Hammett studies of aryldichloromethide carbanion reactions

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1245-1247

  Moss, Robert A ^a   Tian, Jingzhi ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646460748     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060188c     Document Type: Article

References (13)

1. Moss, R. A.; Tian, J. J. Am. Chem. Soc. 2005, 127, 8960.
2. Lucius, R.; Mayr, H. Angew. Chem., Int. Ed. 2000, 39, 1995.
3. Review: Bernasconi, C. F. Tetrahedron 1989, 45, 4017.
4. Moss, R. A.; Terpinski, J.; Cox, D. P.; Denney, D. Z.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1985, 107, 2743.
5. Creary, X.; Sky, A. F.; Phillips, G. J. Org. Chem. 1990, 55, 2005 and references therein.
6. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
7. UV spectra of 3a-c at 77 K (3-methylpentane glass) and at ambient temperature (isooctane solution) are described in: Gould, I. R.; Turro, N. J.; Butcher, J., Jr.; Doubleday, C., Jr.; Hacker, N. P.; Lehr, G. F.; Moss, R. A.; Cox, D. P.; Guo, W.; Munjal, R. C.; Perez, L. A.; Fedorynski, M. Tetrahedron 1985, 41, 1587.
8. Celebi, S.; Tsao, M.-L.; Platz, M. S. J. Phys. Chem. A 2001, 105, 1158.
9. 4 and not readily visualized in this solvent.
10. Jones, M. B.; Maloney, V. M.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 2163. Electron-withdrawing substituents on ArCCl further slow Cl abstraction.
11. p-Methylphenylchlorocarbene did not appear to give the corresponding dichloromethide carbanion (LFP-UV)) with TBACl.
12. -.
13. - paired with a chiral cation. See for examples of asymmetric phase-transfer catalysis by chiral ammonium ions: Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.