Synthesis and reactivity of the methylene arenium form of a benzyl cation, stabilized by complexation

Journal of the American Chemical Society

Volumn 128, Issue 51, 2006, Pages 16450-16451

  Poverenov, Elena ^a   Leitus, Gregory ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; CARBENE; CATION; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

BENZENE DERIVATIVES; CATIONS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 33845934221     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067298z     Document Type: Article

References (20)

1. Olah, G. A.; Prakash, G. K. S. Carbocation Chemistry; Wiley & Sons: New York, 2004.
2. (a) Olah, G. A. J. Am. Chem. Soc. 1964, 86, 932.
3. (b) Bollinger, J. M.; Comisarow, M. B.; Cupas, C. A.; Olah, G. A. J. Am. Chem. Soc. 1967, 89, 5687.
4. (c) Olah, G. A.; Porter, R. D.; Jeuell, C. L.; White, A. M. J. Am. Chem. Soc. 1972, 94, 2044.
5. (d) Heagy, M. D.; Wang, Q.; Olah, G. A.; Prakash, G. K. S. J. Org. Chem. 1995, 60, 7355.
6. Van Pelt, P.; Buck, H. M. Recl. Trav. Chim. Pays-Bas 1973, 92, 1057.
7. Reindl, B.; Clark, T.; Scheleyer, P.v. R. J. Phys. Chem. A 1998, 102, 8953.
8. Vigalok, A.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 477.
9. Transition metal stabilized arenium cations (not methylene arenium): (a) Albrecht, M.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 2001, 123, 7233.
10. (b) Keane, J. M.; Chordia, M. D.; Mocella, C. J.; Sabat, M.; Trindle, C. D.; Harman, W. D. J. Am. Chem. Soc. 2004, 126, 6806.
11. Rabin, O.; Vigalok, A.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 7119.
12. See Supporting Information.
13. Laube, T.; Olah, G. A.; Bau, R. J. Am. Chem. Soc. 1997, 119, 3087.
14. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H. J.; Krueger, C. Organometallics 1983, 2, 1369.
15. Burrows, A. D.; Choi, N.; McPartlin, M.; Mingos, D. M. P.; Tarlton, S. V.; Vilar, R. Organomet. Chem. 1999, 573, 313.
16. Vigalok, A. Milstein, D. Acc. Chem. Res. 2001, 34, 798.
17. Seip, H. M.; Seip, R. Acta Chem. Scand. 1973, 27, 4024.
18. Sneen, R. A.; Felt, G. R.; Dickason, W. C. J. Am. Chem. Soc. 1973, 95, 638.
19. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley & Sons: New York, 1981; p 88.
20. Vigalok, A.; Rybtchinski, B.; Gozin, Y.; Koblenz, T. S.; Ben-David, Y.; Rozenberg, H.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 15692.