A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819)
A straightforward high-yield synthesis for the photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphane oxide (16, IRGACURE 819) involves: i) the reaction of phenyldichlorophosphane, PhPCl2, with sodium to give [Na2(P2Ph2)(tmeda)]6 (5); ii) protonation of 5 with tert-butanol to give 1,2-d...
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Swiss Chemical Society
2008-02-01
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| Series: | CHIMIA |
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| Online Access: | https://chimia.ch/chimia/article/view/4427 |
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| author | Hansjörg Grützmacher Peter Murer Jean-Pierre Wolf Souad Boulmaaz Reinhard H. Sommerlade Hartmut Schönberg Timo Ott Daniel Stein Jens Geier Thomas Ulrich |
| author_facet | Hansjörg Grützmacher Peter Murer Jean-Pierre Wolf Souad Boulmaaz Reinhard H. Sommerlade Hartmut Schönberg Timo Ott Daniel Stein Jens Geier Thomas Ulrich |
| author_sort | Hansjörg Grützmacher |
| collection | DOAJ |
| description |
A straightforward high-yield synthesis for the photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphane oxide (16, IRGACURE 819) involves: i) the reaction of phenyldichlorophosphane, PhPCl2, with sodium to give [Na2(P2Ph2)(tmeda)]6
(5); ii) protonation of 5 with tert-butanol to give 1,2-diphenyldiphosphane, PhHP-PHPh (12); iii) reduction of 12 by sodium to yield [Na(PHPh)]x (13); iv) protonation of 13 with tert-butanol to give phenylphosphane PhPH2
(14) in excellent yields; v) reaction of 14 with 2,4,6-trimethylbenzoylchloride (MesCOCl) in presence of the NaOt-Bu formed in steps ii and iv to give bis(2,4,6-trimethylbenzoyl)phenylphosphane 7; vi) oxygenation of 7 with 30% aqueous hydrogen peroxide to
give the final product 16. This reaction can be performed in toluene with about 4 vol-% of tmeda as an activator in a one-pot synthesis without changing the solvent. The structures determined by X-ray diffraction of the unique hexameric aggregate 5 and 16 are reported.
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| first_indexed | 2024-04-13T12:57:31Z |
| format | Article |
| id | doaj.art-38970b9dfc56408a8517742cbec73049 |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-04-13T12:57:31Z |
| publishDate | 2008-02-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-38970b9dfc56408a8517742cbec730492022-12-22T02:46:00ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242008-02-01621-210.2533/chimia.2008.18A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819)Hansjörg GrützmacherPeter MurerJean-Pierre WolfSouad BoulmaazReinhard H. SommerladeHartmut SchönbergTimo OttDaniel SteinJens GeierThomas Ulrich A straightforward high-yield synthesis for the photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphane oxide (16, IRGACURE 819) involves: i) the reaction of phenyldichlorophosphane, PhPCl2, with sodium to give [Na2(P2Ph2)(tmeda)]6 (5); ii) protonation of 5 with tert-butanol to give 1,2-diphenyldiphosphane, PhHP-PHPh (12); iii) reduction of 12 by sodium to yield [Na(PHPh)]x (13); iv) protonation of 13 with tert-butanol to give phenylphosphane PhPH2 (14) in excellent yields; v) reaction of 14 with 2,4,6-trimethylbenzoylchloride (MesCOCl) in presence of the NaOt-Bu formed in steps ii and iv to give bis(2,4,6-trimethylbenzoyl)phenylphosphane 7; vi) oxygenation of 7 with 30% aqueous hydrogen peroxide to give the final product 16. This reaction can be performed in toluene with about 4 vol-% of tmeda as an activator in a one-pot synthesis without changing the solvent. The structures determined by X-ray diffraction of the unique hexameric aggregate 5 and 16 are reported. https://chimia.ch/chimia/article/view/4427AcylphosphanesIon triplesPhosphanesPhosphorusPhotoinitiatorsSodium |
| spellingShingle | Hansjörg Grützmacher Peter Murer Jean-Pierre Wolf Souad Boulmaaz Reinhard H. Sommerlade Hartmut Schönberg Timo Ott Daniel Stein Jens Geier Thomas Ulrich A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819) CHIMIA Acylphosphanes Ion triples Phosphanes Phosphorus Photoinitiators Sodium |
| title | A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819) |
| title_full | A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819) |
| title_fullStr | A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819) |
| title_full_unstemmed | A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819) |
| title_short | A Simple Straightforward Synthesis of Phenylphosphane and the Photoinitiator Bis(mesitoyl)phenylphosphane Oxide (IRGACURE 819) |
| title_sort | simple straightforward synthesis of phenylphosphane and the photoinitiator bis mesitoyl phenylphosphane oxide irgacure 819 |
| topic | Acylphosphanes Ion triples Phosphanes Phosphorus Photoinitiators Sodium |
| url | https://chimia.ch/chimia/article/view/4427 |
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