CN106928128B - A kind of alkyl diradical and preparation method thereof - Google Patents
A kind of alkyl diradical and preparation method thereof Download PDFInfo
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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Abstract
A kind of Novel alkyl free radical and preparation method thereof, with R-BF3K is raw material, in a nitrogen atmosphere, using toluene as solvent, with silver oxide and water initiated oxidation reduction system, is captured by TEMPO, and R-O-TMP is generated.Three potassium fluoborate simplicity of alkyl in raw material of the present invention is easy to get, and stability is high and nontoxic.The preparation method of radical initiator in the present invention, react several minutes can be completed at room temperature, fast and simple, and yield is high.Furthermore the substrate applicability that the present invention uses is wide, aromatic ring, heteroaromatic, ketone carbonyl and ester group can be compatible with, and not by steric interference, to the 1 of big steric hindranceoAlkane, 2oAlkane and 3oAlkane is equally applicable.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of novel preparation method of alkyl diradical.
Background technique
The application potential of free-radical chemistry was excavated by chemists in recent years, because its unique chemical property is having
Play the role of in machine synthesis chemistry very important.Currently, how to prepare higher, the compatible more preceding free radical of activity at
For one of the problem of people's challenge.
Conventional obtains free radical by oxidation reaction, such as with organomagnesium reagent, organolithium reagent organometallic reagent
Method, the drawbacks such as that there are reaction conditions is excessively harsh, functional group's tolerance is weak.The present invention passes through the oxidation organic gold of other types
Belong to reagent and its derivative obtains corresponding free radical.It is deposited with such a can stablize in air of organic three potassium fluoborates salt
, and the higher reagent of reactivity is raw material in organic chemical reactions, by being aoxidized to organic three potassium fluoborates salt
Reaction, obtains corresponding free radical.
Alkyl trifluoroborate, silver oxide and water can be generated free radicals efficiently and rapidly at room temperature in this patent, and
It is captured by free radical scavenger, this provides a kind of new road synthetic route for the formation of free radical.
Summary of the invention
In order to overcome the above-mentioned deficiency of the prior art, the object of the present invention is to provide a kind of preparations of alkyl diradical
New method passes through 2,2,6,6- tetramethyl of free radical scavenger using alkyl trifluoroborate, silver oxide and water as initiation system
The free radical that piperidine oxide capture reaction generates, to generate a kind of stable free radical.Alkyl three in raw material of the present invention
Potassium fluoborate simplicity is easy to get, and stability is high and nontoxic.The preparation method of radical initiator in the present invention, at room temperature stoichiometric number
Minute can be completed, fast and simple, and yield is high.
To achieve the above object, the technical solution adopted by the present invention is that:
The alkyl diradical captured by radical-scavenging base TEMPO, shown in general structure such as formula (I):
R-O-TMP (Ⅰ)
In formula, R base is
One of, the structure of TMP base is
A kind of novel preparation method of alkyl diradical, with R-BF3K is raw material, in a nitrogen atmosphere, using toluene as solvent,
It with silver oxide and water initiated oxidation reduction system, is captured by TEMPO, generates R-O-TMP, synthetic route such as formula (II) institute
Show:
Specific synthesis step of the invention is as follows:
1) R-BF by metering is sequentially added in clean reactor3K, silver oxide and TEMPO substitute nitrogen 3 times,
Toluene-the water mixed solvent for injecting 10mL/mmol into reaction tube under nitrogen stream environment, seals reactor；
2) it is vigorously mixed at room temperature for 10~30 minutes, stops stirring, obtain reaction solution；
3) metallic residue in above-mentioned reaction solution is filtered out with diatomite, filter cake is washed 3~5 times with ethyl acetate, is merged
Filtrate is spin-dried for solvent, is separated by column chromatography chromatogram to get target product is arrived.
The R-BF3K is three potassium fluoborate salt of alkyl, shown in general structure such as formula (III):
R-BF3K (Ⅲ)
In formula, R base is
One of.
The TEMPO is 2,2,6,6- tetramethyl piperidine oxides.1
The R-BF3K, silver oxide and TEMPO are measured with molar ratio 1:1:1.
Toluene-water mixed solvent in the step 1) is made by the toluene and water of volume ratio 50:1.
Detailed description of the invention
Fig. 1 is the schematic diagram of 13 kinds of alkyl trifluoroborate structural formulas；
Fig. 2 is alkyl diradical in 13 captured by free radical scavenger TEMPO；
Fig. 3 is the nucleus magnetic hydrogen spectrum of compound (10)；
Fig. 4 is that the nuclear-magnetism carbon of compound (10) is composed；
Fig. 5 is the nucleus magnetic hydrogen spectrum of compound (12)；
Fig. 6 is that the nuclear-magnetism carbon of compound (12) is composed；
Fig. 7 is the nucleus magnetic hydrogen spectrum of compound (13)；
Fig. 8 is that the nuclear-magnetism carbon of compound (13) is composed；
Fig. 9 is that three potassium fluoborate of alkyl forms free radical, by the schematic diagram of radical scavenger TEMPO catching method.
Specific embodiment
The present invention is described in detail with reference to the accompanying drawings and examples, but the present invention is not limited to following embodiment.
Embodiment 1:
Three potassium fluoborate salt (19.8mg, 0.1mmol, 1.0eq.) of benzyl, oxygen are sequentially added in dry 10mL reaction tube
Change silver-colored (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol, 1.0eq.),
It substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw reaction tube
Lid, is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution uses diatom first
Soil filters out metallic residue, and filter cake is washed three times with ethyl acetate, merging filtrate, is separated after being spin-dried for solvent by column chromatography chromatogram
23.5 milligrams of colourless oil liquid are obtained, yield 95%.
1H NMR(400MHz,CDCl3)δ7.33(m,5H),4.82(s,2H),1.50(m,4H),1.33(m,2H),1.25
(s,6H),1.15(s,6H)；
13C NMR(100MHz,CDCl3)δ128.3,127.6,127.4,60.1,39.9,33.2,20.4,17.2,17.2；
Embodiment 2:
Three potassium fluoborate salt (21.2mg, 0.1mmol, 1.0eq.) of phenethyl is sequentially added in dry 10mL reaction tube,
Silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol,
1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw
Reaction lid is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution is first
Metallic residue is filtered out with diatomite, filter cake is washed three times with ethyl acetate, merging filtrate, is spin-dried for chromatographing color by column after solvent
Compose 25.3 milligrams of isolated colourless oil liquid, yield 97%.
1H NMR(400MHz,CDCl3) δ 7.18 (m, 5H), 3.87 (t, J=6.8Hz, 2H), 2.75 (t, J=6.8Hz,
2H),1.34(m,4H),1.24(m,2H),0.99(s,12H)；
13C NMR(100MHz,CDCl3)δ138.6,128.1,127.1,124.9,58.7,38.6,34.4,32.0,
19.1,16.1；
Embodiment 3:
Three potassium fluoborate salt (22.6mg, 0.1mmol, 1.0eq.) of phenylpropyl is sequentially added in dry 10mL reaction tube,
Silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol,
1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw
Reaction lid is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution is first
Metallic residue is filtered out with diatomite, filter cake is washed three times with ethyl acetate, merging filtrate, is spin-dried for chromatographing color by column after solvent
Compose 26.1 milligrams of isolated colourless oil liquid, yield 95%.
1H NMR(400MHz,CDCl3) δ 7.20 (t, J=7.1Hz, 2H), 7.14-7.08 (m, 3H), 3.70 (t, J=
6.3Hz, 2H), 2.63 (t, J=7.8Hz, 2H), 1.82-1.75 (m, 2H), 1.47 (m, 1H), 1.37-1.35 (m, 4H),
1.25-1.19(m,1H),1.06(s,6H),1.04(s,6H)；
13C NMR(100MHz,CDCl3)δ142.4,128.4,128.3,125.7,59.7,39.7,33.1,32.8,
30.5,20.1,17.2；
HRMS(ESI+):Calculated for C18H29NO[M+H]276.2327,found 276.2322.
Embodiment 4:
Sequentially added in dry 10mL reaction tube three potassium fluoborate salt of thienylethyl (21.8mg, 0.1mmol,
1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg,
0.1mmol, 1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene into reaction tube under nitrogen stream environment and 20.0 μ L steam
Distilled water screws reaction lid, is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.
Reaction solution filters out metallic residue with diatomite first, and filter cake is washed three times with ethyl acetate, merging filtrate, leads to after being spin-dried for solvent
Cross 25.4 milligrams of the isolated colourless oil liquid of column chromatography chromatogram, yield 95%.
1H NMR(400MHz,CDCl3) δ 7.13 (d, J=5.0Hz, 1H), 6.93 (d, J=4.9Hz, 1H), 6.84 (d, J
=2.8Hz, 1H), 3.96 (t, J=6.8Hz, 2H), 3.05 (t, J=6.8Hz, 2H), 1.42 (m, 4H), 1.32 (m, 2H),
1.11(s,12H)；
13C NMR(100MHz,CDCl3)δ141.9,126.5,125.1,123.4,59.8,53.4,39.7,33.0,
29.4,20.2,17.1；
Embodiment 5:
Three potassium fluoborate salt (16.4mg, 0.1mmol, 1.0eq.) of isobutyl group is sequentially added in dry 10mL reaction tube,
Silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol,
1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw
Reaction lid is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution is first
Metallic residue is filtered out with diatomite, filter cake is washed three times with ethyl acetate, merging filtrate, is spin-dried for chromatographing color by column after solvent
Compose 20.2 milligrams of isolated colourless oil liquid, yield 95%.
1H NMR(400MHz,CDCl3) δ 3.56 (d, J=6.4Hz, 2H), 1.88 (m, 1H), 1.45 (m, 4H), 1.33 (m,
2H),1.18(s,6H),1.14(s,6H),0.97(s,3H),0.95(s,3H)；
13C NMR(100MHz,CDCl3)δ83.0,59.8,39.7,33.1,28.2,20.2,19.7,19.1,17.2；
Embodiment 6:
Sequentially added in dry 10mL reaction tube spiral shell [4,5] decyl -6- methyl trifluoro boric acid sylvite (25.8mg,
0.1mmol, 1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides
(15.6mg, 0.1mmol, 1.0eq.) substitutes nitrogen three times, under nitrogen stream environment into reaction tube inject 1.0mL toluene and
20.0 μ L distilled water, screw reaction lid, are vigorously mixed at room temperature for 10 minutes, react and are clear that silver mirror on tube wall
Formation.Reaction solution filters out metallic residue with diatomite first, and filter cake is washed three times with ethyl acetate, and merging filtrate is spin-dried for
Pass through 28.2 milligrams of the isolated colourless oil liquid of column chromatography chromatogram, yield 92% after solvent.
1H NMR(400MHz,CDCl3) δ 3.81 (q, J=5.5,8.4Hz, 1H), 3.59 (t, J=8.5Hz, 1H), 1.90-
1.82(m,1H),1.69-1.27(m,20H),1.21-1.12(m,8H),1.10(s,6H)；
13C NMR(100MHz,CDCl3)δ78.8,59.7,59.6,49.2,44.0,39.7,38.3,35.8,33.2,
33.1,33.0,28.7,26.7,24.1,22.9,20.2,20.2,17.2；
Embodiment 7:
Sequentially added in dry 10mL reaction tube three potassium fluoborate salt of 4 butyric acid carbobenzoxy group (28.4mg, 0.1mmol,
1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg,
0.1mmol, 1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene into reaction tube under nitrogen stream environment and 20.0 μ L steam
Distilled water screws reaction lid, is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.
Reaction solution filters out metallic residue with diatomite first, and filter cake is washed three times with ethyl acetate, merging filtrate, leads to after being spin-dried for solvent
Cross 32.6 milligrams of the isolated colourless oil liquid of column chromatography chromatogram, yield 98%.
1H NMR(400MHz,CDCl3) δ 7.28 (m, 5H), 5.05 (s, 2H), 3.69 (t, J=6.0Hz, 2H), 2.52 (t,
J=7.6Hz, 2H), 1.91 (m, 2H), 1.35 (m, 4H), 1.22 (m, 2H), 1.05 (s, 6H), 1.00 (s, 6H)；
13C NMR(100MHz,CDCl3)δ172.4,135.1,128.0,127.5,127.2,74.3,65.2,58.8,
38.6,32.1,30.4,23.2,19.1,16.1；
Embodiment 8:
Sequentially added in dry 10mL reaction tube three potassium fluoborate salt of propione base (19.2mg, 0.1mmol,
1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg,
0.1mmol, 1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene into reaction tube under nitrogen stream environment and 20.0 μ L steam
Distilled water screws reaction lid, is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.
Reaction solution filters out metallic residue with diatomite first, and filter cake is washed three times with ethyl acetate, merging filtrate, leads to after being spin-dried for solvent
Cross 23.4 milligrams of the isolated colourless oil liquid of column chromatography chromatogram, yield 97%.
1H NMR(400MHz,CDCl3) δ 3.99 (t, J=6.0Hz, 2H), 2.59 (t, J=6.0Hz, 2H), 2.52 (t, J
=7.2,14.4Hz, 2H), 1.42 (m, 4H), 1.12 (m, 2H), 1.07 (s, 6H), 1.05 (s, 6H)；
13C NMR(100MHz,CDCl3)δ209.3,71.0,58.7,40.4,38.6,36.0,31.9,19.1,16.1,
6.6；
Embodiment: 9:
Sequentially added in dry 10mL reaction tube three potassium fluoborate salt of ethyl propionate base (24.4mg, 0.1mmol,
1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg,
0.1mmol, 1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene into reaction tube under nitrogen stream environment and 20.0 μ L steam
Distilled water screws reaction lid, is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.
Reaction solution filters out metallic residue with diatomite first, and filter cake is washed three times with ethyl acetate, merging filtrate, leads to after being spin-dried for solvent
Cross 23.1 milligrams of the isolated colourless oil liquid of column chromatography chromatogram, yield 95%.
1H NMR(400MHz,CDCl3) δ 4.00 (t, J=6.4Hz, 2H), 3.70 (s, 3H), 2.52 (t, J=6.4Hz,
2H),1.43(m,4H),1.26(m,2H),1.16(s,6H),1.06(s,6H)；
13C NMR(100MHz,CDCl3)δ172.3,71.6,59.8,51.6,39.7,34.0,33.0,20.0,17.2；
Embodiment 10:
Sequentially added in dry 10mL reaction tube three potassium fluoborate salt of 2- methvl-propionic acid methyl este base (25.6mg,
0.1mmol, 1.0eq.), silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides
(15.6mg, 0.1mmol, 1.0eq.) substitutes nitrogen three times, under nitrogen stream environment into reaction tube inject 1.0mL toluene and
20.0 μ L distilled water, screw reaction lid, are vigorously mixed at room temperature for 10 minutes, react and are clear that silver mirror on tube wall
Formation.Reaction solution filters out metallic residue with diatomite first, and filter cake is washed three times with ethyl acetate, and merging filtrate is spin-dried for
Pass through 24.0 milligrams of the isolated colourless oil liquid of column chromatography chromatogram, yield 93% after solvent.(nucleus magnetic hydrogen spectrum such as attached drawing 3,
Nuclear-magnetism carbon spectrum such as Fig. 4)
1H NMR(400MHz,CDCl3) δ 4.04 (t, J=7.6Hz, 2H), 3.96 (t, J=5.6Hz, 2H), 3.83 (s,
3H), 2.83 (q, J=6.0,12.0Hz, 1H), 1.56 (m, 4H), 1.43 (m, 2H), 1.33 (s, 3H), 1.27 (s, 6H), 1.20
(s,6H)；
13C NMR(100MHz,CDCl3)δ175.4,77.8,60.1,51.8,39.9,39.6,33.0,20.2,17.3,
14.2；
Embodiment 11:
Three potassium fluoborate salt (19.0mg, 0.1mmol, 1.0eq.) of cyclohexyl is sequentially added in dry 10mL reaction tube,
Silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol,
1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw
Reaction lid is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution is first
Metallic residue is filtered out with diatomite, filter cake is washed three times with ethyl acetate, merging filtrate, is spin-dried for chromatographing color by column after solvent
Compose 23.4 milligrams of isolated colourless oil liquid, yield 98%.
1H NMR(400MHz,CDCl3) δ 3.60 (m, 1H), 2.05 (m, 2H), 1.75 (m, 2H), 1.57 (d, J=
14.6Hz,2H),1.46(m,4H),1.24(m,6H),1.14(s,12H)；
13C NMR(100MHz,CDCl3)δ81.7,59.6,40.3,34.5,32.9,26.0,25.1,20.3,17.4；
Embodiment 12:
Three potassium fluoborate salt (17.6mg, 0.1mmol, 1.0eq.) of cyclopenta is sequentially added in dry 10mL reaction tube,
Silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol,
1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw
Reaction lid is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution is first
Metallic residue is filtered out with diatomite, filter cake is washed three times with ethyl acetate, merging filtrate, is spin-dried for chromatographing color by column after solvent
Compose 21.6 milligrams of isolated colourless oil liquid, yield 96%.(nucleus magnetic hydrogen spectrum such as attached drawing 5, nuclear-magnetism carbon spectrum such as Fig. 6)
1H NMR(400MHz,CDCl3) δ 4.31 (q, J=6.7,13.3Hz, 1H), 2.00 (d, J=7.7Hz, 2H), 1.69
(m,4H),1.50(m,6H),1.34(m,2H),1.20(s,6H),1.13(s,6H)；
13C NMR(100MHz,CDCl3)δ87.2,58.5,39.2,31.7,22.4,16.3；
Embodiment 13:
Three potassium fluoborate salt (16.4mg, 0.1mmol, 1.0eq.) of tert-butyl is sequentially added in dry 10mL reaction tube,
Silver oxide (25.4mg, 0.1mmol, 1.0eq.) and 2,2,6,6- tetramethyl piperidine oxides (15.6mg, 0.1mmol,
1.0eq.), it substitutes nitrogen three times, injects 1.0mL toluene and 20.0 μ L distilled water into reaction tube under nitrogen stream environment, screw
Reaction lid is vigorously mixed at room temperature for 10 minutes, reacts the formation that silver mirror is clear that on tube wall.Reaction solution is first
Metallic residue is filtered out with diatomite, filter cake is washed three times with ethyl acetate, merging filtrate, is spin-dried for chromatographing color by column after solvent
Compose 20.9 milligrams of isolated colourless oil liquid, yield 98%.(nucleus magnetic hydrogen spectrum such as attached drawing 7, nuclear-magnetism carbon spectrum such as Fig. 8)
1H NMR(400MHz,CDCl3)1.39(m,4H),1.21(m,11H),1.05(s,6H),1.00(s,6H)；
13C NMR(100MHz,CDCl3)δ59.2,41.0,35.0,29.6,20.6,17.3。
Claims (2)
1. a kind of preparation method of alkyl diradical, which is characterized in that with R-BF3K is raw material, in a nitrogen atmosphere, is with toluene
Solvent is captured with silver oxide and water initiated oxidation reduction system by TEMPO, generates R-O-TMP, R-BF3K is alkyl trifluoro
Boric acid sylvite, general structure is as shown in public formula (I):
R-BF3K (I)
In formula, R base is
One of；
Shown in its synthetic route such as formula (II):
In order to realize said synthesis route, synthesis step is as follows:
1) R-BF by metering is sequentially added in clean reactor3K, silver oxide and TEMPO substitute nitrogen 3 times, in nitrogen
Toluene-water mixed solvent is injected under air-flow environment into reaction tube, is mixed by toluene-water that toluene and the water of volume ratio 50:1 are made into
Bonding solvent seals reactor；
2) it is vigorously mixed at room temperature for 10~30 minutes, stops stirring, obtain reaction solution；
3) metallic residue in above-mentioned reaction solution being filtered out with diatomite, filter cake is washed 3~5 times with ethyl acetate, merging filtrate,
It is spin-dried for solvent, is separated by column chromatography chromatogram to get target product is arrived.
2. a kind of preparation method of alkyl diradical according to claim 1, which is characterized in that the R-BF3K, it aoxidizes
Silver and TEMPO are measured with molar ratio 1:1:1.
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| EP0467850A1 (en) * | 1990-07-20 | 1992-01-22 | Ciba-Geigy Ag | Stabilized monomer compositions |
| CN1823042A (en) * | 2003-07-14 | 2006-08-23 | 西巴特殊化学品控股有限公司 | Hydrogen peroxide catalyzed process for the preparation of sterically hindered n-hydrocarbyloxyamines |
-
2017
- 2017-03-13 CN CN201710144934.6A patent/CN106928128B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0467850A1 (en) * | 1990-07-20 | 1992-01-22 | Ciba-Geigy Ag | Stabilized monomer compositions |
| CN1823042A (en) * | 2003-07-14 | 2006-08-23 | 西巴特殊化学品控股有限公司 | Hydrogen peroxide catalyzed process for the preparation of sterically hindered n-hydrocarbyloxyamines |
Non-Patent Citations (2)
| Title |
|---|
| A new mild radical route to 3-substituted maleimides using organoboroles;Peter Birch ，等;《Tetrahedron Letters》;20111208;第53卷;第822-824页 * |
| Visible Light-Induced Selective Generation of Radicals from Organoborates by Photoredox Catalysis;Yusuke Yasu，等;《Adv. Synth. Catal.》;20121204;第354卷(第18期);第3414-3420页 * |
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