CS274226B1 - Substituted 1,1,3-trichloro-3-phenylpropanes and method of their preparation - Google Patents
Substituted 1,1,3-trichloro-3-phenylpropanes and method of their preparation Download PDFInfo
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- CS274226B1 CS274226B1 CS719788A CS719788A CS274226B1 CS 274226 B1 CS274226 B1 CS 274226B1 CS 719788 A CS719788 A CS 719788A CS 719788 A CS719788 A CS 719788A CS 274226 B1 CS274226 B1 CS 274226B1
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- YLCJXUZOSVMTBJ-UHFFFAOYSA-N 1,3,3-trichloropropylbenzene Chemical class ClC(Cl)CC(Cl)C1=CC=CC=C1 YLCJXUZOSVMTBJ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 23
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229940045803 cuprous chloride Drugs 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 150000003440 styrenes Chemical class 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 12
- 238000003760 magnetic stirring Methods 0.000 description 7
- -1 1,1,3-trichloro-3- (p-methylphenyl) propane Chemical compound 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
- FXGGVHPRMRPZIS-UHFFFAOYSA-N 1-chloro-4-(1,3,3-trichloropropyl)benzene Chemical compound ClC(Cl)CC(Cl)C1=CC=C(Cl)C=C1 FXGGVHPRMRPZIS-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- SYZVQXIUVGKCBJ-UHFFFAOYSA-N 1-ethenyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(C=C)=C1 SYZVQXIUVGKCBJ-UHFFFAOYSA-N 0.000 description 1
- JWVTWJNGILGLAT-UHFFFAOYSA-N 1-ethenyl-4-fluorobenzene Chemical compound FC1=CC=C(C=C)C=C1 JWVTWJNGILGLAT-UHFFFAOYSA-N 0.000 description 1
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Vynález se týká nových 1,1,3-trichlor-3-fenylpropanů substituovaných na benzenovém jádře různými skupinami a způsobu jejich přípravy.The invention relates to novel 1,1,3-trichloro-3-phenylpropanes substituted on the benzene ring by various groups and to a process for their preparation.
Substituované 1,1,3-trichlor-3-fenylpropany nebyly dosud známy ani v literatuře popsány, protože je nebylo možné připravit známými metodami. Tyto nové látky by bylo teoreticky možné získat reakcí substituovaných styrenů s chloroformem, avšak známé klasické provedení těchto reakcí pomocí iniciátorů (organické peroxidy, UV zářeni a podobně tvorbu požadovaných produktů neumožňuje, protože dochází v takových případech k přednostní polymeraci výchozích styrenů. Odstranění výše uvedené překážky a snadnost přípravy substituovaných 1,1,3-trichlor-3-fenylpropanů pomocí katalyzovaných reakcí popisuje tento vynález.Substituted 1,1,3-trichloro-3-phenylpropanes have not been known or described in the literature yet, since they could not be prepared by known methods. These new substances would theoretically be obtained by reacting substituted styrenes with chloroform, but the known classical performance of these reactions with initiators (organic peroxides, UV radiation and the like) does not allow the formation of the desired products, since in such cases preferential polymerization of the starting styrenes occurs. and the ease of preparing substituted 1,1,3-trichloro-3-phenylpropanes by catalyzed reactions is described in the present invention.
Předmětem vynálezu jsou substituované 1,1,3-trichlor-3-fenylpropany obecného vzorceThe present invention provides substituted 1,1,3-trichloro-3-phenylpropanes of formula
OCHC1CH2CHC12 kde R je metyl, fluor, chlor, brom nebo nitroskupina v poloze meta nebo para a způsob jejich přípravy reakcí 1 dílu mol. substituovaného styrenu obecného vzorce IIOCHC1CH CHC1 2 2 wherein R is methyl, fluoro, chloro, bromo or nitro in the meta or para position and their preparation by reacting 1 mol. of substituted styrene of formula II
A A_CH2 = CH2 kde R1 má shora uvedený význam, s 1 až 20 díly chloroformu v přítomnosti katalytického systému vytvořeného z 0,01 až 0,1 dílu mol. chloridu měďného a 0,01 až 1,0 dílu mol.A A-CH 2 = CH 2 wherein R 1 is as defined above, with 1 to 20 parts of chloroform in the presence of a catalytic system formed from 0.01 to 0.1 parts of mol. cuprous chloride and 0.01 to 1.0 part mol.
1,10-fenantrolinu nebo aminu obecného vzorce III1,10-phenanthroline or an amine of formula III
R2-NH-R3 R 2 -NH-R 3
3 3 kde R je vodík nebo skupina R a R je normální nebo rozvětvený C^ až C^ alkyl nebo Cg cykloalkyl nebo fenyl nebo benzyl, zahříváním reakční směsi při 20 až 150 °C.Wherein R is hydrogen or a group R and R is normal or branched C 1 -C 4 alkyl or C 8 cycloalkyl or phenyl or benzyl, by heating the reaction mixture at 20 to 150 ° C.
Tímto jednoduchým způsobem lze připravit požadované produkty v dobrýéh až vysokých výtěžcích (55 až 95 %). Jejich struktura byla ověřena pomocí elementární a NMR analýzy.In this simple manner, the desired products can be prepared in good to high yields (55-95%). Their structure was verified by elemental and NMR analysis.
Uvedené příklady blíže popisují způsob přípravy substituovaných 1,1,3-trichlor-3-fenylpropanů, aniž by omezovaly nebo vymezovaly rozsah jeho platnosti.The examples described in more detail describe the preparation of substituted 1,1,3-trichloro-3-phenylpropanes without limiting or limiting its scope.
Přiklad 1Example 1
Směs 1,2 g (0,01 mol) p-metylstyrenu, 11,9 g (0,1 mol) chloroformu, 0,05 g (0,5 mmol) chloridu měďného a 0,15 g (2 mmol) dietylaminu se zahřívá v zatavené skleněné smpuli za magnetického míchání v atmosféře dusíku při 90 °C po dobu 5 h. Chromatografický výtěžekA mixture of 1.2 g (0.01 mol) of p-methylstyrene, 11.9 g (0.1 mol) of chloroform, 0.05 g (0.5 mmol) of copper (I) chloride and 0.15 g (2 mmol) of diethylamine was added. Heat in a sealed glass tube under magnetic stirring at 90 ° C for 5 h under magnetic stirring. Chromatographic yield
1,1,3-trichlor-3-(p-metylfenyl)propanu zjištěný analýzou reakční směsi činí 90 %. Produkt o t.r. 78 °C/40 Pa se izoluje destilací za sníženého tlaku po odpaření nadbytečného chloroformu .The yield of 1,1,3-trichloro-3- (p-methylphenyl) propane was 90%. Product o t.r. 78 ° C / 40 Pa was isolated by distillation under reduced pressure after evaporation of the excess chloroform.
Pro C^gH^Clj (237,56) vypočteno: 50,56 % C, 4,63 % H, 44,81 '-i Cl; nalezeno:For C 4,6 gHH ^Clj (237.56) calculated: 50.56% C, 4.63% H, 44.81'-Cl; found:
50,63¾ C, 4,21 -s H, 45,01 % Cl.50.63 ° C, 4.21-s H, 45.01% Cl.
Příklady 2 až 7Examples 2 to 7
Příklady 2 až 7 provedené postupem popsaným v příkladu 1 reprezentující variabilitu reakčních podmínek. Výtěžky 1,1,3-trichlor-3-(p-metylfenyl)propanu byly stanoveny plynově chromatografickou analýzou.Examples 2 to 7 performed according to the procedure described in Example 1 representing the variability of the reaction conditions. The yields of 1,1,3-trichloro-3- (p-methylphenyl) propane were determined by gas chromatographic analysis.
CS 274 226 BlCS 274 226 Bl
A = p-metylstyren, B= chloroform, C= chlorid měďný, D= aminA = p-methylstyrene, B = chloroform, C = cuprous chloride, D = amine
Příklad 8Example 8
Směs 1,4 g (0,01 mol) p-chlorstyrenu, 6 g (0,05 mol) cloroformu, 0,03 g (0,3 mmol) chloridu měďného a 0,15 g (2 mmol) 1-butylaminu se zahřívá v zatavené skleněné ampuli za magnetického míchání v atmosféře dusíku při 90 °C po dobu 6 h. Vzniklý 1,1,3-trichlor-3-(p-chlorfenyl)propan o t.v. 88 °C/50 Pa se izoluje destilací za sníženého tlaku s chromatografickým výtěžkem 81A mixture of 1.4 g (0.01 mol) p-chlorostyrene, 6 g (0.05 mol) cloroform, 0.03 g (0.3 mmol) copper (I) chloride and 0.15 g (2 mmol) 1-butylamine was added. Heat in a sealed glass vial with magnetic stirring under nitrogen atmosphere at 90 ° C for 6 h. The resulting 1,1,3-trichloro-3- (p-chlorophenyl) propane 88 ° C / 50 Pa is isolated by distillation under reduced pressure with a chromatographic yield of 81
Pro C9H?C14 (257,98) vypočteno: 41,89 % C, 3,10 ‘t H, 55,01 % Cl: nalezeno: 42,01 % C, 3,02 % H, 55,12 \ Cl.For C 9 H ? C1 4 (257.98) calculated: 41.89% C, 3.10 t of H, Cl 55.01% Found: 42.01% C, 3.02% H, 55.12 \ Cl.
Příklad 9Example 9
Směs 1,2 g (0,01 mol) p-fluorstyrenu, 6 g (0,05 mol) chloroformu, 0,03 g (0,3 mmol) chloridu měďného a 0,15 g (2 mmol) 1-butylaminu se zahřívá v zatavené skleněné ampuli za magnetického míchání v atmosféře dusíku při 90 °C po dobu 6 h. Vzniklý 1,1,3-trichlor-3-(p-fluorfenyl)propan o t.v. 78 °C/40 Pa se izoluje destilací za sníženého tlaku s chromatografickým výtěžkem 75 %.A mixture of 1.2 g (0.01 mol) of p-fluorostyrene, 6 g (0.05 mol) of chloroform, 0.03 g (0.3 mmol) of copper (I) chloride and 0.15 g (2 mmol) of 1-butylamine was added. Heat in a sealed glass vial with magnetic stirring under nitrogen atmosphere at 90 ° C for 6 h. The 1,1,3-trichloro-3- (p-fluorophenyl) propane formed 78 ° C / 40 Pa was isolated by distillation under reduced pressure with a chromatographic yield of 75%.
Pro C9H9C13F (241,52) vypočteno: 44,70 C, 3,31 % H, 44,12 % Cl, 7,86 \ F; nalezeno: 44,56 C, 3,20 % H, 44,62 \ Cl, 7,91 \ F.For C 9 H 9 Cl 3 F (241.52) calculated: 44.70 C, 3.31% H, 44.12% Cl, 7.86 ° F; found: 44.56 C, 3.20% H, 44.62 \ Cl, 7.91 \ F.
Příklad 10Example 10
Směs 1,5 g (0,01 mol) p-nitrostyrenu, 11,9 (0,1 mol) chloroformu, 0,05 g (0,5 mmol) chloridu měďného a 0,22 g (3 mmol) 1-butylaminu se zahřívá v zatavené skleněné ampuli za magnetického míchání v atmosféře dusíku při 90 °C po dobu 10 h. Vzniklý 1,1,3-trichlor-3-(p-nitrofenyl)propan o t.v. 105 °C/13 Pa se izoluje destilací za sníženého tlaku s chromatografickým výtěžkem 69 %.A mixture of 1.5 g (0.01 mol) p-nitrostyrene, 11.9 (0.1 mol) chloroform, 0.05 g (0.5 mmol) copper (I) chloride and 0.22 g (3 mmol) 1-butylamine is heated in a sealed glass vial with magnetic stirring under nitrogen at 90 ° C for 10 h. The resulting 1,1,3-trichloro-3- (p-nitrophenyl) propane is formed. 105 ° C / 13 Pa was isolated by distillation under reduced pressure with a chromatographic yield of 69%.
Pro C9H9C13NO2 (268,53) vypočteno: 40,34 h C, 2,98 H, 39,63 % Cl, 5,23 ‘-í N; nalezeno: 39,96 % C, 2,84 % H, 39,58 % Cl, 5,41 % N.For C 9 H 9 Cl 3 NO 2 (268.53) calculated: 40.34 H C, 2.98 H, 39.63% Cl, 5.23'N; Found: C 39.96, H 2.84, Cl 39.58, N 5.41.
Příklad 11Example 11
Směs 1,4 g (0,01 mol) m-chlorstyrenu, 6 g (0,05 mol) chloroformu, 0,03 g (0,3 mmol) chloridu měďného a 0,15 g (2 mmol) 1-butylaminu se zahřívá v zatavené skleněné ampuli za magnetického míchání v atmosféře dusíku při 90 °C po dobu 6 h. Vzniklý 1,1,3-trichlor-3(m-chlorfenyl)propan o t.v. 88 °C/50 Pa se izoluje destilací za sníženého tlaku s chromatografickým výtěžkem 76 \.A mixture of 1.4 g (0.01 mol) of m-chlorostyrene, 6 g (0.05 mol) of chloroform, 0.03 g (0.3 mmol) of copper (I) chloride and 0.15 g (2 mmol) of 1-butylamine was added. Heat in a sealed glass vial with magnetic stirring under nitrogen atmosphere at 90 ° C for 6 h. The resulting 1,1,3-trichloro-3 (m-chlorophenyl) propane is formed. 88 ° C / 50 Pa is isolated by distillation under reduced pressure with a chromatographic yield of 76%.
Pro C9HgCl4 (257,98) vypočteno: 41,89 '-i C, 3,10 % H, 55,01 % Cl; nalezeno: 41,52 % C,For C 9 H 4 Cl g (257.98) calculated: 41.89 '-i C, 3.10% H, 55.01% Cl; found: 41.52% C,
3,02 \ H, 55,49 \ Cl.3.02, H, 55.49, Cl.
CS 274 226 81CS 274 226 81
Příklad 12Example 12
Směs 1,5 g (0,01 mol) m-nitrostyrenu, 11,9 g (0,1 mol) chloroformu, 0,05 g (0,5 mmol) chloridu měďného a 0,22 g (3 mmol) 1-butylaminu se zahřívá v zatavené skleněné ampuli za magnetického míchání v atmosféře dusíku při 90 °C po dobu 10 H. Vzniklý 1,1,3-trichlor-3-(m-nitrofenyl)propan o t.v. 105 °C/13 Pa se izoluje destilací za sníženého tlaku s chromatografickým výtěžkem 55 %.A mixture of 1.5 g (0.01 mol) m-nitrostyrene, 11.9 g (0.1 mol) chloroform, 0.05 g (0.5 mmol) copper (I) chloride and 0.22 g (3 mmol) 1- The butylamine is heated in a sealed glass vial with magnetic stirring at 90 ° C for 10 H under nitrogen. The resulting 1,1,3-trichloro-3- (m-nitrophenyl) propane is formed. 105 ° C / 13 Pa was isolated by distillation under reduced pressure with a chromatographic yield of 55%.
Pro C9H9C13NO2 (268,53) vypočteno: 40,34 % C, 2,98 % H, 39,63 h Cl, 5,23 N; nalezeno: 39,98 h C, 3,01 h H, 40,05 % Cl, 5,34 % N.For C 9 H 9 Cl 3 NO 2 (268.53) calculated: 40.34% C, 2.98% H, 39.63 h Cl, 5.23 N; Found: C, 39.98; H, 3.01; Cl, 40.05; N, 5.34.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS719788A CS274226B1 (en) | 1988-11-01 | 1988-11-01 | Substituted 1,1,3-trichloro-3-phenylpropanes and method of their preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS719788A CS274226B1 (en) | 1988-11-01 | 1988-11-01 | Substituted 1,1,3-trichloro-3-phenylpropanes and method of their preparation |
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| Publication Number | Publication Date |
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| CS719788A1 CS719788A1 (en) | 1990-09-12 |
| CS274226B1 true CS274226B1 (en) | 1991-04-11 |
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| CS719788A CS274226B1 (en) | 1988-11-01 | 1988-11-01 | Substituted 1,1,3-trichloro-3-phenylpropanes and method of their preparation |
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| Country | Link |
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| CS (1) | CS274226B1 (en) |
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