Chemistry:Tris(2,4,6-trimethoxyphenyl)phosphine
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| IUPAC name
Tris(2,4,6-trimethoxyphenyl)phosphane
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Other names
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C27H33O9P | |
| Molar mass | 532.526 g·mol−1 |
| Melting point | 79–81 °C (174–178 °F; 352–354 K) |
| Boiling point | 360 or 377 °C (680 or 711 °F; 633 or 650 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) is a large triaryl organophosphine whose strong Lewis-basic properties make it useful as an organocatalyst for several types of chemical reactions.
It removes the trimethylsilyl group from ketene silyl acetals (the enol ether of esters) to give enolates that can then act as strong nucleophiles. It thus serves as a catalyst for Mukaiyama aldol reactions[2] and group-transfer chain-growth polymerization reactions.[3]
As a Brønsted base, it can deprotonate various alcohols, giving nucleophilic alkoxides that can undergo Michael addition reactions.[4]
It can act as a Michael nucleophile itself to catalyze Baylis–Hillman reactions.[5]
References
- ↑ Various chemical catalogs give one or the other value (see ChemSpider for collected list)
- ↑ Matsukawa, Satoru; Okano, Naoko; Imamoto, Tsuneo (2000). "Phosphine catalyzed aldol reaction between ketene silyl acetals and aldehydes: nucleophilic O–Si and C–Si bond cleavage by phosphines". Tetrahedron Letters 41 (1): 103–107. doi:10.1016/S0040-4039(99)02014-6.
- ↑ Fevre, Maréva; Vignolle, Joan; Heroguez, Valérie; Taton, Daniel (2012). "Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) as Potent Organocatalyst for Group Transfer Polymerization of Alkyl (Meth)acrylates". Macromolecules 45 (19): 7711–7718. doi:10.1021/ma301412z. Bibcode: 2012MaMol..45.7711F.
- ↑ Fischer, Susanne M.; Kaschnitz, Petra; Slugov, Christian (2022). "Tris(2,4,6-trimethoxyphenyl)phosphine – a Lewis base able to compete with phosphazene bases in catalysing oxa-Michael reactions". Catalysis Science & Technology 12 (20): 6204–6212. doi:10.1039/D2CY01335E.
- ↑ Trofimov, Alexander; Gevorgyan, Vladimir (2009). "Sila-Morita−Baylis−Hillman Reaction of Arylvinyl Ketones: Overcoming the Dimerization Problem". Organic Letters 11 (1): 253–255. doi:10.1021/ol8026522. PMID 19055398.
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