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15844390115
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For a concise summary of this work, see: Hart, H., Rappoport, Z.; Biali, S. E In ref 1. pp 502-14.
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6
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15844423338
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(a) Bekker, R. A : Popkova, V. Ya., Knunyants, I. L. Dokl. Akad Nauk SSSK 1976, 229, 870: Dokl. Akad. Nauk SSSR, Engl. Transl. 1976. 229, 514.
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15844381785
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(a) Bekker, R. A : Popkova, V. Ya., Knunyants, I. L. Dokl. Akad Nauk SSSK 1976, 229, 870: Dokl. Akad. Nauk SSSR, Engl. Transl. 1976. 229, 514.
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Dokl. Akad. Nauk SSSR, Engl. Transl.
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8
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15844422516
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(b) Bekker, R. A.; Popkova, V. Ya.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1976, 231, 864; Dokl. Akad. Nauk SSSR, Engl. Transl. 1976. 231, 700. Bekker, R. A.; Popkova, V. Ya.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1977, 235, 103, Dokl. Akad. Nauk SSSR, Engl. Transl. 1977, 235, 370
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(b) Bekker, R. A.; Popkova, V. Ya.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1976, 231, 864; Dokl. Akad. Nauk SSSR, Engl. Transl. 1976. 231, 700. Bekker, R. A.; Popkova, V. Ya.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1977, 235, 103, Dokl. Akad. Nauk SSSR, Engl. Transl. 1977, 235, 370
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15844374344
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15844376536
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24
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15844417092
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note
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Hevafluorocyclobutanone is also highly hygroscopic, and it forms a very stable hydrate (see ref 14).
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25
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1542580750
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Remarkable enols stabilized by oxygen and chlorine substituents have recently been described. they approach 3 in stability. Ettlinger. M G.; Watson, K. J.; Jaroszewski, J. W. J. Am Chem Soc. 1994, 116, 1557 See also Nadler, B ; Rappoport, Z., Arad, Y.; Apeloig, Y J. Am Chem. Soc 1987, 109, 7873.
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26
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0010780457
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Remarkable enols stabilized by oxygen and chlorine substituents have recently been described. they approach 3 in stability. Ettlinger. M G.; Watson, K. J.; Jaroszewski, J. W. J. Am Chem Soc. 1994, 116, 1557 See also Nadler, B ; Rappoport, Z., Arad, Y.; Apeloig, Y J. Am Chem. Soc 1987, 109, 7873.
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Nadler, B.1
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Apeloig, Y.4
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27
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15844429212
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note
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In contrast, there was no evidence of a bimolecular reaction between enol 4 and ketone 3 at a concentration of 0.03 M.
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28
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15844391508
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh, Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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Bekker, R.A.1
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Dyatkin, B.L.4
Knunyants, I.L.5
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15844408902
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh. Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh. Org. Khim., Engl. Transl. 1977, 13, 1461
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh. Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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Bekker, R.A.1
Melikyan, G.G.2
Dyatkin, B.L.3
Knunyants, I.L.4
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh, Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh. Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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Dyatkin, B.L.3
Knunyants, I.L.4
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh. Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh, Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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Bekker, R.A.1
Badanyan, Sh.O.2
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Knunyants, I.L.4
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15844378649
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Bekker, R. A.; Melikyan., G. G.; Lur'e. É. P.; Dyatkin, B. L.; Knunyants, I. L. Dokl. Akad. Nauk SSSR 1974, 217, 1320: Dokl. Akad. Nauk SSSR. Engl. Transl. 1974, 217, 572. Bekker, R. A., Melikyan, G. G : Dyatkin, B. L.; Knunyants, I. L. Zh, Org. Khim. 1975, 11, 1370. Zh. Org. Khim., Engl. Transl. 1975, 11, 1356. Bekker, R. A., Melikyan, G. G.; Dyatkin, B. L.; Knunyants, I L. Zh. Org. Khim. 1975, 11, 2370: Zh. Org. Khim., Engl. Transl. 1975, 11. 2415. Bekker, R. A., Badanyan, Sh O.; Melikyan, G. G ; Knunyants, I. L. Zh. Org Khim. 1977. 13. 1582; Zh Org. Khim., Engl. Transl. 1977, 13, 1461
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0005397358
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Kresge, A. J.; Chen, H J. J. Am. Chem. Soc 1972, 94, 2818. Kresge, A. J.; Sagatys, D. S., Chen, H. C. J. Am. Chem. Soc. 1977, 99 7228.
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0000755059
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Kresge, A. J.; Chen, H J. J. Am. Chem. Soc 1972, 94, 2818. Kresge, A. J.; Sagatys, D. S., Chen, H. C. J. Am. Chem. Soc. 1977, 99 7228.
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38
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15844392598
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note
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The reaction mixture was heterogeneous, with the acid layer settling to the bottom of the tube. For efficient reaction the tube had to be shaken vigorously
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-
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39
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15844425301
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2 carbons substantially decrease the reactivity of the double bond toward electrophilic reagents See. for example. Pohshchuk, V. R., Mysov, E I., Stankevitch, I. V . Chistyakov, A. L ; Potechin, K. A., Struchkov, Yu.T J. Fluorine Chem. 1993, 65, 233.
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Pohshchuk, V.R.1
Mysov, E.I.2
Stankevitch, I.V.3
Chistyakov, A.L.4
Potechin, K.A.5
Struchkov, Yu.T.6
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40
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15844423337
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John Wiley & Sons. New York
-
For the reaction of benzene with tert-butyl cation. see. March, J. Adtanced Organic Chemistry, 4th ed.; John Wiley & Sons. New York, 1992, p 535.
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Adtanced Organic Chemistry, 4th Ed.
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March, J.1
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41
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84986992497
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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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Dixon, D.A.1
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Smart, B.E.3
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42
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15844377912
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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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43
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0004133516
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Gaussian, Inc . Pittsburgh, PA.
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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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(1992)
Gaussian 92. Revision C.3
-
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Frisch, M.J.1
Trucks, G.W.2
Head-Gordon, M.3
Gill, P.M.W.4
Wons, M.W.5
Foresman, J.B.6
Johnson, B.G.7
Schelegel, H.B.8
Robb, M.A.9
Replogle, E.S.10
Gomperts, R.11
Andres, J.L.12
Raghavachari, K.13
Binkley, J.S.14
Gonzalez, C.15
Martin, R.L.16
Fox, D.J.17
Defrees, D.J.18
Baker, J.19
Stewart, J.J.P.20
Pople, J.A.21
more..
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44
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0000039989
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Liebman, J F., Greenberg, A., Eds.; VCH Publishers Deerfield Beach, FL
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See, for example: Smart, B. E. In Molecular Structure and Energetics; Liebman, J F., Greenberg, A., Eds.; VCH Publishers Deerfield Beach, FL. 1986; Vol. 3. p 141.
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(1986)
Molecular Structure and Energetics
, vol.3
, pp. 141
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Smart, B.E.1
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45
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15844404411
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note
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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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46
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15844363691
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note
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The change in size of the energy gap in progressing from the 6-31G* to the 6-3IG** level seems surprising, as the only change in basis set is the addition of polarization functions on the lone hydrogen.
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47
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84986946019
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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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(1989)
J. Phys Org. Chem
, vol.2
, pp. 389
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Brickhouse, M.D.1
Squires, R.R.2
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48
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15844406051
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Apeloig, Y. In ref 2. Chapter 1. p 1
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(a) Apeloig, Y. In ref 2. Chapter 1. p 1
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52
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15844407724
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Buxton, M. W.; Ingram, D. W ; Smith, F.; Stacey, M.; Tatlov, J. C J. Chem. Soc. 1952, 3830.
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(1952)
J. Chem. Soc.
, vol.3830
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Buxton, M.W.1
Ingram, D.W.2
Smith, F.3
Stacey, M.4
Tatlov, J.C.5
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53
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15844366799
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Hurd, C. D . Audneth, L. F.; Nalefshi, L. A. Inorg. Synth. 1937, 1, 87.
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(1937)
Inorg. Synth.
, vol.1
, pp. 87
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Hurd, C.D.1
Audneth, L.F.2
Nalefshi, L.A.3
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