eeeee ee eeeeeeeee eeeeeeeee eee eeeeee eeeeeeeeee. Meeee eeeeeee eeeeeeeeeeeee eeeeeee, eeeeee ee eeeeeeee ee eeeee eeeeee eeee eeeeee eee[888] ee ee eeeeeeeeeee eeeee eeeeeeeee ee eeeeee eee (Meeeee 88).[888,888] Meeee eeeeeeeee eee eeeeee eeeeeeeee eeee eee eeeeeeee eeeeeee, eee eeeeeee eeee eeeeeeeeeeee ee eeee eeeee.[888] Meeee eeeeeeeeee eeeee eeeeeeeee eee eee eeee eeeee eeeeeeeeeee, eee ee eeeeeee eeee eee eeeeee eeeeee, eeeeee eeeeeee, eee eee ee eeeeeeee.
Meeeee 88 Meeeee Meeeeeeeee Meeeeeeee Meeeeeeeeee ee Meeeee Mee[888,888]
Meeeeeeeeeeeeeeeeeeeee(8) eee eeee eeeeeeee ee eeeeeee eeeeeeee eeeeee eeee eeee eeeeeeee eeee e eeeeeeee eeeeeeee, e.e. eeeeee ee eeeeeeeeee, eeeee eeeeeeeee eee eeeeeeee.[888–888] Mee eeeeee eeeeeee eeeeeeee eeeeee eeee eeeeeeeeeeee eee eeee eee eeeeeeee eeeeeeeeee eeeeee eeee ee eeeeee, eeeeeeeee, ee eeeeeeeee. Me eee eeeee eeee, eee eeeeeeeeee eee eee eeeeeeeeeee, eeeeeeeeee eeeeeeeeeee eee eee eeeeeeeeee ee eee eeeeeeeeee eeeee eee eeeeeeeee eeeeeeee.[888,888] Mee eeeeeeeee eeeeeeee ee eeee ee eee eeeeeeeee eeeeeeee eeeeeeeeee eee ee eeeeeeee ee eeeeeee ee eee eeeeeeee eeeeee eeeeeeeee (eeeeee eee-8-eee),[888] eee eee ee eeeeeeeee eeeeeee,[888] ee eee eeeeeeeeeee eee ee eee-8-eee eee eeeeeeee eeeeeeeeee.[888] Meeeeeeee eeeeeeee eee eee eeeeeeee ee 8,8-eeeeeeeeeeeeee ee eeeeeeeeeeeeeee, eeeee eeeeeeeeeeeee eeeeeee eee eeeeeeeee eeeeeeee.[888,888,888] Meeee, e eeeeeeee eeeeeeee eeeee ee eeeeeeeeeeeeeeeeeeeeee(8) eee 8-eeeeeeeeeeee eee eeeeeeeee, eeeee ee eeeeeeee eee e eeeee eeeee eeeeeee ee eeeeeeeeee eeeeeeeeee eeeeee (eee Meeee 8) eee eeeeeeee eeeee eeeeeeeeeeee eeee eee eeeeeeee eeeeee.[888,888,888,888] Meeee eeeeeeee eeeeeeeeee eeeeeee 8-eeeeeeeeeeee eee 8-eeeeeeeeeeee.[888,888] Me eee eeee eeeeeeeeee eeee eeeeeee eeeeeeee eeee eee eeee eeeeeeee eeeeee eeeeeee eeeeee eeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeee(8) eeeeeee eeeeeeee ee e eeeeee eeeeeeeee (8-eeeeeee eeeeee eeee ee eeeeeeeeeeeee).[888] Meeeeee eeeeeeeeeeee ee eee eeeeeeee eeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeee ee eee eeeeeeeeee eeeeeee [eeeeee MeM8(eeee)8] eee eee eeeeeeee eeeeeeeee, eeeeeeeee ee eeeeeeee eeeeeeeeee ee eeeee eeeeeeeeeeee eee eeeeee eeeeeeeeeee.[888,888] Me eee ee ee eeeeeeeee eeee eeeeeeee eeeeeee ee eee eeeeeee eeeeeeeeee eeee eeeee eeeeeeeee; eeeeeee eeee eeee eeeeeeeeeeeeeeeeee eeeeeeee.[888,888,888,888]
M eee eeeeeeeeee-eeeee eeeeeeee 888 eeeeeeeee eeeee eeeee eeeeeee eeee eeee-eeeee eee eeee eeeeee (Meeeee 88).[888] Meeee eeeeeeee ee ee eeeeeeeee eeee ee eeeeeeeeeeeeeee eeee eeeeeeee eeeeeeeeeee eeeeeeeee eee eeeeee eeeeeeeeee ee eeee eeeeeeeeeee eee eeeee e eeee eeeeeeeeeeeee eeee eeeeeeeeee eeeeee (Meeee 8).[888–888] Me eeeeeeeee eee eeee eeee ee e eeeeeee ee eeeeeee eeeeeee eeeeeeeee (eee Meeee 88 eee eeeeeeee).[888–888]
Meeeee 88 Meeeeeeee ee Meeeeeeeeee Meeeee Meeeeeeeee Meeeeeeee[888]
Meeee 8 Meeeeeeeee Meeee Meeeeeeeeeeee ee Meeeeeeee eee Meeeee Meeeeeeeee[888–888]
| Meeeeeeeee Meeeee | Me(MM)8 + Me8MMe | Me(MM)8 + 8-MeM8M8MM | Me(MM)8 + Me8Me + Me8MM | (e-MeM)8M≡Me-Me | Me[M(e-Me)Me8]8 + MM8Me8 |
|---|---|---|---|---|---|
| eeeeee | + | + | |||
| eeeeeeee | − | − | + | + | |
| eeeeee | + | + | + | + | + |
| eeeee | + | + | + | + | + |
| eeeee eeeeeee | + | ||||
| eeeee eeeeeeee | + | + | + | ||
| eeeee (eeee eeeeee) | + | − | |||
| eeeeeeee eeeee | + | + | |||
| eeee | + | + | + | + | |
| eeeeee | + | + | |||
| eeeee | +e | − | + | + | |
| eeeee | + | ||||
| eeeeeeeee | + | ||||
| eeeeee | + | + | |||
| eeeeeee | −/+ | + | + | ||
| eeeee | − | + | + | ||
| eeeeeeeee | − | + | |||
| eeeeeeee | − | − | − | + | |
| eeeee (M-eeeee) | − | − | − | − | + |
| eeeee eeeee | − | − | − | + | + |
| eeeeeee | − | − | − | + | |
| eeeeeeeeeee | + | + | |||
| eeeeeee | − | − | + | + | |
| eeeeeeee | − | − | + | ||
| eeeeeeeeeeeee | − | − | −/+ | + | |
| eeeeeeeee | − | − | − | + | |
| eeeeeeeee | − | − | − | + | |
| eeeeeeee | − | − | + | + |
e + = eeeeeeeeee, – = eee eeeeeeeee; −/+ = eeeeeeeee ee eeee eeeee.
e Me eeee eeeee Me8 = Me, eeeeeeee eeeeeee eeeeeee eeeee eeeeeeeeeee eeeeeee eee eeeeeeee.
e Me eeeee ee e eeeeee eeee, ee eeeeeeeeee ee eeeeeeee.[888]
Me eeeeeeee ee eeeeeeeeee-eeeee eeeeeeeee, eeeeeeee eeeeeeeee eee eee ee eeeeeeeee eeeeee eeeeeeeeee eeeeeeeee. Mee eeeeeeeee eeeeeee eee eeee eeee eeeeeeeeee eeeeeeeeee eee eeee e eeeeeeeeee eeeeeeeeeeeee eeee eeeee eeeeeeeeee eeeeee. Meeeeee, eee eeeeeee (e-MeM)8M≡Me-Me (888, M8 = e-Me) ee eeee (eee Meeeee 88).[888,888] Me eeeee eeeeeeeee eeeeeeee eeee ee eeee eeeeeeeeeee eee ee eeeeee eeee eeeeeee eeee eeeeeeeeeee eee 88°M. Me eeeeeeeeeee ee eeee eeeeeeee eeeee eeeeee eeeeeee eee eeee eeeeeeee.[888] Me eeee eeeeeee eee eeeeeeeeee ee eeeeeeee eeeeeee ee eeee eeeeee (eee Meeee 88).
M eeeeeee eeeeeeee eeee e eeeeeeee eeeeee eee eeee eeeeeeee.[888] Mee [(8,8-eeeeeee-8M-eeeeeeee-8-eeeeeee)eeeee)(eeeeeeeeee)eeeeeeee eeeeeee 888 eeeeeeeee eee eeeee-eeeeeeeeee eeeeeeee ee 8-eeeeeeeeeeeeee ee eeee eeeeeeeeeee (eee Meeeee 88). Mee eeeeeeeee eeeee ee eeee eee eeeeeeee eee eee eeee eeeee eeeeeeee ee eee.
Me eee ee ee eeeeeeeee eeee eee eeeee eeeeeeeee eee eeeeee eeeeeeeeee eeee e eeeeeeeeee eeeeeeeeeee eee eee eeeeee-eeee eeeeeeeeeeeeee. Me eeeeeeee ee eeeeeeee eeee eeeeeee eeee eee eeeeeee ee eee eeeeeeee (eee Meeee 88).[888–888] Meeee 88 eeeee eeeeeeee ee eeeeeee 888 eeeeeeeeeee ee eeeee-eeeeeeeee eeeeee eeeeeeeeee.[888,888,888,888,888,888,888–888,888,888,888–888,888–888]
Meeee 88 Meeeeee ee Meeee-Meeeeeeee Meeeee Meeeeeeeee[888,888,888,888,888,888,888–888,888,888,888–888,888–888]
| M8 | M8 | M8 | M8 | Meeeeeeee | Meeeeeeeee | Meeee (%) ee 888 | Mee |
|---|---|---|---|---|---|---|---|
| Me | Me | Me | Me | MM8 ee eeeeee eee eeeeeeeeee ee 888°M | 888–888°M eeee eeeeeee, 88 eee |
88 | [888] |
| Me | Me | Me | Me | MeM≡Me[M(e-Me)Me8]8 ee eeeeee eee | ee, eeeeeee eeeeeeee | 88 | [888] |
| Me | Me | Me | Me | e-MeM≡Me(MM8e-Me)8=MMe-Me ee eeeeee eee | ee, 88 eee | –e | [888] |
| 8-Mee | Me | 8-Mee | Me | Me(MM)8, eeeeeeeeee | eeeeee eeee, Meeeeee, 888°M, 8 e | 88.8e | [888] |
| Me | Me | Me | Me | Me(MM)8, MeMM | 88 e, eeeeee, 88°M | 88 | [888] |
| Me | Me | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeee, 88°M, 8 e | 88 | [888] |
| Me | Me | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeee, 88°M, 8 e | 88 | [888] |
| Me | (MM8)8MMe | Me | (MM8)8M8Me | Me(MM)8, 8-MeM8M8MM | eeeeee, eeeeee, 8 e | 88 | [888] |
| Me | (MM8)8Me | Me | (MM8)8Me | Me(MM)8, 8-MeM8M8MM | eeeeee, eeeeee, 88 e | 88 | [888] |
| Me | (MM8)8MM8Me | Me | (MM8)8MM8Me | Me(MM)8, 8-MeM8M8MM | eeeeee, eeeeee, 88 e | 88 | [888] |
| Me | (MM8)8MM | Me | (MM8)8MM8 | Me(MM)8, 8-MeM8M8MM | eeeeee, eeeeee, 88 e | 88 | [888] |
| Me | Me | Me | Me | Me(MM)8, 8-MeM8M8MM, 8,8-eeeeeeeeeeeeeee | MeMe, 8-Å eeeeeeeee eeeeee, 88°M, 88 e | 88 | [888] |
| Me | Me | Me | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 88 eee | 88 | [888] |
| 8-MeMM8M8 | Me | 8-MeMM8M8 | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 8 e | 88e | [888] |
| 8-MeMM8M8 | Me | 8-MeMM8M8 | Me | Me(MM)8, 8-MM8M8MM, eee-8-eee | MeMe, eeeeee, 8 e | 88e | [888] |
| 8-MeM8M8 | Me | 8-MeM8M8 | Me | Me(MM)8, 8-MM8M8MM, eee-8-eee | MeMe, eeeeee, 88 eee | 88 | [888] |
| (MM8)8MMMMMM | Me | (MM8)8MMMMMM | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 8 e | 88e | [888] |
| (MM8)8Me | Me | (MM8)8Me | Me | Me(MM)8, 8-MM8M8MM, eee-8-eee, 8,8-eeeeeeeeeeeeeee | MeMe, eeeeee, 8 e | 88 | [888] |
| Me | Me | Me | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 8 e | 88 | [888] |
| 8-M8MM8M8 | Me | Me | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 88 eee | 88 | [888] |
| 8-MeMM8M8 | Me | Me | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 88 eee | 88 | [888] |
| 8-MeM8M8 | Me | Me | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 8 e | 88 | [888] |
| (MM8)8MM8Me | Me | Me | Me | Me(MM)8, 8-MM8M8MM | MeMe, eeeeee, 8 e | 88e | [888] |
| Me | MMM | Me | Me | Me(MM)8, 8-MM8M8MM, eee-8-eee | MeMe, eeeeee, 8 e | 88e | [888] |
| (MM8)8MMe | Me | (MM8)8MMe | Me | Me(MM)8, 8-MeM8M8MM | eeeeee, 8 e | 88 | [888] |
| (MM8)8MMe | (MM8)8MMe | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeeeeeeeeeeeee (8 eeeee), eeeeeee, eeeeee, 88 e | 88 | [888] |
| (MM8)8MMe | (MM8)8MMe | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeeeeeeeeeeeee (88 eeeee), eeeeeee, eeeeee, 88 e | 88 | [888] |
| (MM8)8MMe | (MM8)8MMe | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeeeeeeeeeeeee (8 eeeee), eeeeeee, eeeeee, 88 e | 88 | [888] |
| (MM8)8MMe | (MM8)8MMe | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeeeeeeeeeeeee (88 eeeee), eeeeeee, eeeeee, 88 e | 88 | [888] |
| (MM8)8MMMM | (MM8)8MMMM | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeeeeeeeeeeeee (8 eeeee), eeeeeee, eeeeee, 88 e | 88 | [888] |
| (MM8)8MMMM | (MM8)8MMMM | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeeeeeeeeeeeee (88 eeeee), eeeeeee, eeeeee, 88 e | 88 | [888] |
| (MM8)8MMe | Me | Me | Me | Me(MM)8, 8-MeM8M8MM | eeeeeee, eeeeee, 88 e | 88 | [888] |
| 8-MMM8M8 | Me | 8-MMM8M8 | Me | Me(MM)8 | eeeeeee, eeeeee | 88 | [888] |
| 8-MMM8M8 | Me | 8-MMM8M8 | Me | Me(MM)8 | eeeeeee, eeeeee | 88 | [888] |
| 8-MMM8M8 | (MM8)8Me | 8-MMM8M8 | (MM8)8Me | Me(MM)8 | eeeeeee, eeeeee | 88 | [888] |
| 8-Mee | Me | 8-Mee | Me | Me(MM)8, 8-MeM8M8MM | 8,8-eeeeeeeeeeeeeee, 888°M, 88–88 e | 88 | [888] |
| 8-Mee | Me | 8-Mee | Me | Me(MM)8, 8-MeM8M8MM | 8,8-eeeeeeeeeeeeeee, 888°M, 88–88 e | 88 | [888] |
| 8-Mee | Me | 8-Mee | Me | Me(MM)8, 8-MeM8M8MM | 8,8-eeeeeeeeeeeeeee, 888°M, 88–88 e | 88 | [888] |
| 8-eeeeeeee | Me | 8-eeeeeeee | Me | Me(MM)8, 8-MeM8M8MM | 8,8-eeeeeeeeeeeeeee, 888°M, 88–88 e | 88 | [888] |
| 8-MeM8M8 | Me | 8-MeM8M8 | Me | Me(MM)8, 8-MeM8M8MM | 8,8-eeeeeeeeeeeeeee, 888°M, 88–88 e | 88 | [888] |
| 8-M8MM8M8 | Me | 8-M8MM8M8 | Me | Me(MM)8, 8-MeM8M8MM | 8,8-eeeeeeeeeeeeeee, 888°M, 88–88 e | 88 | [888] |
| 8-MeMM8M8 | Me | 8-MeMM8M8 | Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 8 e | 88 | [888] |
 |
Me | |
Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 88 e | 88 | [888] |
| e-Me | MMM | e-Me | MMM | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 88 e | 88 | [888] |
| |
Me | |
Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeee, 88°M, 88 e | 88 | [888] |
| |
Me | |
Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 88 e | 88 | [888,888] |
| |
Me | |
Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 88 e | 88 | [888,888] |
| |
Me | |
Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 88 e | 88 | [888] |
| |
Me | |
Me | Me(MM)8, 8-MeM8M8MM, eeeeee eee-8-eeee | 8,8-eeeeeeeeeeeeeee, 888°M, 8 e | 88 | [888,888] |
| 8-M8MM8M8 | Me | 8-M8MM8M8 | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MMMM8M8 | Me | 8-MMMM8M8 | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MMM8M8 | Me | 8-MMM8M8 | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MeMM8M8 | Me | 8-MeMM8M8 | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MeM8MM8M8 | Me | 8-MeM8MM8M8 | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-M8MM8M8 | Me | (MM8)8Me | (MM8)8Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-eeeeeee | Me | (MM8)8Me | (MM8)8Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MeM8M8M8 | Me | (MM8)8Me | (MM8)8Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MeMM8M8 | Me | (MM8)8MM | (MM8)8MM | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MeMM8M8 | Me | (MM8)8MMMM | (MM8)8MMMM | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| 8-MeM8MM8M8 | MMM | Me | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| |
Me | (MM8)8Me | (MM8)8Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| |
Me | (MM8)8MMMM | (MM8)8MMMM | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| |
Me | MMM | Me | 888, MM8Me8 | eeeeeee, 88°M | 88 | [888] |
| |
Me | |
Me | MeM≡Me[M(e-Me)Me8]8,e 8-M8MM8M8MM | eeeeeee ee MMMe8, ee, 88 eee | >88 | [888] |
| 8-eeeeeee | Me | 8-eeeeeee | Me | MeM≡Me[M(e-Me)Me8]8,e 8-M8MM8M8MM | 8,8,8-eeeeeeeeeeeeeeee, ee, 8 Meee, 88 eee | 88 | [888] |
| Me | Me | Me | Me | M8(MMMM)8e | eeeeeee, 88°M, 8 e | 88 | [888] |
| Me | Me | Me | Me | M8(MMMM)8e | eeeeeee, 88°M, 8 e | 88 | [888] |
| (MM8)8Me | M | (MM8)8Me | M | M8(MMMM)8e | eeeeeee, 88°M, 8 Meee, 8 e | 88 | [888] |
| (MM8)8Me | M | (MM8)8Me | M | 888 (Meeeeee) | eeeeeee, 88°M, 8 Meee, 8 eee | 88 | [888] |
| (MM8)8Me | M | (MM8)8Me | M | 888, e-MeMMe | eeeeeee, 88°M, 8 eee | 88 | [888] |
| Me | Me | Me | Me | 888 | ee, 888 Meee | 88 | [888] |
e Mee eeeeeeee eeeeeeeeee eee Meeeee 88.
e Meeeeeeeeee eeeeeee ee M8M≡MM8, M8M≡MM8, eee M8M≡MM8.
e MM eeeee.
e “Meeeeeeeeeee” eeeeeeee ee eeeeeee eeee eee-8-eee.
e Me8 = 8,8-Me8M8M8.
e MMMM = 8-eeeeeee-8-eeeeeeeeeeee-8-eeeee.
Meeeeeeeeeee Meeeeeeee
Meeeeee 888; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeeeeeeeeeeeee ee eeeeee eeeee.
Me(MM)8 (8.88 eeee), 8-MeM8M8MM (8.88 eeee), eee eeeeeeee eeeeee (8.8 eeee), Meeeeee (8.8 eM) ee eeeeeeee MMM eeeeeeee, eee eeeeeeeee 8,8-eeeeeeeeeeeeee (88 eM) eeee eeeeeee ee e 88-eM eeeee eeeeeeee eeee e eeeeee eeeeeeeee ee 88°M (eeeeee eeeeee) eeeee e eeeeee ee eeeee. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MM. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88–88%.
Meeeee 8-(8-Meeeeeeeee-8-eeee)eeeeeeee [888, M8 = 8-MeM8MM8M8; M8 = (MM8)8Me]; Meeeeee Meeeeeeee:[888]
MMMMMMM: Mee eeeeeee 888 eeeeeeeee eeeeeeeee eeeeeeee eeee ee eeee eeeeeeeeeee, ee eee eeeeeeeee eeeeeeee eee ee ee eeeeeee eee eeeeeeee eeeee ee eeeee eeeeeeeeee eeee eeeeeeeeeeeee eeeee eee eeeeeeee eeeeeeee eee eeeeeeee eeeeeeeee.
8,8-Meeeeeeeeee-8-eee (888 ee, 8.88 eeee) eee eeeeee eeee-8-eeeeeeeeeeee (888 ee, 8.88 eeee) eeee eeeee ee e eeee ee eeeeeee 888 (88 ee, 8.888 eeee) ee MM8Me8/eeeeeee (88:8; 888 eM) eee eee eeeeeee eee eeeeeee ee 88°M eee 8 e. Mee eeeeeee eee eeee eeeeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee, eeee eeeeeee/MeMMe 88:8) ee eeee e eeeeeeeee eee; eeeee: 888 ee (88%); 8M MMM (MM8Me8, δ): 8.88 (ee, 8M, M = 8.8, 8.8 Me), 8.88 (eee, 8M, M = 88.8, 8.8, 8.8 Me), 8.88 (ee, 8M, M = 8.8, 8.8 Me), 8.88 (e, 8M), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me).
References
| [193] | Meee, M., Me Mee Meeeeeeee ee Meeeeeeeee Meeeeeeee, Meeeee, M.; Meeeeee, M., Mee.; Meeee: Meeeeee, MM, (8888); e 888. |
| [194] | Meeee, M.; Meeee, M. M., Mee. Meeee. Meeee., (8888) 888, 88. |
| [195] | Müeeeeee, M.; Meeeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
| [196] | Meeeee, M., Me Meeeeee Meeeeeeee Meeeeeeeee M, Meeeeee, M.-M.; Meeee, M., Mee., Meeee-MMM: Meeeeeee, Meeeeee, (8888); e 88. |
| [197] | Müeeeeee, M.; Meeeee, M.; Meeeeee, M. M., Meee.–Mee. M., (8888) 8, 8888. |
| [198] | Müeeeeee, M.; Meeee, M.; Meeeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [199] | Meeee, M. M.; Meee, M. M.; Möee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [200] | Müeeeeee, M.; Meeeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
| [201] | Meee, M. M. M.; Meeeeeeeeee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me., (8888) 88, 888. |
| [202] | Meee, M. M. M., Mee. Meee. Mee., (8888) 88, 888. |
| [203] | Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [204] | Meeeeeee, M.; Meeee, M. M.; Meeeee, M. M., Meee. Meeeee., (8888), 8888. |
| [205] | Meeeeeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M., Meeeeeeeeeeeeee, (8888) 8, 8888. |
| [206] | Meeeeeee, M.; Meeeeeee, M. M.; Meeee, M. M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me., (8888) 88, 888. |
| [207] | Meeeeeee, M.; Meeeeeee, M.; Meeéeee, M.; Meeeee, M.-M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [208] | Meeeeeee, M.; Meeeeeeee, M., M. Mee. Meeee. M: Meee., (8888) 888, 88. |
| [209] | Meeeeeee, M.; Meeeeeeee, M. M.; Meeeeeeee, M.; Meeeeeeeeee, M., M. Mee. Meeee., (8888) 8, 88. |
| [210] | Meeeeeee, M.; Meeeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [211] | Meeeeeee, M. M.; Meee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [212] | Meeeeeeeeee, M.; Meeeee, M.; Meee, M. M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [213] | Mee, M.; Meeeeeee, M.; Meeeee-Meeeeee, M.; Meeeé, M.; Meeeeee, M.; Meeeeee, M.; Meeeeee, M., Mee M. Meee., (8888) 88, 8888. |
| [214] | Meeeeee, M.; Meee, M. M. M., Mee. Meee., (8888) 8, 8888. |
| [215] | Meeeeee, M.; Meeeeee, M.; Meeeeeee, M.-M.; Meeeeee, M.-M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [216] | Meeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [217] | Meeeee, M.; Meeeeee, M.; Meeee, M.-e.; Meeeee, M.; Meee, M., Meee. Meee., (8888), 8888. |
| [218] | Meeeee, M.; Meeeeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [219] | Meeeee, M.; Meeee, M.; Meee, M., Meee. Meee., (8888), 888. |
| [220] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeee, M., M. Mee. Meeee., (8888) 88, 88. |
| [221] | Meeee, M.; Meeeeeee, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [222] | Meeeeee, M. M., Me Meeeeeee ee Meeeeeeeee, Meeeee, M. M., Me.; Meeee-MMM: Meeeeeee, Meeeeee, (8888); Mee. 8, e 888. |
| [223] | Müeeeeee, M., Me Meeeeeee ee Meeeeeeeee, Meeeee, M. M., Me.; Meeee-MMM: Meeeeeee, Meeeeee, (8888); Mee. 8, e 888. |
| [224] | Meeeeeeeee, M. M.; Meeeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [225] | Meeeeee, M. M., Meee. Mee., (8888) 888, 888. |
| [226] | Meeeeeeee, M.; Meeeeeeeee, M.; Meee, M.-M.; Meeeeeee, M., Mee. Meeee. Meeee., (8888) 888, 8888. |
| [227] | Meee, M.; Meee, M. M.; Meeee, M. M.; Meeeeeeeee, M.; Meeeeeeeee, M.; Meee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [228] | Meeeeee, M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeeee, M.; eee Meee, M.-M.; Meee, M. M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [229] | Meee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [230] | Meeee, M.; Meeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 88.
Return to Top