New Aspects in Phosphorus Chemistry
(Sprache: Englisch)
Strong non-ionic bases are highly advantageous as stoichiometric reagents and as catalysts in synthetic organic chemistry owing to side reactions that f- quently occur when ionic bases such as LDA or alkali metal alkoxides are employed. A second reason that...
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Strong non-ionic bases are highly advantageous as stoichiometric reagents and as catalysts in synthetic organic chemistry owing to side reactions that f- quently occur when ionic bases such as LDA or alkali metal alkoxides are employed. A second reason that non-ionic bases are frequently more useful in these applications is that such bases are often more soluble in less polar organic solvents,particularly at low temperatures. Thirdly,non-ionic bases can provide reactive naked or tightly associated deprotonated substrate anions that are s- bilized by the relatively large,poorly solvated cations formed by the protonated base. In such cations,extensive positive charge delocalization can occur. Prior to our work on pro-azaphosphatranes of type 1 (Scheme 1),the very strong n- ionic bases utilized for organic transformations were largely confined to the nitrogenous bases shown below (Scheme 2). Scheme 1 Scheme 2 4 J. G. Verkade 2 Uses of Strong Nonionic Nitrogen Bases 2. 1 Amines One of the earliest strong non-ionic bases to make its appearance was Proton Sponge and its derivatives [1] and these systems have been reviewed [2]. More recently Proton Sponge has been used in the palladium-catalyzed arylation of 2,3-dihydrofuran [3], and it also catalyzes Knoevenagel condensations of s- strates possessing activated methylene groups [4]. Recently the synthesis of the macrocyclic tetramine below (Scheme 3) was reported [5]. The encrypted nitrogens are very basic (pK ,24.
Inhaltsverzeichnis zu „New Aspects in Phosphorus Chemistry “
- J.G. Verkade: P(RNCH2CH2)3N: Very Strong Non-ionic Bases Useful in Organic Synthesis- T.P. Kee, T.D. Nixon: The Asymmetric Phospho-Aldol Reaction. Past, Present, and Future
- M. Yoshifuji, S. Ito: Chemistry of Phosphanylidene Carbenoids
- R. Streubel: Transient Nitrilium Phosphanylid Complexes: New Versatile Building Blocks in Phosphorus Chemistry
- J.-P. Majoral, A.-M. Caminade: What To Do With Phosphorus in Dendrimer Chemistry
- M. Mikolajczyk, P. Balczewski: Phosphonate Chemistry and Reagents in the Synthesis of Biologically Active and Natural Products
- H. Heydt: The Fascinating Chemistry of Triphosphabenzenes and Valence Isomers.
Bibliographische Angaben
- Autoren: A. -M. Caminade , M. Yoshifuji , S. Ito , M. Mikolajczyk , R. Streubel , J. -P. Majoral , J. G. Verkade , H. Heydt , T. P. Kee , T. D. Nixon , P. Balczewski
- 2002, 263 Seiten, Maße: 16 x 24,1 cm, Gebunden, Englisch
- Herausgegeben:Majoral, Jean-Pierre;Mitarbeit:Balczewski, P.; Caminade, A.-M.; Heydt, H.; Ito, S.; Kee, T.P.; Majoral, J.-P.; Mikolajczyk, M.; Nixon, T.D.; Streubel, R.; Verkade, J.G.; Yoshifuji, M.
- Herausgegeben: Jean-Pierre Majoral
- Verlag: Springer
- ISBN-10: 3540440860
- ISBN-13: 9783540440864
- Erscheinungsdatum: 27.11.2002
Sprache:
Englisch
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