GB869528A - Vinylic phosphorus compounds - Google Patents
Vinylic phosphorus compoundsInfo
- Publication number
- GB869528A GB869528A GB2208458A GB2208458A GB869528A GB 869528 A GB869528 A GB 869528A GB 2208458 A GB2208458 A GB 2208458A GB 2208458 A GB2208458 A GB 2208458A GB 869528 A GB869528 A GB 869528A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- vinylic
- substituted
- ring
- atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Vinylic phosphorus compounds Chemical class 0.000 title abstract 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000004703 alkoxides Chemical class 0.000 abstract 2
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 125000002348 vinylic group Chemical group 0.000 abstract 2
- HGYMAAGJKNTJPH-UHFFFAOYSA-N (3-fluorophenyl)-bis(3-methylbut-1-enyl)phosphane Chemical compound CC(C=CP(C1=CC(=CC=C1)F)C=CC(C)C)C HGYMAAGJKNTJPH-UHFFFAOYSA-N 0.000 abstract 1
- KZZLUXLJSMHAAS-UHFFFAOYSA-N (5-methylthiophen-2-yl)-bis(pent-1-enyl)phosphane Chemical compound C(=CCCC)P(C=1SC(=CC1)C)C=CCCC KZZLUXLJSMHAAS-UHFFFAOYSA-N 0.000 abstract 1
- ONUSCKAYRIJMBI-UHFFFAOYSA-N C(=C)C(C=C)[P] Chemical compound C(=C)C(C=C)[P] ONUSCKAYRIJMBI-UHFFFAOYSA-N 0.000 abstract 1
- NVHANWCQZOAEQS-UHFFFAOYSA-N C(=C)C(CCCCCCCCCCCCCCCCC[P])C=C Chemical compound C(=C)C(CCCCCCCCCCCCCCCCC[P])C=C NVHANWCQZOAEQS-UHFFFAOYSA-N 0.000 abstract 1
- HKGYYCOOWCMGET-UHFFFAOYSA-N C(=C)C(CCC[P])C=C Chemical compound C(=C)C(CCC[P])C=C HKGYYCOOWCMGET-UHFFFAOYSA-N 0.000 abstract 1
- OCWFRRGENPZEQW-UHFFFAOYSA-N C=C(CC)P(C(=C)CC)C(=C)CC Chemical compound C=C(CC)P(C(=C)CC)C(=C)CC OCWFRRGENPZEQW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 108010021119 Trichosanthin Proteins 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GEKAWPIATFUQJW-UHFFFAOYSA-N bis(ethenyl)-phenylphosphane Chemical compound C=CP(C=C)C1=CC=CC=C1 GEKAWPIATFUQJW-UHFFFAOYSA-N 0.000 abstract 1
- SXCLPGWKQYNJDO-UHFFFAOYSA-N bis(ethenyl)-thiophen-2-ylphosphane Chemical compound C(=C)P(C=1SC=CC1)C=C SXCLPGWKQYNJDO-UHFFFAOYSA-N 0.000 abstract 1
- JPBPKIRCXCPJOG-UHFFFAOYSA-N bis(prop-1-enyl)-quinolin-6-ylphosphane Chemical compound C(=CC)P(C=1C=C2C=CC=NC2=CC1)C=CC JPBPKIRCXCPJOG-UHFFFAOYSA-N 0.000 abstract 1
- SYGDJNLSKMWZEL-UHFFFAOYSA-N but-3-enyl(dichloro)phosphane Chemical compound C(=C)CCP(Cl)Cl SYGDJNLSKMWZEL-UHFFFAOYSA-N 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- HBBXHMISOQXSCN-UHFFFAOYSA-N chloro-bis(ethenyl)phosphane Chemical compound C=CP(Cl)C=C HBBXHMISOQXSCN-UHFFFAOYSA-N 0.000 abstract 1
- QVNUTCARXBTVLP-UHFFFAOYSA-N chloro-ethenyl-phenylphosphane Chemical compound C(=C)P(C1=CC=CC=C1)Cl QVNUTCARXBTVLP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- YOIRZPLWAICUAU-UHFFFAOYSA-N dibenzyl(ethenyl)phosphane Chemical compound C(=C)P(CC1=CC=CC=C1)CC1=CC=CC=C1 YOIRZPLWAICUAU-UHFFFAOYSA-N 0.000 abstract 1
- ZMQFCCAWWXHOFA-UHFFFAOYSA-N dichloro(ethenyl)phosphane Chemical compound ClP(Cl)C=C ZMQFCCAWWXHOFA-UHFFFAOYSA-N 0.000 abstract 1
- YRRRMHBROVXIRL-UHFFFAOYSA-N dichloro(hex-5-enyl)phosphane Chemical compound C(=C)CCCCP(Cl)Cl YRRRMHBROVXIRL-UHFFFAOYSA-N 0.000 abstract 1
- VUBFUMQHMDQUAQ-UHFFFAOYSA-N dichloro(prop-2-enyl)phosphane Chemical compound ClP(Cl)CC=C VUBFUMQHMDQUAQ-UHFFFAOYSA-N 0.000 abstract 1
- VCKGZOHSRDVCPM-UHFFFAOYSA-N ethenyl(diethyl)phosphane Chemical compound CCP(CC)C=C VCKGZOHSRDVCPM-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000002734 organomagnesium group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- TUXDYBILLWMQSC-UHFFFAOYSA-N tri(cyclohexen-1-yl)phosphane Chemical compound C1CCCC(P(C=2CCCCC=2)C=2CCCCC=2)=C1 TUXDYBILLWMQSC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5013—Acyclic unsaturated phosphines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F30/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing boron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Vinylic trivalent phosphorus compounds are prepared by reacting a vinylic magnesium chloride complex of formula ViMgC.hQ wherein Vi is a vinylic radical as hereinafter defined, Q is a substituted or unsubstituted cyclic ether having 5 or 6 atoms in the ring, of which atoms one is oxygen, the other ring atoms being carbon except that a substituted nitrogen atom may replace carbon in the 4 position when the ring has 6 atoms, the ring containing not more than one double bond and at least one ring carbon atom adjacent the oxygen atom being unsubstituted, said ether containing no substituent which reacts with the organo-magnesium chloride complex or with other components of the reaction mixture (Q may be replaced by an ethylene polyether by the method of Specification 826,621) and n is an indeterminate number of the order of 1 to 3 with a trivalent phosphorus halide, alkoxide or aryloxide or with an organo-substituted trivalent phosphorus halide, alkoxide or aryloxide, the organo substituent whereof contains no reactive group. The term "vinylic radical" is defined as of formula: <FORM:0869528/IV (b)/1> wherein R, R1 and R11 represent either hydrogen or a substituted or unsubstituted hydrocarbon radical containing no group reactive under the conditions of the reaction and includes cycloalkenyl radicals, which may be substituted, of formula: <FORM:0869528/IV (b)/2> where a is a whole number greater than 1. An organic solvent which may be the compound Q is usually used. Reaction temperatures are usually between room temperature and the reflux temperature. An inert atmosphere is preferably used. Examples describe the preparation of (1), (2), (23), (24), (25), trivinylphosphorus; (3) divinylbutylphosphorus; (4) divinyloctadecylphosphorus; (5) divinylphenylphosphorus; (6) divinylmethylphosphorus; (7) vinyldiethylphosphorus; (8) viniyldilaurylphosphorus; (9) vinyldibenzylphosphorus; (10) divinylthienylphosphorus; (11) vinylcyclopentamethylenephosphorus; (12) di-(1-propenyl)6-quinolylphosphorus; (13) tri (buten-2-yl)phosphorus; (14) di-(3-methyl-1-butenyl)m-fluorophenylphosphorus; (15) di-(penten-1-yl) 5-methylthienylphosphorus; (16) divinylphosphorus chloride; (17) vinylphosphorus dichloride; (18) vinylphenylphosphorus chloride; (19) vinylbutylphosphorus chloride; (20) vinylethylphosphorus chloride; (21) vinylmethylphosphorus chloride; (22) tris(1-cyclohexenyl)phosphorus. Specification 792,537 also is referred to.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3551/55A GB777158A (en) | 1954-03-01 | 1955-02-07 | Vinylic magnesium chloride complexes and method of making same |
| GB2208458A GB869528A (en) | 1958-07-09 | 1958-07-09 | Vinylic phosphorus compounds |
| GB22086/58A GB878130A (en) | 1954-03-01 | 1958-07-09 | Vinylic aluminium compounds |
| GB22085/58A GB873180A (en) | 1954-03-01 | 1958-07-09 | Process for the preparation of vinyl boron compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2208458A GB869528A (en) | 1958-07-09 | 1958-07-09 | Vinylic phosphorus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB869528A true GB869528A (en) | 1961-05-31 |
Family
ID=10173664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2208458A Expired GB869528A (en) | 1954-03-01 | 1958-07-09 | Vinylic phosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB869528A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201837B (en) * | 1962-07-20 | 1965-09-30 | Carlisle Chemical Works | Process for the preparation of trialkylphosphines |
| US3355439A (en) * | 1963-10-30 | 1967-11-28 | Union Carbide Corp | Polymers of coordination complexes of vinylphosphines and metal salts, and process for preparing same |
-
1958
- 1958-07-09 GB GB2208458A patent/GB869528A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201837B (en) * | 1962-07-20 | 1965-09-30 | Carlisle Chemical Works | Process for the preparation of trialkylphosphines |
| US3355439A (en) * | 1963-10-30 | 1967-11-28 | Union Carbide Corp | Polymers of coordination complexes of vinylphosphines and metal salts, and process for preparing same |
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