IL44599A - Tetrasubstituted alpha-halocyclobutanone derivatives and their preparation - Google Patents
Tetrasubstituted alpha-halocyclobutanone derivatives and their preparationInfo
- Publication number
- IL44599A IL44599A IL44599A IL4459974A IL44599A IL 44599 A IL44599 A IL 44599A IL 44599 A IL44599 A IL 44599A IL 4459974 A IL4459974 A IL 4459974A IL 44599 A IL44599 A IL 44599A
- Authority
- IL
- Israel
- Prior art keywords
- group
- carbon atoms
- acid
- alkyl group
- chlorine
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- -1 polymethylene group Polymers 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 238000007157 ring contraction reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/12—Saturated polycyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
- C07C49/467—Saturated compounds containing a keto group being part of a ring containing halogen polycyclic
- C07C49/473—Saturated compounds containing a keto group being part of a ring containing halogen polycyclic a keto group being part of a condensed ring system
- C07C49/477—Saturated compounds containing a keto group being part of a ring containing halogen polycyclic a keto group being part of a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
derivatives and their preparation SHELL RESEARCH 42689 This invention relates to novel halocyclobutanones which are of interest as chemical intermediates for the preparation of cyclopropane carboxylic Accordingly the present invention provides halocyclobutanones of general formula wherein and each represents an alkyl group of carbon for example represents an alkyl group of carbon for example methyl and represents an alkyl group of carbon for example methyl or an alkenyl group of up to 6 carbon for example a phenyl or and together form a polymethylene group of up to 6 carbon for example trimethylene or and represents a hydrogen atom or an alkyl of for example and Hal represents a chlorine or bromine The halocyclobutanones of the invention may be prepared by a prooess which oomprises treating the corresponding cyolobutanone of a souroe of chlorine or preferably in a suitable organic solvent such as The chlorine or bromine source may be either the free element a procedure preferred bromine to be or a oompound capable of generating chlorine or bromine in a chemically active form under the reaction When it is desired to introduoe a chlorine atom the use of a generator such as sulphuryl is As mentioned above the halocyclobutanones of the invention are of interest as intermediates for the preparation of oyolopropane carboxylic acids of When the halocyclobutanones of formula I are heated in the presence of a suitably an inorganio base such as aqueous sodium they undergo a ring contraction to give a salt of the acid of formula The free aoid may be liberated by treatment of the salt with a suitable for example an aqueous mineral acid such as aqueous hydrochloric Certain esters of the cyclopropane acids of formula III are of interest as especially certain esters of cyclopropane oarboxylic The invention is illustrated further in the following Example 1 Preparation of was dissolved in ohloroform and to this solution was added dropwise a solution of bromine in chloroform After the addition the solvent was removed under reduoed pressure and the residue was distilled to give the required product as a colourless liquid at n Example 2 Preparation of was dissolved in chloroform and to this solution was added dropwise a solution of bromine in ohloroform was oomplete after the addition of each After the addition the solvent was removed under reduoed pressure to yield the desired product as a pale yellow liquid 20 Example 3 Preparation of was dissolved in ohloroform and sulphury chloride After allowing the mixture to stand for Z hours at the solvent was removed under reduoed pressure to yield the desired product as a pale orange liquid 1 Example Following a similar procedure to that described in Examples 1 to the following oompounds were also yellow 1 2 3 yellow yellow yellow 5 1 lobutanone 1 Example 5 Preparation of oarboxyllo prepared as in Example was added to a saturated solution of sodium carbonate and the mixture was heated under reflux for The cooled solution was then extracted with hexane and the aqueous phase was acidified with oonoentrated hydrochloric The white precipitate formed was filtered off and recrystallised from a methanol mixture to give the required produot pt Analysis Calculated for 02 C H Pound C H Example 6 Preparation of acid prepared as in Example was dissolved in methanol and the solution added to aqueous sodium carbonate solution The mixture was then heated under reflux with vigorous stirring for After the solution was extraoted with hexane and the aqueous phase acidified with concentrated hydroohloric The resulting pale yellow precipitate was filtered off and from mixture to the desired product Analysis Calculated for H Pound C H Example 7 Following a similar procedure to that described in Examples 5 and 6 the following oompounds were also acid Analysis Calculated for C H Found C H oarboxylic acid point Analysis Calculated 02 C H Pound C c acid ll Analysis Calculated for 02 C Pound C H acid Analysis Calculated for Cg C H Pound C H sarboxylic acid Analysis Calculated for C H Pound C H acid insufficientOCRQuality
Claims (12)
1. Halocyclobutanones of general formulax- wherein R^ and R≥ each represents an alkyl group of 1 to 6 carbon atoms; represents an alkyl group of 1 to 6 carbon atoms and R^ represents-an-alkyl group o -lH;o-6-earbon -atom8,—an-alkenyl^ - group of up to 6 carbon atoms, or a phenyl group, or R^ and ^ together form a polymethylene group of up to 6 carbon atoms; and ^ represents a hydrogen atom or an alkyl group of 1 to 6 carbon atoms; and Hal represents a chlorine or bromine atom.
2. Compounds as claimed in claim 1 'wherein R1 and Rg each represents a methyl group; R^ represents a methyl group and R^ represents a methyl, propyl, butenyl or phenyl group, or R^ and ^ together represent an ethylene, trimethylene or pentamethylene group; and R^ represents a hydrogen atom or a methyl group.
3. Compounds as claimed in claim 1 wherein R^ represents an alkyl group of 1 to 6 carbon atoms or a phenyl group.
4. A process for the preparation of halocyclobutanones as defined in claim 1 which comprises treating the corre onding cyclobutanone of formula I - 44599/2 8 - wherein R1 , Rg» ^, R^ and R^ have the meanings defined in claim 1, with a source of chlorine or "bromine.
5. Process as claimed in claim 4 wherein the cyclobutanone of formula II is reacted with a compound capable of generating chlorine or bromine in a chemically active form under the reaction conditions.
6. Process as claimed in claim 5 wherein the chlorine generating compound is sulphury! chloride.
7. Process as claimed in claim 4, 5 or 6 wherein the reaction is carried out in the presence of an organic solvent.
8. Halocyclobutanones when prepared by a process as claimed in any one of claims 5 to 7.
9. « Procese for the preparation of cyclopropane_carboxylic acids of the formula:- wherein R„ , R_, R,f R. and Rc are as defined in claim 1, which comprises heating a halocyclobutanone as claimed in any of claims 1 to 3 or 8 in the presence of a base, and liberating the resultant acid salt by reaction with a suitable acid. 44599/2 - 9
10. Process as claimed in claim 9 wherein the base is an in-organic base and the acid is an aqueous mineral acid.
11. Process as claimed in claim 10 wherein the base is aqueous sodium carbonate and the acid is aqueous hydrochloric acid.
12. Cyclopropane carboxylic acids of formula III as defined in claim 9 when prepared by a process as claimed in any one of claims 9 to 11. HE:dn
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1819573A GB1437832A (en) | 1973-04-16 | 1973-04-16 | Halocyclobutanones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44599A0 IL44599A0 (en) | 1974-06-30 |
| IL44599A true IL44599A (en) | 1977-02-28 |
Family
ID=10108286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44599A IL44599A (en) | 1973-04-16 | 1974-04-10 | Tetrasubstituted alpha-halocyclobutanone derivatives and their preparation |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5810371B2 (en) |
| BE (1) | BE813520A (en) |
| BR (1) | BR7402924D0 (en) |
| CH (1) | CH589584A5 (en) |
| DD (1) | DD113347A5 (en) |
| DE (1) | DE2417615A1 (en) |
| FR (1) | FR2225407B1 (en) |
| GB (1) | GB1437832A (en) |
| HU (1) | HU168443B (en) |
| IL (1) | IL44599A (en) |
| IT (1) | IT1005785B (en) |
| NL (1) | NL189756C (en) |
| SU (1) | SU554809A3 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1051454A (en) * | 1975-05-21 | 1979-03-27 | Marinus J. Van Den Brink | Process for the preparation of cyclobutanones |
| GB1571581A (en) * | 1976-01-06 | 1980-07-16 | Shell Int Research | Process for the preparation of 2-halocyclobutanones and cyclopropane carbolic acids derived therefrom |
| DE2638356A1 (en) * | 1976-08-26 | 1978-03-02 | Bayer Ag | METHOD FOR PRODUCING VINYL-SUBSTITUTED CYCLOPROPANCARBONIC ACID ESTERS |
| FI780931A7 (en) * | 1977-03-31 | 1978-10-01 | Ciba Geigy | 2-(2'2'-DIHALOGENVINYL)-OCH 2-(2'2'2'-TRIHALOGENETYL)-CYCLOBUTANONER FOERFARANDE FOER DERAS FRAMSTAELLNING OCH DERAS ANVAENDNING |
| FI780930A7 (en) * | 1977-03-31 | 1978-10-01 | Ciba Geigy Ag | FOERFARANDE FOER FRAMSTAELLNING AV 2-(2'2'2'-TRIHALOGENETYL)-4-HALOGENCYCLOBUTAN-1-ONER DE MEDELST FOERFARANDE FRAMSTAELLDA PRODUKTERNA OCH DERAS ANVAENDNING SAMT DE FOER DERAS FRAMSTAELLNING ANVAENDA MELLANPRODUKTERNA |
| DE3220730A1 (en) * | 1982-06-02 | 1983-12-08 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF 2,2-DIMETHYL-3-ARYL-CYCLOPROPANE-CARBONIC ACIDS (CARBONIC ACID ESTERS), NEW INTERMEDIATE PRODUCTS THEREFOR AND METHOD FOR THE PRODUCTION THEREOF |
| US6160134A (en) * | 1997-12-24 | 2000-12-12 | Bristol-Myers Squibb Co. | Process for preparing chiral cyclopropane carboxylic acids and acyl guanidines |
-
1973
- 1973-04-16 GB GB1819573A patent/GB1437832A/en not_active Expired
-
1974
- 1974-04-05 IT IT42674/74A patent/IT1005785B/en active
- 1974-04-10 DE DE2417615A patent/DE2417615A1/en not_active Withdrawn
- 1974-04-10 CH CH502474A patent/CH589584A5/xx not_active IP Right Cessation
- 1974-04-10 FR FR7412630A patent/FR2225407B1/fr not_active Expired
- 1974-04-10 JP JP49040129A patent/JPS5810371B2/en not_active Expired
- 1974-04-10 HU HUSE1720A patent/HU168443B/hu not_active IP Right Cessation
- 1974-04-10 SU SU2014993A patent/SU554809A3/en active
- 1974-04-10 BE BE1005867A patent/BE813520A/en not_active IP Right Cessation
- 1974-04-10 IL IL44599A patent/IL44599A/en unknown
- 1974-04-10 BR BR2924/74A patent/BR7402924D0/en unknown
- 1974-04-10 DD DD177810A patent/DD113347A5/xx unknown
- 1974-04-11 NL NLAANVRAGE7404949,A patent/NL189756C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2225407B1 (en) | 1976-06-25 |
| IT1005785B (en) | 1976-09-30 |
| BE813520A (en) | 1974-10-10 |
| FR2225407A1 (en) | 1974-11-08 |
| JPS5810371B2 (en) | 1983-02-25 |
| IL44599A0 (en) | 1974-06-30 |
| HU168443B (en) | 1976-04-28 |
| CH589584A5 (en) | 1977-07-15 |
| NL7404949A (en) | 1974-10-18 |
| GB1437832A (en) | 1976-06-03 |
| DD113347A5 (en) | 1975-06-05 |
| BR7402924D0 (en) | 1974-11-19 |
| SU554809A3 (en) | 1977-04-15 |
| NL189756C (en) | 1993-07-16 |
| DE2417615A1 (en) | 1974-11-07 |
| JPS5030846A (en) | 1975-03-27 |
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