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Volumn 118, Issue 11, 1996, Pages 2556-2563

Novel keto-enol systems: Cyclobutane derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE;

EID: 0029917567     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952998h     Document Type: Article
Times cited : (30)

References (53)
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    • note
    • Hevafluorocyclobutanone is also highly hygroscopic, and it forms a very stable hydrate (see ref 14).
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    • Luttle would be gained from the allylic interaction, as judged from calculations which predict that the perfluoroallyl anion will be grossly nonplanar and that the classical planar structure will he far higher and not even be a potential energy minimum. Dixon, D. A., Fukunaga, T.; Smart, B. E. J. Phys Org Chem. 1988, 1, 153.
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    • the Spartan package of programs (Hehre, W.; Wavefunction, Inc.; 188401 Von Karman, Suite 370. Irvine, CA 92717) and
    • The calculations were carried out using (a) the Spartan package of programs (Hehre, W.; Wavefunction, Inc.; 188401 Von Karman, Suite 370. Irvine, CA 92717) and (b) Gaussian 92. Revision C.3 (Frisch. M J . Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wons, M. W.; Foresman, J B.; Johnson, B. G . Schelegel, H. B.; Robb, M. A.; Replogle, E S.; Gomperts, R.; Andres, J. L., Raghavachari, K., Binkley J. S.; Gonzalez, C . Martin, R. L.; Fox, D. J.; Defrees, D. J . Baker, J.; Stewart, J. J. P ; Pople, J. A . Gaussian, Inc . Pittsburgh, PA. 1992).
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    • At the HF/STO-3G//STO-3G level the energy gap for 1/2 is 13.0 kcal/mol.
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    • note
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    • At this level of theory, cyclobutanone itself is more stable than its enol by 196 kcal/mol. On the basis of thermochemical group equivalents. this energy difference was estimated to be 18.7 kcal/mol (Brickhouse. M. D.; Squires, R. R. J. Phys Org. Chem 1989, 2, 389).
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    • Apeloig, Y. In ref 2. Chapter 1. p 1
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