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DOI: 10.1055/s-0033-1340059
Organic Superbases: The Concept at a Glance
Publication History
Received: 07 October 2013
Accepted: 08 October 2013
Publication Date:
20 November 2013 (online)
This Cluster is dedicated to the memory of Professor Manfred Schlosser
Abstract
The term ‘super base’ is generally applied to ionic metal-containing bases that undergo irreversible proton abstraction. However, non-ionic powerful amine derivatives of amidines, guanidines, phosphazenes, and Verkade’s bases with comparable or higher basicity to that of 1,8-bis(dimethylamino)naphthalene can all be arbitrarily classified as organic superbases. This Cluster contains manuscripts that present recent progress on organic superbases, including their applications in organic synthesis but, before proceeding, let us consider what class of molecule constitutes an organic superbase.
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References
- 1 Caubère P. Chem. Rev. 1993; 93: 2317
- 2 Schlosser M. Mod. Synth. Methods 1992; 6: 227
- 3 Haflinger G, Kuske FK. H In The Chemistry of Amidines and Imidates . Vol. 2; Patai S, Rapport Z. John Wiley & Sons; Chichester: 1991
- 4 Schwesinger R, Missfeldt M, Peters K, von Schnering HG. Angew. Chem., Int. Ed. Engl. 1987; 26: 1165
- 5 Kurzer F, Pitchfork ED. Fortschr. Chem. Forsch. 1968; 10: 375
- 6 Chamorro E, Escobar CA, Sienra R, Pérez P. J. Phys. Chem. A 2005; 109: 10068
- 7 Raczyńska ED, Cyrański MK, Gutowski M, Rak J, Gal J.-F, Maria P.-C, Darowska M, Duczmal K. J. Phys. Org. Chem. 2003; 16: 91
- 8 Raczyńska ED, Maria P.-C, Gal J.-F, Decouzon M. J. Phys. Org. Chem. 1994; 7: 725
- 9 Schwesinger R. Chimica 1985; 39: 269
- 10a Schwesinger R, Schlemper H. Angew. Chem., Int. Ed. Engl. 1987; 26: 1167
- 10b Schwesinger R, Hasenfratz C, Schlemper H, Walz L, Peters E.-M, von Schnering HG. Angew. Chem., Int. Ed. Engl. 1993; 32: 1361
- 11a Schwesinger R, Schlemper H, Hasenfratz C, Willaredt J, Dambacher T, Breuer T, Ottaway C, Fletschinger M, Boele J, Fritz H, Putzas D, Rotter HE, Bordwell FG, Satisch AV, Ji GZ, Peters E.-M, Peters K, von Schnering HG, Walz L. Liebig Ann. 1996; 1055
- 11b Koppel IA, Schwesinger R, Breuer T, Burk P, Herodes K, Koppel I, Leito I, Mishima M. J. Phys. Chem. A 2001; 105: 9575
- 12a Allen CW. Coord. Chem. Rev. 1994; 130: 137
- 12b Allen CW. Organophosphorus Chem. 1996; 27: 308
- 12c Kondo Y, Ueno M, Tanaka Y. J. Synth. Org. Chem. 2005; 63: 453
- 13a Kisanga PB, Verkade JG, Schwesinger R. J. Org. Chem. 2000; 65: 5431
- 13b Verkade JG, Kisanga PB. Tetrahedron 2003; 59: 7819
- 13c Verkade JG, Kisanga PB. Aldrichimica Acta 2004; 37: 3
- 14a Alder RW, Bowman PS, Steele WR. S, Winterman DR. Chem. Commun. 1968; 723
- 14b Alder RW, Bryce MR, Goode NC, Miller N, Owen J. J. Chem. Soc., Perkin Trans. 1 1981; 2840
- 15 Raab V, Kipke J, Gschwind RM, Sundermeyer J. Chem. Eur. J. 2002; 8: 1682
- 16 Kolomeitsev AA, Koppel IA, Rodima T, Barten J, Lork E, Röschenthaler G.-V, Kaljurand I, Kütt A, Koppel I, Mäemets V, Leito I. J. Am. Chem. Soc. 2005; 127: 17656
- 17 Kovacevic B, Maskic ZB. Chem. Eur. J. 2002; 8: 1694