DE1618668A1 - Process for the preparation of phosphabenzenes - Google Patents
Process for the preparation of phosphabenzenesInfo
- Publication number
- DE1618668A1 DE1618668A1 DE19671618668 DE1618668A DE1618668A1 DE 1618668 A1 DE1618668 A1 DE 1618668A1 DE 19671618668 DE19671618668 DE 19671618668 DE 1618668 A DE1618668 A DE 1618668A DE 1618668 A1 DE1618668 A1 DE 1618668A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- mmol
- yield
- preparation
- phosphabenzenes
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- ZXKWYKJATBZOOE-UHFFFAOYSA-N tetrahydroxy(methyl)-$l^{5}-phosphane Chemical compound CP(O)(O)(O)O ZXKWYKJATBZOOE-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 alconyl Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SPVWSVYJPGRPFL-UHFFFAOYSA-N 2,4,6-triphenylphosphinine Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=PC(C=2C=CC=CC=2)=C1 SPVWSVYJPGRPFL-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- UNQNIRQQBJCMQR-UHFFFAOYSA-N phosphorine Chemical compound C1=CC=PC=C1 UNQNIRQQBJCMQR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Verfahren zur Herstellung von Phosphabenzolen Es ist bisher nicht
gelunge, Phosphorverbindungen mit dem Grundgerüst des Phosphablenzols aufzubauen:
Es wurde nun gefunden, daß man gubstituierte Phosphabenzole tier Formel
erthält, wenn man substituierte Pyryliumsalze der Formel
mit Trishydroxymethyl-phosphin, tetrahydroxymethyl-phospha nium-chlorid oder Tetrahydroxymethyl-phosphonium-hydroxyd
umsetst
In den Formeln bedeuten R1 bis R5 Alkyl-, Alkonyl0, Aralkyl-,
Aryl- oder heter?cyclische Resto, die durch belietige Cruppen aubstitujort sein
könne. Es vorsteht sich, daß dabei solche Gruppen auageschlossen sind, die selbst
mit den Tris-hydroxymethylphosphin in Reaktion treten. Insbesondere kommen 4 nfrase
:
Als Ausgangsstoffe für das Verfahren eignen sich Pyryliumsalze der Formel II, in denen X? beispielsweise BF4 -, C104 -, J - bedeuton. Grundsätzlich kommen für X- sämtliche Anionon infrage, die in dor Lage sind, stabile Pyryliumsalze cu bilden. Als Lösungsmittel werd on vorzugsweise Pyridin und alkylsubstituierte Pyridine verwondet. Man arbeitet unter Sauerstoffausschluß bei der Siedetemperatur des Lösungsmittels.Pyrylium salts are suitable as starting materials for the process Formula II in which X? for example BF4 -, C104 -, J - meaning. Basically come for X- all anion in question, which are in the position, stable pyrylium salts cu form. The solvents used are preferably pyridine and alkyl-substituted ones Pyridine bonded. One works with exclusion of oxygen at the boiling point of the solvent.
Die Substanzen sind schwer löslich in Wasser, Methanol, Äthanol, Petroläther, gut löslich in Chlorotor, Benzol und anderen aromtischen Lösungsmitteln. Im Gegensatz zu dem normalen Verhalten von Phosphinen sind sie skohl im kristallinen Zustand wie in Lösung nicht utoxydabel, reagieron nicht mit Schwefel und sind nicht alkylierbar durcli Alkylhaloenide oder triäthyl- bew. Timethyloxoniumfluorborat. Die Verbindungen eignen sich ? als Zwischenprodukte für di. Herstellung pharmazeutisch aktiver Substanzen.The substances are sparingly soluble in water, methanol, ethanol, petroleum ether, easily soluble in chlorotor, benzene and other aromatic solvents. In contrast in addition to the normal behavior of phosphines, they are skohl in the crystalline state as in solution they are not oxidizable, do not react with sulfur and cannot be alkylated by alkyl halides or triethyl, or timethyloxonium fluoroborate. The connections are suitable? as intermediates for di. Manufacture of pharmaceutically active substances.
Beispiel 1 2.4.6-Triphenylphosphabenzol Eine Lösung von 2.0 g (5mMmol) 2.4.6-Triphenylpyryliumflueroborat und 1.0 g (7.5mMol) Trishydroxymethylphosphin in 5.0 ml absolutem Pyridin wird unter Reinetickstoff 3 Stunden unter Rückfluß zum Sieden erhitzt. Bereits nach wenigen Minuten beginnt eine kräftige Entwicklung von Formaldehyd, der sich überwiegen als Polymeres im Rückflu#kühler niederschlägt. Example 1 2.4.6-Triphenylphosphabenzene A solution of 2.0 g (5mMmol) 2.4.6-triphenylpyrylium fluoroborate and 1.0 g (7.5 mmol) trishydroxymethylphosphine in 5.0 ml of absolute pyridine is refluxed under pure nitrogen for 3 hours Boiling heated. After a few minutes a strong development of Formaldehyde, which is mainly deposited as a polymer in the reflux cooler.
Aus der erkalteten Reaktionslösung kristallisiert das 2. 4. 6-Triphenylphosphabenzol 1 in schwachgelben Nadeln. Durch vorsichtigc Zugabe von Wasser wird die Abscheidung vervollständigt. Die Ausbeute beträgt 25 - 30 % d. Th. Umkristallisation au chloroform/Äthanol liefert schwach gelbe Nadeln vom Fp. 172 - 173°C. The 2, 4, 6-triphenylphosphabenzene crystallizes from the cooled reaction solution 1 in pale yellow needles. By carefully adding water, the deposit is made completed. The yield is 25-30% of theory. Th. Recrystallization from chloroform / ethanol yields pale yellow needles with a melting point of 172-173 ° C.
Tetrhydroxymethyl-phosphonium-chlorid reagiert bei analoger Reaktionsführung ebenfalls zum 2.4.6-Triphenyl-phosphabenzol. Aufarbeitung wie oben angegeben, Ausbeute 18 % d. na.Tetrhydroxymethyl phosphonium chloride reacts if the reaction is carried out in a similar manner also to 2.4.6-triphenyl-phosphabenzene. Work-up as indicated above, yield 18% d. n / A.
Beispiel 2 2.3.4.6-Tetraphenylphosphabenzol 4.7 g 2.3.4.6-Totraphonylpyryliumfluoroborat (10 - mMol) und 2.2 g Trishydroxymethylphosphin werden in 10 ml abs. Example 2 2.3.4.6-Tetraphenylphosphabenzene 4.7 g 2.3.4.6-Totraphonylpyrylium fluoroborate (10 - mmol) and 2.2 g of trishydroxymethylphosphine in 10 ml of abs.
Pyridin 12 Stunden unter reinstickstoff n Rückfluß erhitzt. Hierauf wird das Lösungsmittel im Vakuum abdestilliert, der Rückstand mit Benzol extrahiert und die Benzolphase ao Al2O3 chromntographiert. Das 2.3.4.6-Tetraphenylphosphabenzol wird aus Eisessig umkristallisiert. Pyridine was refluxed for 12 hours under pure nitrogen. On that the solvent is distilled off in vacuo and the residue is extracted with benzene and the benzene phase ao Al2O3 chromntographed. The 2.3.4.6-tetraphenylphosphabenzene is recrystallized from glacial acetic acid.
Ausbeute 10 %, Fp. 209 - 2100C. Yield 10%, m.p. 209-2100C.
Beispiel 3 2.3.4.5.6-Pentaphenylphosphabenzol 7.0 g 2.3.4.5.6-Pontaphenyl-pyrylium-perchlorat (12.7 mMol) und 2.8 g trishydroxymethylphosphin in 14 ml abs. Pyridin werden unter Reinstickstoff 4 Stunden am Rückfluß erhitzt. Example 3 2.3.4.5.6-Pentaphenylphosphabenzene 7.0 g 2.3.4.5.6-Pontaphenyl-pyrylium-perchlorate (12.7 mmol) and 2.8 g of trishydroxymethylphosphine in 14 ml of abs. Pyridine will be taking Pure nitrogen heated under reflux for 4 hours.
Die Aufarbeitung erfolgt wie in Beispiel 2. Das Produkt schmilst bei 253 - 254°C, Ausbeute 17 %. The work-up is carried out as in Example 2. The product schmilst at 253-254 ° C, yield 17%.
Beisniel 4 2.6-Di-(p. -methoxyphenyl)-4-phenyl-phosphabenzol 4., g 2.6-Di-(p. methoxyphenyl)-4-phenyl-pyryliumperchlerat t 10 mMol) und 2.2 g trishydroxymethylphosphin in t w abs. Pyridin worden 3 Stunden im Rückflu# erhitst. Die aufarbeitung erfolgt wie in Beispiel a. Das Predukt schmilst bei 136 - 137°C (aus Eisessig).Example 4 2.6-Di- (p. -Methoxyphenyl) -4-phenyl-phosphabenzene 4., g 2.6-di- (p. Methoxyphenyl) -4-phenyl-pyrylium perchlerate t 10 mmol) and 2.2 g trishydroxymethylphosphine in t w abs. Pyridine was refluxed for 3 hours. The processing takes place as in example a. The preduct melts at 136 - 137 ° C (from glacial acetic acid).
Ausbeute 34 %. Yield 34%.
Beispiel 3 2.6-Di-(p. -chlorphenyl)-4-phenyl-phosphabenzol 2.5 g 2.6-Di-(p. chlorphenyl)-4-phenyl-pyryliumfluoroborat (5.4 mMol) und .4 g trishydroxymethylphosphin in 5 ml abs.Example 3 2.6-di- (p. -Chlorophenyl) -4-phenyl-phosphabenzene 2.5 g of 2.6-di- (p. chlorophenyl) -4-phenyl-pyrylium fluoroborate (5.4 mmol) and .4 g trishydroxymethylphosphine in 5 ml abs.
Pyridin werden 5 Stunden unter Reinstickkstoff am Rückflu# erhitzt. Die aufarbeitung erfelgt wie in Beispiel 2.Fp 189-191°C.Pyridine is refluxed for 5 hours under pure nitrogen. Working up is as in Example 2, mp 189-191 ° C.
(aus Eisessig), Ausbeute 15 X d. Th.(from glacial acetic acid), yield 15 X d. Th.
Beispiel 6 2.6-Di-(p-tolyl)-4-phenyl-phosphabenzol: 6.4 g (15 mMol) 2.6-Di-(p-tolyl)-4-phenyl-pyrylium-fluoroborat und 3.7 g (30 mMol) Trishydroxymethyl-phosphin werden in 20 mi abs. Pyridin 3 Stunden unter Rückfu# zum Sieden erhizt.Example 6 2.6-Di- (p-tolyl) -4-phenyl-phosphabenzene: 6.4 g (15 mmol) 2.6-Di- (p-tolyl) -4-phenyl-pyrylium-fluoroborate and 3.7 g (30 mmol) trishydroxymethyl-phosphine are in 20 mi abs. Pyridine heated to boiling under reflux for 3 hours.
Die Weitere Aufarbeitung erfolgt wie unter Beispiel 2 angegeben.Further work-up takes place as indicated in Example 2.
Fp 133 - 134°C (aus wenig Eisessig), Ausbeute 14 3' d. Th.Mp 133-134 ° C (from a little glacial acetic acid), yield 14 3 'd. Th.
Beispiel 7 2.4.6-Tri-(p-methoxyphenyl)-phosphabenzol : 4.8 mg (lOmMbl) 2.4.6-Tri-(p-methoxyphenyl)-pyrliumperchlorat und 2.5 g (20 mMol) Tishydroxymethyl-phosphin in 20 ml abs. Pyridin werden 3 Stunden unter Rückfluß zum Sieden orhitzt. Die erkaltete Reaktionaslöaung wird vorsichtig bis zur beginnenden Trübung mit Wasser versetzt. Das Phosphabenzol kristallisiert in der Kälte direkt aus, Fp 105 - 1060C (aus Eisessig), Ausbeute 33 % d. Th.Example 7 2.4.6-Tri- (p-methoxyphenyl) -phosphabenzene: 4.8 mg (10mMbl) 2.4.6-tri- (p-methoxyphenyl) -pyrlium perchlorate and 2.5 g (20 mmol) tishydroxymethyl-phosphine in 20 ml abs. Pyridine is refluxed for 3 hours. The cooled down Reaction gas solution is carefully mixed with water until the onset of turbidity. The phosphabenzene crystallizes out directly in the cold, mp 105-1060C (from glacial acetic acid), Yield 33% of theory Th.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0073237 | 1967-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618668A1 true DE1618668A1 (en) | 1971-02-25 |
Family
ID=7314918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618668 Pending DE1618668A1 (en) | 1967-03-18 | 1967-03-18 | Process for the preparation of phosphabenzenes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1618668A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000055164A1 (en) * | 1999-03-17 | 2000-09-21 | Basf Aktiengesellschaft | Phosphabenzene compounds and their use as ligands for hydroformylation catalysts |
| US6252117B1 (en) | 1999-03-17 | 2001-06-26 | Basf Aktiengesellschaft | Preparation of phosphabenzene compounds |
| US6255532B1 (en) | 1997-09-30 | 2001-07-03 | Basf Aktiengesellschaft | Method for producing phosphabenzene compounds |
-
1967
- 1967-03-18 DE DE19671618668 patent/DE1618668A1/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255532B1 (en) | 1997-09-30 | 2001-07-03 | Basf Aktiengesellschaft | Method for producing phosphabenzene compounds |
| WO2000055164A1 (en) * | 1999-03-17 | 2000-09-21 | Basf Aktiengesellschaft | Phosphabenzene compounds and their use as ligands for hydroformylation catalysts |
| US6252117B1 (en) | 1999-03-17 | 2001-06-26 | Basf Aktiengesellschaft | Preparation of phosphabenzene compounds |
| US6509505B1 (en) | 1999-03-17 | 2003-01-21 | Basf Aktiengesellschaft | Phosphabenzene compounds and their use in hydroformylation |
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