Reactivity and regiochemical behavior in the solvolysis reactions of (2,2-difluorocyclopropyl)methyl tosylates

Journal of Fluorine Chemistry

Volumn 119, Issue 1, 2003, Pages 39-51

  Battiste, Merle A ^a   Tian, Feng ^a   Baker, John M ^a   Bautista, Olivia ^a   Villalobos, Janette ^a   Dolbier, William R ^a  

^a University of Florida ^*  (United States)

Author keywords

(2,2 Difluorocyclopropyl)methyl radical and cation; DFT calculations; Kinetics; Solvolysis

Indexed keywords

FLUORINATED HYDROCARBON; METHYL GROUP; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DEGRADATION; MATHEMATICAL COMPUTING; RING OPENING;

EID: 0037207632     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(02)00248-8     Document Type: Article

References (14)

1. Tian F., Dolbier W.R. Jr. Org. Lett. 2:2000;835-837.
2. Tian F., Bartberger M.D., Dolbier W.R. J. Org. Chem. 64:1999;540-546.
3. Newcomb M., Chestney D.L. J. Am. Chem. Soc. 116:1994;9753-9754.
4. Koshy K.M., Tidwell T.T. J. Am. Chem. Soc. 102:1980;1216-1218.
5. Blint R.J., McMahon T.B., Beauchamp J.L. J. Am. Chem. Soc. 96:1974;1269-1278.
6. Tian F., Battiste M.A., Dolbier W.R. Jr. Org. Lett. 1:1999;193-196.
7. Bessard Y., Kuhlmann L., Schlosser M. Tetrahedron. 46:1990;5230-5236.
8. Boger D.L., Jenkins T.J. J. Am. Chem. Soc. 118:1996;8860-8870.
9. Wiberg K.B., Ashe A.J. Jr. J. Am. Chem. Soc. 90:1968;63-74.
10. Reich I.L., Diaz A., Winstein S. J. Am. Chem. Soc. 91:1969;5635-5637.
11. M.J.T. Frisch, G.W.H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J. Montgomery, J.A.R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.97, Gaussian Inc., Pittsburgh, PA, 1998.
12. Becke A.D. J. Chem. Phys. 98:1993;5648-5652.
13. Hariharan P.C., Pople J.A. Theor. Chem. Acta. 28:1973;213-222.
14. Raghavachari K., Trucks G.W. J. Chem. Phys. 91:1989;1062-1065.