First direct observation of the two distinct steps in an SN1 reaction

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4493-4495

  Mayr, Herbert ^a   Minegishi, Shinya ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Carbocations; Nucleophilic substitution; Reaction kinetics; Reactive intermediates; Solvent effects; Solvolysis

Indexed keywords

CARBON INORGANIC COMPOUNDS; IONIZATION OF LIQUIDS;

DISPLACEMENT REACTIONS;

SULFUR;

CARBENOID; TRIFLUOROETHANOL;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; REACTION TIME; SPECTROSCOPY;

EID: 0037011289     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4493::AID-ANIE4493>3.0.CO;2-U     Document Type: Article

References (22)

1. a) C. K. Ingold, E. Rothstein, J. Chem. Soc. 1928, 1217-1221;
2. C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd Ed., Cornell University, New York, 1969.
3. Carbonium Ions, Vol. 1-5 (Eds.: G. A. Olah, P. von R. Schleyer), Interscience, New York, 1968-1976.
4. P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985.
5. a) X. Creary, Advances in Carbocation Chemistry, Vol. 1, JAI, Greenwich, CT, 1989;
6. b) J. M. Coxon, Advances in Carbocation Chemistry, Vol. 2, JAI, Greenwich, CT, 1995.
7. a) "Carbocations": R. A. Cox in Organic Reaction Mechanisms (Eds.: A. C. Knipe, W. E. Watts), Wiley, Chichester, 1985-2001;
8. b) A. Streitwieser, Jr., Solvolytic Displacement Reactions, McGraw-Hill, New York, 1962.
9. G. A. Olah, W. S. Tolgyesi, S. J. Kuhn, M. E. Moffatt, I. J. Bastien, E. B. Baker, J. Am. Chem. Soc. 1963, 85, 1328-1334.
10. G. A. Olah, Angew. Chem. 1995, 107, 1519-1532; Angew. Chem. Int. Ed. Engl. 1995, 34, 1393-1405.
11. G. A. Olah, Angew. Chem. 1995, 107, 1519-1532; Angew. Chem. Int. Ed. Engl. 1995, 34, 1393-1405.
12. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957.
13. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957.
14. H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512.
15. R. A. McClelland, Tetrahedron 1996, 52, 6823-6858.
16. J. P. Richard, T. L. Amyes, M. M. Toteva, Acc. Chem. Res. 2001, 34, 981-988.
17. T. W. Bentley, G. Llewellyn, Prog. Phys. Org. Chem. 1990, 17, 121-158.
18. D. N. Kevill in Advances in Quantitative Structure-Property Relationships, Vol. 1 (Ed.: M. Charton), JAI, Greenwich, CT, 1996, pp. 81-115.
19. For salt effects in solvolysis reactions, see: D. J. Raber, J. M. Harris, P. von R. Schleyer in Ions and Ion Pairs in Organic Reactions, Vol. 2 (Ed.: M. Szwarc), Wiley, New York, 1974, pp. 247-374.
20. C. Schade, H. Mayr, Tetrahedron 1988, 44, 5761-5770.
21. C. A. Bunton, M. M. Mhala, J. R. Moffatt, J. Org. Chem. 1984, 49, 3639-3641.
22. J. Bartl, S. Steenken, H. Mayr, R. A. McClelland, J. Am. Chem. Soc. 1990, 112, 6918-6928.