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On the importance of leaving group ability in reactions of ammonium, oxonium, phosphonium, and sulfonium ylides

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Aggarwal, Varinder K. [University of Bristol] Harvey, Jeremy N. [University of Bristol] Robiette, Raphaël [UCL]
Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2005
Language Anglais
Journal information "Angewandte Chemie (International Edition)" - Vol. 44, no. 34, p. 5468-5471 (2005)
Peer reviewed yes
Publisher Wiley - V C H Verlag GmbH & Co. KGaA ((Germany) Weinheim)
issn 1433-7851
e-issn 1521-3773
Publication status Publié
Affiliations University of Bristol - School of Chemistry
UCL - SC/CHIM - Département de chimie
Links
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  2. Phosphorus Ylides, ISBN:9783527613908, 10.1002/9783527613908
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  38. It has been noted previously that thermodynamic property of basicity correlates with leaving group ability (kinetic property): species with low basicity have high leaving group ability (see , Organic Chemistry, W. H. Freeman, New York, 1998). However, this trend is not strictly followed by the present groups: phosphines and amines have similar basicity (pKa of Et3NH+ and Et3PH+ are respectively 9.0 and 9.1 in DMSO; see
  39. D. H. Ripin and D. A. Evans pKa's table at http://daecr1.harvard.edu/pdf/evans_pKa_table.pdf) yet phosphines are much poorer leaving groups.
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Bibliographic reference Aggarwal, Varinder K. ; Harvey, Jeremy N. ; Robiette, Raphaël. On the importance of leaving group ability in reactions of ammonium, oxonium, phosphonium, and sulfonium ylides. In: Angewandte Chemie (International Edition), Vol. 44, no. 34, p. 5468-5471 (2005)
Permanent URL http://hdl.handle.net/2078/76453