You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via48.2.1.4.2 Variation 2: Cyclopropanation with Catalytically Generated Methylene
Please login to access the full content or check if you have access via
de Meijere, A.; Kozhushkov, S. I., Science of Synthesis, (2009) 48, 509.
Methylene can also be transferred to alkenes by employing diazomethane in the presence of a catalyst, e.g. copper(I) chloride, copper(I) bromide, copper(I) trifluoromethanesulfonate, palladium(II) acetate, or rhodium(II) acetate dimer.[162,163] (see also Houben–Weyl, Vol. E 17a, p 256 and Vol. E 19b, p 165). When diazomethane is passed through a solution of an alkene containing copper(I) chloride, no insertion products, such as those obtained from reactions of photochemically generated methylene with hydrocarbons, are found, and only the expected products of methylene addition to the double bond are produced.[164–166] The main drawback of this old and nowadays rarely applied Gaspar–Roth cyclopropanation protocol, originally going back to earlier work of Müller and co-workers,[167] is the nontrivial handling of explosive gaseous diazomethane, which makes such preparations dangerous, especially on larger scales. Nowadays, the usual protocol uses less dangerous solutions of diazomethane in diethyl ether[168] (less commonly in dichloromethane), and palladium(II) acetate[169,170] appears to be the most widely used among a variety of catalysts.[162,163,171] However, in hydrocarbon chemistry, i.e. for the cyclopropanation of inactivated double bonds, each variant of these cyclopropanations has its scope and limitations;[172] generally speaking, both of them are less efficient than Simmons–Smith cyclopropanations (see Section 48.2.1.4.3). In most cases, palladium catalysts provide better results than copper(I) salts; however, the structure of the starting materials is often more important than the nature of the catalyst. As a rule, alkenes with double bonds that are activated by strain give better yields. For example, under palladium(II) acetate catalysis, oct-1-ene and bicyclo[2.2.2]octene can be cyclopropanated in 38 and 64% yields, respectively.[173] The yields of bicyclo[2.1.0]pentane derivatives 102 increase with increasing strain in the cyclobutene precursor, even under catalysis with copper(I) salts (Scheme 33).[174–176]
Meeeee 88 Meeeeeeeeeeeeeee eeee Meeeeeeeeeee eeeee Meeeee(M) Meee Meeeeeeee[888–888]
| M8 | M8 | Meeeeeee | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | Me | MeMe | eeeeeee, 8°M | 88 | [888] |
| Me | Me | (MeMMe)8•M8M8 | Me8M, 8°M | 88 | [888] |
 |
MeMe | Me8M, 8°M | 88 | [888] | |
Me eeee ee eeeee eeeeeee, eee eeee eeeee ee eeeeeeeeeeeee (888) eeeeeeee eeee eeeeeeeeeeeeeeeee eeee eee eeeeeeeeeee eeeeee eeee, eeeeeeeee eeeeeee eeeeeeeeeeee eee eee eeeeeeeee eeeeee, eeeeeeeeeeee e eeeeeee eeeeeeeee ee eee eeeeee eeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeee Meeee Meeeeee Meeeeeeeeeee eeeee Meeeee(M) Meeeeeee Meeeeeeee[888]
Meeeeeeeeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeeee eeeeeeeeeee 888 eeeeeee ee eeee eeeeee eeeeeeeeeee eee-eeeeeeeeeeee 888 (Meeeee 88).[888,888,888] Mee eeeeee eeeeee eeee eee eeeeeeeeee eeeeeeee ee eeee ee ee eee eeeeee ee eeeeeeeeeeee ee eee eeeeeeee eeeeeeee 888. Meeeeee, eee ee eeeeee(M) eeeeeeee ee e eeeeeeee eee eeeeeeeeeee eeeeeeeeeee eeee ee 888 eeeeeeeee eeee eeeee eeeeeeeeee eeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeee eee Meeeeeeeeeeeeee Meeeeeeeeee eeee Meeeeeeeeeee eeeee Meeeeee Meeeeeeeee[888,888,888]
| M8 | M8 | M8 | M8 | Meeeeeee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|
| M | M | M | M | Me(eeee)8 | Me8M | 88 | [888] |
| M | M | M | M | Me(eeee)8 | MM8Me8 | 88 | [888] |
| M | M | M | M | Me(MMe)8 | MM8Me8 | 88 | [888] |
| M | M | M | M | MeMe | MM8Me8 | 88 | [888] |
| M | M | MM8 | Me(MMe)8 | MM8Me8 | 88 | [888] | |
| (MM8)8 | M | M | Me(MMe)8 | MM8Me8 | 88 | [888] | |
| (MM8)8 | MM8 | Me(MMe)8 | Me8M | 88 | [888] | ||
Meeeee 88 Meeeeeeeeeeeeeee ee e Meeeeeeeeee Meeeeeeeee eeee Meeeeeeeeeee[888]
Meeeeeeee eeeeee eeeee eee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeeeee; eeeeeee, eeee ee eee e eeeeeee eeee. Meee, eeeeeee[8.8.8]eeeeeee ee eeeeeeee eeee eeeeeeeeeee ee 88% eeeee ee eeeeeeeeeeeeeee eeeee eeeeeeeee eeee eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM),[888] eeeee eee eeeee ee eeeee[8.8]eeeeee (888) ee eeee 88% (Meeeee 88).[888] Meeeeeeee ee eeeeeeeeee, eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eeeee eee eeee eeeeeee eee eee eeeeeeeeeeeeeeee ee eeeeeeee eeeeee eeeee ee eeeeeeeeeeeeeeeeeeeeee (eeeeeeeeeeeeeeeeeeeee) ee eeee 888 ee eeeeeeeeeeeeeeeeeeeeeee ee eeee 888, eee eeee eee eeee eeeeee eeee ee e eeeeeeeeeee eeee ee eee eeeeeeeee ee eeeeeeeeeeee eeee eeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeee eeeee eeee, eee ee-eeeeee eeeeee [e]eeeeeeeeeeee 888.[888–888] Meeeeeeeeee ee eeeee eeeeeeeeeeeeeeeee eee eeeeee eeeeeeeeeeee; eeeeeee, eeeeeeee eeeeee eee eeeee. Meee eeeeeeee ee eeeeeeeeeeeeeeee eeee eeee, eeeee eeeeeeeee eeeeeeee eeeeeeeeeeee eeeeeeee eeeeeeeeeee eeeeeeee eeeeee eeee eee eee ee eee eeeeeee eeeeeeeeeeee ee eee σ-eeee eeeeeeeeee ee [e]eeeeeeeeeeee. Meee eeeeeeeee eeeeeee eeee σ-[e]eeeeeeeee, ee eeeeeee ee eee eeee-eeeee π-[e]eeeeeeeee eeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee.[8]
Meeeee 88 Meeeeeeee ee Meeee[8.8]eeeeee eee ee Meeeee [e]Meeeeeeeeeee ee Meeeeee eee Meeeeeeeeeeeeeee Meee Meeee ee Meeeeeeeeeeeeeee ee Meeeeee eeee Meeeeeeeeeee eeeee Meeeeeeee(MM) Meeeeee Meeeeeeee[888,888–888]
| Meeeee | e | Meeee (%) | Mee |
|---|---|---|---|
| 888 | 8 | 88 | [888] |
| 888 | 8 | 88 | [888] |
| 888e | 8 | 88 | [888] |
| 888e | 8 | 88 | [888] |
| 888 | 8 | 88 | [888] |
| 888e | 8 | 88 | [888] |
| 888 | 8 | 88 | [888] |
| 888e | 8 | 88 | [888] |
| 888e | 8 | 888 | [888] |
e Meeeeeeeeeeeeeee eeee eeeeeeeeeeee.
Meeeeee eee eeee eeeeeeeee eee eeee eeeeeee ee eee eeeeeeeeeee eeee ee eee eeeeeeeeeee ee eee eeeeeeee [e]eeeeeeeeeeee 888–888 (Meeeee 88).[8,8]
Meeeee 88 Meeeeeee Meeeeeeeeeee Meeeeeeeeee Meeee Meeeeeeeeeee eeeee Meeeeeeee(MM) Meeeeee Meeeeeeee[8,8]
Me eeeeeeeeeee eeeeeeeeeeee eeeeeee ee eeeeeeeeeeeeeeee eeee eeeeeeeeeeee eeeee eeeeeeeee(MM) eeeeeee eeeeeeeee ee eee ee-eeeeee “eeeeeeeee” eeeeee ee Meee.[888] Meeeeeeee ee eeee eeeeee, eee eeeeeeee eeeeee ee eeeee ee eee eeeeeee ee eee eeeeeeeee eeee ee eee eeeeee eee eeeeeeeeeeee. Me eeeee ee eeeee ee eeee eeeeee eeee eeeeeeeee, eeee eeeeeeeeeeee eeeee eeeeeeeee eeeeeee eee eeeeeeeeeeeeeeeee ee eeeeeeeeee[888] eee eeeeeeeeee eeeeeeeee[888–888] eeeeee eeeee. Meee, eeee eeeeeeeeeee eeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee ee M8-eeeeeeeeeeeeeeeeeeeeeee (888, e = 8)[888,888] eee M8-8,8,8,8-eeeeeeeeeeeeeeeeeeeeeeeeee (888),[888] eeee 888 (e = 8) eee 888, eeeeeeeeeeee, eee eeee ee eeeeeeee eeeee eeee eeeeee ee eeeeeeeeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeee-Meeeeeeeeee Meeee Meeee eee Meee Meeeeee ee Meeeeeeeeeeeeeee eeee Meeeeeeeeeee eeeee Meeeeeeee(MM) Meeeeee Meeeeeeee[888–888]
Me eeeeeee eeee eeeee, eeeeeee, eee eee Meeeee–Meee eeeeeeee (eeee MM8M8/MeMe) eee ee ee eeee. Meee eeeeeeeee eeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeeeeeeeee (888). Me eeeee ee eee eeee eeee eee eeeeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeeeee 888 eeeee eee eeeeeeeeeeeeeeee eeeeeee 888 ee eeee eeeee,[888] eee eee ee eeeeeeeeeeee–eeeeeeeee(MM) eeeeeee ee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee (888)[888] ee ee eeeeeeeeeeeeeeeeeeeeeeeee (888)[888] eeeeeeeee eeeeeeee ee eeeeeeee, eee eeeeeeeee eeee eeeeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee eeeee eeee eee eeeeeeeee eeeeee eeeeeeeeeeee, eeeee eeeeeeeeee eee e eeeeeeeeeeee eeee eeee. Me eee eeee ee eeeeeeeeeeee 888, eee eeeeeee[8.8.8.8]eeeeeee eeeeeee (88% eeeee) ee eeeeeeeeeee ee 88 eeeee eeeeeeeeee (Meeeee 88). Me eee eeeee eeee, eee eeee eee eee Meeeee–Meee eeeeeeee ee eeee eee eee eeeeeeeeeeeeeeee ee 888[888] eee 888[888] eeeeeee eeeee eeeeeeee (eeeeee eee eeeeee eeeee eeeee eeee ee ee eeeeeee), eee eee eeeeeeeeeeeeee eeeeeee ee eeee eeeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeee eeee eeeee eeeee eeeeeeeee eeeeeeeee ee eeeee Meeeeee–Meeee eeeeeeeeee. Me ee eeeeeeeee eeee eee eeeeeeeeeeeeeeeeee eeeeeeeeeee eeeee eee Meeeee–Meee eeeeeeeeee eeee ee eeeeee ee eeeeee(M) eeeee eeeeeeeee eeee eeeeeeeeeeee(M) eeeeeeeee ee eeeee eee eeeeee eeee ee eee eee-eeee;[888] eeeee eeeeee(M) eeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeee eeee eeeeee ee eee eeeeeeeee ee eee eeeeeeeeee eeee eeeeeeeee eeee-eeee. Meeeeeeee, eeeee ee eeeeeee eeeeeeeeee eee eeee eeeeeeee eeee eee eee eeeeeeeeeee ee eeee eeeeeee eeeeeeeee ee eee eeeeeeeeeeeeeeee eeee eeeeee [88]eeeeeeeeeee (M)-(−)-888 eeee (M)-888.[888]
Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeeee eee Meee-Meeeeeeee ee Meeeeeeeeeeeeeeeeeee Meeeeeeeeeeeeeeeeee eeeee Meeeeeeee Meeeeeeeee[888,888–888]
Mee eeeee eeeeeeeee ee eee eeeeeeeee-eeeeee eeeeee eeeeeeeeeeeeeeeeee (888), eeeeeee eeeeeeeeeeeeeeeee (888), eee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeeeeee (888) eeee eeee eeeeeeee eeeee eee Meeeee–Meee eeeeeeee (Meeeee 88).[88,888] Meeeeee, eee eeeeeeeeeeee eee eeeeeeee ee eee eeeeee ee eeeeeeee eeee eeee- eee eeeeeeeeeeeeeeeeee eeeeeeee.
Meeeee 88 Meeee Meeeeeeeeee ee Meeeeeeeeeeee Meeeeeeeeee Meeeeeeeeeee-Meeeeeeeee Meeeeeeee Meeee eee Meeeee–Meee Meeeeeee[88,888]
Me eeeeeeee eeee eeeeeee, eeeeeeeeeeeeeeee eeee ee eeee eeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee eeeeee eeee ee eeeeeeeee. Meee eeeeee, ee eeeee ee eeeeeeeee eee eeeeee, ee eee eeee eeeeeeeeee eee eee eeeeeee eeeeeeee [e]eeeeeeeeeeee, ee eee eeeeeeee eeeeee ee eeeeeeeeee eeee eee eeeeeeee ee eeee eeeee ee eeee eee eeeee eeeeeeee. Mee eeeee eeeeeeeeee eeeeeeeeeeee ee eeee eeeeeeee eeee eee eeeeeeeeeee ee [8]eeeeee (888) ee eee eeeeeeee ee ee eeee eeeeeeeee eeeeeeeeeeeeeeeee (888) eeee eeeeeeeeeeeeeeeeee (888)[888] eee eeee eee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeee M8e-888 (Meeeee 88).[888] Meeeeeeeee eeeeeee eee eeeeeeee eeee ee eeee eeeeeeeee 8-eeeeeeeeeeee[8.8.8.8]eeeeeee (888).[888,888] Meeeeeee, eee eeeeeee eeeee, eee eeeeeeeeee eeeeeeee ee eee eeee eeeeeeeeee eee, ee eeeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeeeeeeeee [8]eeeeee 888, e M8e-eeeeeeeee eeeeeeee [88]eeeeeeeeeee, eeee eeeeeeee 888.[888,888]
Meeeee 88 Meeeeeeeeeeeeeee eeee Me Meee Meeeeeeee Meeeeeeeeeeeeeee eee Meeeeeeeeeeeeeeeeeee Meeeeeeeeeeeeeeee[888,888–888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeeeeee Meeeeeeeeee 888; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee.
Me e eeee ee eee eeeeeeeeee eeeeeeeeee 888 (88 eeee) ee MM8Me8 (8 eM) eee eeeee eee eeeeeeee (8.8 eeee) ee eee eeeeeee. Mee eeeeeeeee eeeeeee eee eeeeee ee −88 ee 8°M, eee e eeeeeeeee 8.88 M eeee ee MM8M8 ee MM8Me8 (88 eM, 88 eeee) eee eeeee eeeeeeee, eeee eeeeeeee, eeee e eeeeee ee 8 e. Mee eeeeeeeeeee ee eee eeeeeee eee eeeeeeeee ee MM. Meee ee eee MM8Me8 eee eeee eeeeeeeeee, eeeeeee (8–8 eM) eee eeeee, eee eee eeeeeee eee eeeeeeee eeeeeee e eee ee eeeeeee eeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeee MM eee eeeeeeeeee ee eeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeeeee eeee eee eeeeeeeee eeee; eeeee: 88–88%.
Meeeee [e]Meeeeeeeeeee 888; Meeeeee Meeeeeeee:[888–888]
MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee.
M eeee ee MM8M8 [eeeeeeee eeee M-eeeeee-M-eeeeeeeeeee (88 eeee)][888] ee Me8M (88 eM) eee eeeee eeeeeeee ee −8 ee 8°M ee e eeeeeee eeee ee eee eeeeeeeeeee eeeeee 888 (8.88 eeee) ee eeeee 888 (8.88 eeee) eee Me(MMe)8 (8.88 eeee) ee Me8M (88 eM). Mee eeeeeee eee eeeeeeee eeeeeee e eee ee Meeeee eee eeeeeeeee eeeeeeeeeeee ee eeeeeee eeeeeeee. Mee eeeeeeeeeeee 888 eeee e = 8–8 eee eeeeeee eee eeee-ee-eeee eeeeeeeee eeeee eeeeeee eeeeeeee (8.88 Meee) eeee e eeee (−88°M) eeee; eee eeeeeeee ee eee eeee eeee eeeeeeee ee eeeeeeeeeee MM; eee eeeeeeeeeee 888 eeee e = 8 eee eeeeeee eee eeeeeeeeeeeeee (MeMM); eee eee eeeeeeeeeee 888 eeee e = 8 eee eeeeeee eee eeeeeeee ee 888°M/8.8 Meee; eeeee: 88–888%.
Meeeeeeeeeeeeeeeeeeeeee (888, e = 8); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee. Meee eeeeeeee eeeeeeee eeee eeeeeeeee.
Me e eeeeeeeee (−88°M) eeee ee MM8M8 [eeeeeeee eeee M-eeeeee-M-eeeeeeeeeee (8.88 e, 88.8 eeee)][888] eee 8,8-eeeeeeeeeeeeeeeeee-8,8-eeeee (888, e = 8; 8.88 e, 8.88 eeee) ee Me8M (888 eM) ee e 8-M Meeeeeeeee eeeee eee eeeee e eeee ee Me(MMe)8 (888 ee, 8.888 eeee) ee MM8Me8 (8 eM) ee eee eeeeeee. Mee eeeeeeeeeee eeeeeeeeeee eeee ee 88°M. Mee eeeeeee eee eeeeeee eee ee eeeeeeeeee 88 eee, eeeeeeee eeeeeee e eee ee Meeeee, eee eeeeeeeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeee ee eeee e eee eeeeeee ee MM8M8 eeee (888 eM) eee eee eeeeeeeee, eeee eee eeeeeeee ee Me(MMe)8 ee MM8Me8, eee eeeeeeee eeeeeee eeeee, eeee MM eeeeeeeeee eeeee eeee eeeeeeee ee MM8M8 eee Me(MMe)8. Meeee eee eeeeeeeeeee, eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee eeeeeeeeeee eeee 8% MeMM8, eeeeee) ee eeee e eeeeeeeee eeeeee; eeeee: 8.88 e (88%); 88% eeeeee. Me eeeeeeeeee eeeeee eee eeeeeeee ee eeeeeeeeeee MM; ee ee. −88°M; 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M, 8/8 ee 8MM8), 8.88–8.88 (e, 88M, 8/8 ee 8MM8+8MM); 88M MMM (MMMe8, δ): −8.8 (8MM8), 88.8 (8MM), 88.8 (M).
(8M,8M,8M,8M,8M,8M,88M,88M,88M,88M,88M,88M)-Meeeeeeeeeeeee[8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8]eeeeeeeeeeeee [(M)-(−)-888]; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee. Meeee-eeeee eeeeeeeeeeee eeeeeeeee ee eeee eeeeee eee eeeeeeeeeee eeeeeeeee.
M eeee ee MM8M8 ee Me8M [eeeeeeee eeee M-eeeeee-M-eeeeeeeeeee (8.88 e, 88.8 eeee)][888] eee eeeee eeeeeeee ee ee ee e eeeeeeeeee eeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeeeee eeeeeeeeee (M)-888 (88 ee, 8.888 eeee), MeMe (8.888 e, 88.88 eeee), eee Me(MMe)8 (888 ee, 8.888 eeee) ee Me8M (88 eM) eeee e eeeeee ee 8 e. Mee eeeeeee eee eeee eeeeeeee eeeeeee e eee ee Meeeee eee, eeeee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eeee eee eeee eeeeeeeeee ee eee eeeeeeee eeeee eeee eeeee. Meeeee eeeeeeeeeeeeee ee eee eeeee eeeeeee (eeeeee eee, eeeeee; Me 8.88) eeeeeeee e 8.8:8 eeeeeee ee eee eeeee eeeeeee eee eee eeeeeeee (8M,8M,8M,8M,8M,8M,88M,88M,88M,88M,88M,88M)-888; eeeee: 88 ee (88%). Meee eeeeeeee eeeeeeee (8 ee, 88%) eee eeee eeeeeeeee. Mee eeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeeee MMMM ee eeee eeeeeeeee eeeeee ee (8M,8M,8M,8M,8M,8M,88M,88M,88M,88M,88M,88M)-888; eeeee: 88 ee (88%); eee (M)-(−)-888; eeeee: 88 ee (88%). Meeeeeeeee eeeeeee eeee eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM). (M)-(−)-888 eeeeee eeeeeeee eeeee 888°M; ee 888°M; [α]M88 −8888.8 (e 8.888, MMMe8); 8M MMM (MMMe8, δ): 8.88 (e, 8M), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.88–8.88 (e, 88M), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.88 (e, 8M, M = 8.8 Me), 8.88–8.88 (e, 8M), 8.88–8.88 (e, 8M); 88M MMM (MMMe8, δ): 88.88 (8M), 88.88 (8M), 88.8 (8M), 88.8 (8M), 88.8 (MM8), 88.8 (8MM8), 88.8 (8MM8), 8.8 (8MM8), 8.8 (8MM8), 8.8 (8MM8), 8.8 (8MM8).
Meeeeeeee[8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8.8]eeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
M eeee ee eee M-eeeeeeeeeee eeeeeeeeee 888 (888 ee, 8.88 eeee) ee eeeeeeeeeeeeeeeeee (888; 8.88 e, 88.8 eeee) eee eeeeeeeeee eeeeeee eeee eeeeeeee MeMMe (888 ee, 88.8 eeee) ee 8°M eee e eeeeee ee 88 e. Mee eeeeeee eee eeeeeeee, eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee; Me 8.88) ee eeee eeeeeeeee eeeeeeee; eeeee: 88 ee (88%); ee 888–888°M; 8M MMM (MMMe8, δ): 8.88, 8.88 (e, MM′MM′, 88M); 88M MMM (MMMe8, δ): 8.8 (88MM8), 88.8 (8M), 88.8 (8M).
References
| [5] | ee Meeeeee, M.; Meeeeeeeee, M. M., Meee. Mee., (8888) 888, 88. |
| [6] | ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeeee, M., Meee. Mee., (8888) 888, 8888. |
| [7] | ee Meeeeee, M.; Meeeeeeeee, M., Mee. Meeeee Mee. Meee., (8888) 8, 888. |
| [28] | ee Meeeeee, M.; Meeeeeeeee, M.; Meeeeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [162] | Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M., Mee. Meee., (8888) 88, 888; Meee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 888. |
| [163] | Meeee, M. M.; MeMeeeee, M. M.; Me, M., Meeeee Meeeeeeee Meeeeee eee Meeeeee Meeeeeee eeee Meeee Meeeeeeee, Meeee: Meeeeee, (8888); ee 88, 888. |
| [164] | Meeeee, M., MeM Meeeee, Meee Meeeeeeeee, (8888). |
| [165] | Meeeeee, M. eee M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 888. |
| [166] | Meeeeeeee, M.; Meeeee, M. M.; Øeeeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeee, M.-M., Meee.–Mee. M., (8888) 8, 888. |
| [167] | Müeeee, M.; Meeeee, M.; Meeeee, M., M. Meeeeeeeeee., M, (8888) 88, 888. |
| [168] | Meeee, M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [169] | Meeeeeeee, M.; Meeeee, M. M.; Meeeeeé, M., Meeeeeeeeee Meee., (8888), 8888. |
| [170] | Meeeeeee, M.; Meeeeüeeee, M., Meeeeeeee, (8888), 888. |
| [171] | Meeeñe, M. M.; Meeeeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [172] | Meeeeee, M. M., Meeeeeeee, (8888), 88. |
| [173] | Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeeeee, M. M.; Meeeeee, Me. M.; Meeeeee, M. M.; Meeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 8888. |
| [174] | Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [175] | Meeeee, M. M.; Meee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
| [176] | Mee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [177] | ee Meeeeee, M.; Müeeee, M.; Meeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888), 888. |
| [178] | Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, Me. M., Mee. Meee. Meee, Mee. Meee., (8888), 888; Meee. Meee. Meee., (8888) 88, 888. |
| [179] | Meeeeeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., Me. Mee. Meee., (8888) 88, 888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
| [180] | Meeeee, M.; Meeee, M. M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [181] | Meeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 888. |
| [182] | Meeeeee, M. M.; Meeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., Me. Mee. Meee., (8888) 88, 888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
| [183] | ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M.; Meeee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [184] | ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M.; Meeeeeeeeeeee, M.; Meeeee, M.; Meeee, M. M.; Meeeee, M. M. M., Meee.–Mee. M., (8888) 8, 888. |
| [185] | Meeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [186] | ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meeeee, M. M. M.; Meeeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeeee, M. M.; Meeeeeeeeeeee, M. M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeee, M., Meee.–Mee. M., (8888) 88, 8888. |
| [187] | ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeee, M.; Meeeeeee, M.; Meeeeeeee, M. M.; Meeeeeeeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [188] | Meee, M., Meeeeeeee, (8888), 888. |
| [189] | Meeeeeeee, M. M.; Meeeeeeee, M. M. M.; ee Meee, M. M.; Meeeeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [190] | Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeee, M.; Meeee-Meeeeeee, M.; Meeeeeeee, M. M.; Meeeeeeeeeeee, M.; Meeeeeeee, M.; ee Meeeeee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me., (8888) 88, 888. |
| [191] | Meeeeeee, M. M.; ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [192] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 888. |
| [193] | Meeeeeeeee, M. M.; Meeee, M. M.; Meeee, M.; Meäeee, M.; Meeeeeeee, M. M.; ee Meeeeee, M., Mee. M. Mee. Meee., (8888), 8888. |
| [194] | Meeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, Me. M.; Meeeeee, M. M., Me. Mee. Meee., (8888) 88, 888; Meee. M. Mee. Meee. (Meee. Meeeee.), (8888) 88, 888. |
| [195] | Meeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeee', M. M.; Meeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 8888. |
| [196] | Meeee, M. M.; Meeeeee, M. M., Meee. Meee. Meee MMMM, (8888) 888, 888; Meee. Meee. (Meee. Meeeee.), (8888) 888, 888. |
| [197] | Meeeee, M.; Meeee, M.-M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [198] | Meeeee, M.; Meeee, M.-M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [199] | Meeee, M.; ee Meeeeee, M., Meee. Mee., (8888) 888, 8888. |
| [200] | Meeeeee, M. M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M.; Meeee, M.; ee Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [201] | Meeeeeeeee, M. M.; Meeeeee, M.; Meeee, M.; ee Meeeeee, M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [202] | ee Meeeeee, M.; eee Meeeeee, M.; Möeeeee, M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeee, M.; Meeee-Meeeeeee, M.; Meeee, M. M.; Meeeee, M. M. M., Meee.–Mee. M., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 88.
Return to Top