-
1
-
-
0000435481
-
-
and references therein
-
(a) Lautens, M.; Edwards, L. G.; Tam, W.; Lough, A. J. J. Am. Chem. Soc. 1995, 117, 10276 and references therein.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 10276
-
-
Lautens, M.1
Edwards, L.G.2
Tam, W.3
Lough, A.J.4
-
3
-
-
0000217950
-
-
(c) Paddon-Row, M. N.; Cotsaris, E.; Patney, H. K. Tetrahedron 1986, 42, 1779.
-
(1986)
Tetrahedron
, vol.42
, pp. 1779
-
-
Paddon-Row, M.N.1
Cotsaris, E.2
Patney, H.K.3
-
4
-
-
33845282528
-
-
(d) Oevering, H.; Paddon-Row, M. N.; Heppener, H.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. W.; Hush. N. S. J. Am. Chem. Soc. 1987, 109, 3258.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 3258
-
-
Oevering, H.1
Paddon-Row, M.N.2
Heppener, H.3
Oliver, A.M.4
Cotsaris, E.5
Verhoeven, J.W.6
Hush, N.S.7
-
7
-
-
33947088328
-
-
Tabushi, I.; Yamamura, K.; Yoshida, Z. J. Am. Chem. Soc. 1972, 94, 787.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 787
-
-
Tabushi, I.1
Yamamura, K.2
Yoshida, Z.3
-
8
-
-
33845280964
-
-
Paquette, L. A.; Kesselmayer, M. A.; Künzer, H. J. Org. Chem. 1988, 55, 5183.
-
(1988)
J. Org. Chem.
, vol.55
, pp. 5183
-
-
Paquette, L.A.1
Kesselmayer, M.A.2
Künzer, H.3
-
10
-
-
0345491105
-
-
(b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
11
-
-
0344791553
-
-
For reviews of density-functional methods, see: (c) Ziegler, T. Chem. Rev. 1991, 91, 651. (d) Density Functional Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer: Berlin, 1991. (e) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
-
(1991)
Chem. Rev.
, vol.91
, pp. 651
-
-
Ziegler, T.1
-
12
-
-
0003442182
-
-
Springer: Berlin
-
For reviews of density-functional methods, see: (c) Ziegler, T. Chem. Rev. 1991, 91, 651. (d) Density Functional Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer: Berlin, 1991. (e) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
-
(1991)
Density Functional Methods in Chemistry
-
-
Labanowski, J.1
Andzelm, J.2
-
13
-
-
0003569570
-
-
Oxford University Press: New York
-
For reviews of density-functional methods, see: (c) Ziegler, T. Chem. Rev. 1991, 91, 651. (d) Density Functional Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer: Berlin, 1991. (e) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
-
(1989)
Density-Functional Theory of Atoms and Molecules
-
-
Parr, R.G.1
Yang, W.2
-
14
-
-
0004133516
-
-
Gaussian Inc.: Pittsburgh, PA
-
All calculations were performed with Gaussian 94: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Latham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 (Revision B); Gaussian Inc.: Pittsburgh, PA, 1994.
-
(1994)
Gaussian 94 (Revision B)
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Gill, P.M.W.4
Johnson, B.G.5
Robb, M.A.6
Cheeseman, J.R.7
Keith, T.8
Petersson, G.A.9
Montgomery, J.A.10
Raghavachari, K.11
Al-Latham, M.A.12
Zakrzewski, V.G.13
Ortiz, J.V.14
Foresman, J.B.15
Cioslowski, J.16
Stefanov, B.B.17
Nanayakkara, A.18
Challacombe, M.19
Peng, C.Y.20
Ayala, P.Y.21
Chen, W.22
Wong, M.W.23
Andres, J.L.24
Replogle, E.S.25
Gomperts, R.26
Martin, R.L.27
Fox, D.J.28
Binkley, J.S.29
Defrees, D.J.30
Baker, J.31
Stewart, J.P.32
Head-Gordon, M.33
Gonzalez, C.34
Pople, J.A.35
more..
-
15
-
-
33748960439
-
-
and references therein
-
Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1, 682 and references therein.
-
(1992)
Angew. Chem., Int. Ed. Engl.
, vol.31
, Issue.1
, pp. 682
-
-
Houk, K.N.1
Li, Y.2
Evanseck, J.D.3
-
16
-
-
0030018945
-
-
B3LYP/6-31G(d) DFT has proved to give excellent results in comparisons of biradical and concerted mechanisms for pericyclic reactions. See, for example: (a) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036. (b) Houk, K. N.; Beno, B. R.; Nendel, M.; Black, K.; Yoo, H. Y.; Wilsey, S.; Lee, J. K. J. Mol. Struct. (Theochem) 1997, 398-399, 169.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 6036
-
-
Goldstein, E.1
Beno, B.2
Houk, K.N.3
-
17
-
-
30244518651
-
-
B3LYP/6-31G(d) DFT has proved to give excellent results in comparisons of biradical and concerted mechanisms for pericyclic reactions. See, for example: (a) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036. (b) Houk, K. N.; Beno, B. R.; Nendel, M.; Black, K.; Yoo, H. Y.; Wilsey, S.; Lee, J. K. J. Mol. Struct. (Theochem) 1997, 398-399, 169.
-
(1997)
J. Mol. Struct. (Theochem)
, vol.398-399
, pp. 169
-
-
Houk, K.N.1
Beno, B.R.2
Nendel, M.3
Black, K.4
Yoo, H.Y.5
Wilsey, S.6
Lee, J.K.7
-
18
-
-
0344550040
-
-
note
-
(a) Conformations a, b, and c for the acetylene-quadricyclane system are characterized by the value of the dihedral angle C9-C8-C1-C5: a, ∼0°; b, ∼130°; c, ∼230°. Conformation 4b has a dihedral angle of 159°. Conformation 4c does not exist. (b) Conformations for the ethylene-quadricyclane system are characterized by the dihedral angle C9-C8-C1-C5: a, ∼65°; b, ∼180°; c, ∼315°.
-
-
-
-
19
-
-
0001122813
-
-
and references therein
-
Strozier, R. W.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 1340 and references therein.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 1340
-
-
Strozier, R.W.1
Caramella, P.2
Houk, K.N.3
-
20
-
-
0344980987
-
-
note
-
There are two other conformations of 7, namely 7b and 7c, which are able to take the indirect route depicted in Scheme 2. However, the transition structure, 8a, for the direct conversion of 7a into 2 lies, respectively, 3.0 and 4.2 kcal/mol lower in energy than the transition structures for the conversion of 7b and 7c into the respective norbornenyl biradicals 9b and 9c. The direct pathway, proceeding from 7a, is therefore favored. The dihedral angle C9-C8-C1-C5 is 5.8° for 7a, 130° for 7b, and 236° for 7c. See Supporting Information for further details.
-
-
-
-
21
-
-
0345412259
-
-
note
-
2〉 of the UB3LYP/6-31G(d) wave function for biradical transition structure 4a is 0.1.
-
-
-
-
22
-
-
0344118394
-
-
note
-
Details can be found in the Supporting Information.
-
-
-
-
24
-
-
0030668117
-
-
See, for example: Houk, K. N.; Nendel, M.; Wiest, O.; Storer, J. W. J. Am. Chem. Soc. 1997, 119, 10545.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10545
-
-
Houk, K.N.1
Nendel, M.2
Wiest, O.3
Storer, J.W.4
-
25
-
-
0344550039
-
-
note
-
D1 is defined (ref 4) as the ratio of product arising from attack of the reagent at C6 and C7 of 18 to that formed from attack at C1 and C5.
-
-
-
-
26
-
-
9344269016
-
-
6 or the program QUIVER (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989.)
-
(1995)
J. Phys. Chem.
, vol.99
, pp. 3093
-
-
Rauhut, G.1
Pulay, P.2
-
27
-
-
0024841752
-
-
6 or the program QUIVER (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989.)
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 8989
-
-
Saunders, M.1
Laidig, K.E.2
Wolfsberg, M.3
-
28
-
-
0345412258
-
-
note
-
Labeled quadricyclanes were synthesized by photochemical closure of the corresponding labeled norbornadienes, which were in turn prepared by H/D exchange and Shapiro reaction on the corresponding ketones. Details are given in the Supporting Information.
-
-
-
-
29
-
-
0344550037
-
-
note
-
See Table 1 for an explanation of SKIE nomenclature.
-
-
-
-
35
-
-
0003133511
-
-
For EA of the diethyl ester, see: Marken, F.; Compton, R. G.; Bull, S. D.; Davies, S. G. J. Chem. Soc. Chem. Commun. 1997, 995.
-
(1997)
J. Chem. Soc. Chem. Commun.
, pp. 995
-
-
Marken, F.1
Compton, R.G.2
Bull, S.D.3
Davies, S.G.4
-
36
-
-
84984303074
-
-
and references therein
-
See, for example: Kim, E.; Christi, M.; Kochi, J. K. Chem. Ber. 1990, 123, 1209 and references therein.
-
(1990)
Chem. Ber.
, vol.123
, pp. 1209
-
-
Kim, E.1
Christi, M.2
Kochi, J.K.3
-
37
-
-
37049084636
-
-
Kim, T.; Sarker, H.; Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 1995, 577.
-
(1995)
J. Chem. Soc., Perkin Trans. 2
, pp. 577
-
-
Kim, T.1
Sarker, H.2
Bauld, N.L.3
-
38
-
-
0023542006
-
-
(a) Gebicki, J. L.; Gebicki, J.; Mayer, J. Radiat. Phys. Chem. 1987, 30, 165.
-
(1987)
Radiat. Phys. Chem.
, vol.30
, pp. 165
-
-
Gebicki, J.L.1
Gebicki, J.2
Mayer, J.3
-
39
-
-
0000984475
-
-
(b) Bach, R. D.; Schilke, I. L.; Schlegel, H. B. J. Org. Chem. 1996, 61, 4845.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4845
-
-
Bach, R.D.1
Schilke, I.L.2
Schlegel, H.B.3
-
40
-
-
3242849579
-
-
(c) Ishiguro, K.; Khudyakov, I. V.; McGarry, P. F.; Turro, N. J.; Roth, H. D. J. Am. Chem. Soc. 1994, 116, 6933.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 6933
-
-
Ishiguro, K.1
Khudyakov, I.V.2
McGarry, P.F.3
Turro, N.J.4
Roth, H.D.5
-
41
-
-
0011779394
-
-
Barwise, A. J. G.; Gorman, A. A.; Leyland, R. L.; Parekh, C. T.; Smith, P. G. Tetrahedron 1980, 36, 397.
-
(1980)
Tetrahedron
, vol.36
, pp. 397
-
-
Barwise, A.J.G.1
Gorman, A.A.2
Leyland, R.L.3
Parekh, C.T.4
Smith, P.G.5
|