-
1
-
-
0004200260
-
-
Brooks/Cole: Monterey, CA
-
See, e.g.: (a) McMurry, J. Organic Chemistry; Brooks/Cole: Monterey, CA, 1984; p 529 ff.
-
(1984)
Organic Chemistry
-
-
McMurry, J.1
-
3
-
-
0003922512
-
-
Prentice Hall: Upper Saddle River, NJ
-
(c) Wade, L. J., Jr. Organic Chemistry; Prentice Hall: Upper Saddle River, NJ, 1999; p 757 ff.
-
(1999)
Organic Chemistry
-
-
Wade Jr., L.J.1
-
9
-
-
0003672158
-
-
Wiley-Inter science: Hoboken, NJ
-
For the latest overview, see: Olah, G. A.; Molnar, A. Hydrocarbon Chemistry, 2nd ed.; Wiley-Interscience: Hoboken, NJ, 2003.
-
(2003)
Hydrocarbon Chemistry, 2nd Ed.
-
-
Olah, G.A.1
Molnar, A.2
-
10
-
-
18744409921
-
-
note
-
Insofar as X-ray structural parameters reflect molecular electron-density distributions.
-
-
-
-
12
-
-
18744408278
-
-
note
-
When a number of reactive intermediates are extant in solution, especially under equilibrium control, those which are isolated in crystal form generally depend on their solvation energy, crystal-lattice energy, molecular symmetry, etc., and not necessarily on their abundance (importance).
-
-
-
-
14
-
-
0000670569
-
-
For previous X-ray studies of analogous structures, mostly carried out at higher (room) temperature and lower precision, see: (a) Chevrier, B.; Le Carpentier, J.-H.; Weiss, R. Acta Crystallogr. 1972, B28, 2659, 2667.
-
(1972)
Acta Crystallogr.
, vol.B28
, pp. 2659
-
-
Chevrier, B.1
Le Carpentier, J.-H.2
Weiss, R.3
-
17
-
-
0040219854
-
-
(d) Chevrier, B.; Le Carpentier, J.-H.; Weiss, R. J. Am. Chem. Soc. 1972, 94, 5718.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 5718
-
-
Chevrier, B.1
Le Carpentier, J.-H.2
Weiss, R.3
-
18
-
-
0003748802
-
-
(e) Baroni, T. E.; Kolesnichenko, V.; Seib, L.; Heppert, J. A.; Liable-Sands, L. M.; Yap, G. P. A.; Rheingold, A. E. Polyhedron 1998, 17, 759.
-
(1998)
Polyhedron
, vol.17
, pp. 759
-
-
Baroni, T.E.1
Kolesnichenko, V.2
Seib, L.3
Heppert, J.A.4
Liable-Sands, L.M.5
Yap, G.P.A.6
Rheingold, A.E.7
-
19
-
-
11244258961
-
-
Davlieva, M. G.; Lindeman, S. V.; Neretin, I. S.; Kochi, J. K. New J. Chem. 2004, 28, 1568.
-
(2004)
New J. Chem.
, vol.28
, pp. 1568
-
-
Davlieva, M.G.1
Lindeman, S.V.2
Neretin, I.S.3
Kochi, J.K.4
-
20
-
-
33947330030
-
-
For X-ray diffraction studies at room temperature, see: (a) Boer, F. P. J. Am. Chem. Soc. 1988, 90, 6706.
-
(1988)
J. Am. Chem. Soc.
, vol.90
, pp. 6706
-
-
Boer, F.P.1
-
22
-
-
1642571938
-
-
(c) Chevrier, B.; Le Carpentier, J. M.; Weiss, R. Acta Crystallogr. 1972, B28, 2673.
-
(1972)
Acta Crystallogr.
, vol.B28
, pp. 2673
-
-
Chevrier, B.1
Le Carpentier, J.M.2
Weiss, R.3
-
23
-
-
0040219854
-
-
(d) Chevrier, B.; Le Carpentier, J. M.; Weiss, R. J. Am. Chem. Soc. 1972, 94, 5718.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 5718
-
-
Chevrier, B.1
Le Carpentier, J.M.2
Weiss, R.3
-
24
-
-
0042467244
-
-
Hurlburt, P. K.; Rack, J. J.; Luck, J. S.; Dec, S. F.; Webb, J. D.; Anderson, O. P.; Strauss, S. H. J. Am. Chem. Soc. 1994, 116, 10003.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 10003
-
-
Hurlburt, P.K.1
Rack, J.J.2
Luck, J.S.3
Dec, S.F.4
Webb, J.D.5
Anderson, O.P.6
Strauss, S.H.7
-
25
-
-
0000732489
-
-
(a) Olah, G. A.; Kuhn, S. J.; Tolgyesi, W. S.; Baker, E. B. J. Am. Chem. Soc. 1962, 84, 2733.
-
(1962)
J. Am. Chem. Soc.
, vol.84
, pp. 2733
-
-
Olah, G.A.1
Kuhn, S.J.2
Tolgyesi, W.S.3
Baker, E.B.4
-
26
-
-
0000889538
-
-
See also: Davlieva, M. G. et al. in ref 11
-
(b) Olah, G. A.; Tolgyesi, W. S.; Kuhn, S. J.; Moffat, M. E.; Bastien, I. J.; Baker, E. B. J. Am. Chem. Soc. 1963, 85, 1328. See also: Davlieva, M. G. et al. in ref 11.
-
(1963)
J. Am. Chem. Soc.
, vol.85
, pp. 1328
-
-
Olah, G.A.1
Tolgyesi, W.S.2
Kuhn, S.J.3
Moffat, M.E.4
Bastien, I.J.5
Baker, E.B.6
-
27
-
-
0001704282
-
-
For earlier conversions of acylium salts directly into Friedel-Crafts ketones, see: (a) Olah, G. A.; Kuhn, S. J.; Flood, S. H.; Hardie, B. A. J. Am. Chem. Soc. 1964, 86, 2203.
-
(1964)
J. Am. Chem. Soc.
, vol.86
, pp. 2203
-
-
Olah, G.A.1
Kuhn, S.J.2
Flood, S.H.3
Hardie, B.A.4
-
28
-
-
0003616463
-
-
(b) Olah, G. A.; Lukas, J.; Lukas, E. J. Am. Chem. Soc. 1969, 91, 5319.
-
(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 5319
-
-
Olah, G.A.1
Lukas, J.2
Lukas, E.3
-
29
-
-
84985602699
-
-
See also Olah et al. in ref 14
-
(c) Olah, G. A.; Lin, H. C.; Germain, A. Synthesis 1974, 12, 895. See also Olah et al. in ref 14.
-
(1974)
Synthesis
, vol.12
, pp. 895
-
-
Olah, G.A.1
Lin, H.C.2
Germain, A.3
-
30
-
-
18744414334
-
-
note
-
(a) We were limited in our mechanistic objectives (vide infra) to these difficult (low-temperature) experimental problems, so it is important to emphasize the caveat that the GC-MS analyses in Table S2 (and Table S3) were not required to be highly reproducible. The semiquantitative results are thus primarily intended to convey the relative trends in arene conversions to Friedel-Crafts ketones, as well as arene recovery and byproduct formation under low-temperature conditions.
-
-
-
-
31
-
-
18744392934
-
-
note
-
(b) For the synthetic utility of acylium salts, see the extensive studies of Olah et al. cited in ref 15.
-
-
-
-
34
-
-
0000038573
-
-
(c) Rathore, R.; Loyd, S. H.; Kochi, J. K. J. Am. Chem. Soc. 1994, 116, 8414.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 8414
-
-
Rathore, R.1
Loyd, S.H.2
Kochi, J.K.3
-
35
-
-
0032561771
-
-
(d) Rathore, R.; Hecht, J.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 13278.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 13278
-
-
Rathore, R.1
Hecht, J.2
Kochi, J.K.3
-
37
-
-
70349303334
-
-
(b) Schmidbaur, H.; Nowak, R.; Schier, A.; Wallis, J. M.; Huber, B.; Mueller, G. Chem. Ber. 1987, 120, 1829.
-
(1987)
Chem. Ber.
, vol.120
, pp. 1829
-
-
Schmidbaur, H.1
Nowak, R.2
Schier, A.3
Wallis, J.M.4
Huber, B.5
Mueller, G.6
-
38
-
-
0000214175
-
-
(a) Iverson, D. J.; Hunter, G.; Blount, J. F.; Damewood, J. R., Jr.; Mislow, K. J. Am. Chem. Soc. 1981, 103, 6073.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 6073
-
-
Iverson, D.J.1
Hunter, G.2
Blount, J.F.3
Damewood Jr., J.R.4
Mislow, K.5
-
39
-
-
0001052908
-
-
(b) Hunter, G.; Iverson, D. J.; Mislow, K.; Blount, J. F. J. Am. Chem. Soc. 1980, 102, 5942.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 5942
-
-
Hunter, G.1
Iverson, D.J.2
Mislow, K.3
Blount, J.F.4
-
40
-
-
37049066786
-
-
(c) Hunter, G.; Weakley, T. J. R.; Mislow, K.; Wong, M. G. J. Chem. Soc., Dalton Trans. 1986, 577.
-
(1986)
J. Chem. Soc., Dalton Trans.
, pp. 577
-
-
Hunter, G.1
Weakley, T.J.R.2
Mislow, K.3
Wong, M.G.4
-
41
-
-
0030831029
-
-
Rathore, R.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 9393.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 9393
-
-
Rathore, R.1
Lindeman, S.V.2
Kochi, J.K.3
-
42
-
-
18744374298
-
-
note
-
+ also have similar absorptions in this region but are generally blue-shifted by about 5-10 nm.
-
-
-
-
43
-
-
0007624883
-
-
(b) Mamatyuk, V. I.; Rezvukhin, A. I.; Detsina, A. V.; Buraev, V. I.; Isaev, I. S.; Koptyug, V. A. Zh. Org. Khim. 1973, 9, 2429.
-
(1973)
Zh. Org. Khim.
, vol.9
, pp. 2429
-
-
Mamatyuk, V.I.1
Rezvukhin, A.I.2
Detsina, A.V.3
Buraev, V.I.4
Isaev, I.S.5
Koptyug, V.A.6
-
46
-
-
18744391225
-
-
note
-
(a) The relative acceptor properties of the carbocations can be judged by differences in their reduction potentials.
-
-
-
-
47
-
-
33845278203
-
-
See: (b) Wayner, D. D. M.; McPhee, D. J.; Griller, D. J. Am. Chem. Soc. 1988, 110, 132.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 132
-
-
Wayner, D.D.M.1
McPhee, D.J.2
Griller, D.3
-
48
-
-
0035915374
-
-
and references therein
-
(c) Lund, T.; Wayner, D. D. M.; Jonsson, M.; Larsen, A. G.; Daasbjerg, K. J. Am. Chem. Soc. 2001, 123, 12590 and references therein.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 12590
-
-
Lund, T.1
Wayner, D.D.M.2
Jonsson, M.3
Larsen, A.G.4
Daasbjerg, K.5
-
50
-
-
18744403820
-
-
note
-
10,12 was limited to 1-1.5 pm (largely owing to thermal motion) in contrast to 0.3-0.5 pm from our low-temperature data.
-
-
-
-
51
-
-
3242850248
-
-
(b) The bond lengths for C=O and C-Cl of 1.181 and 1.804 Å that were determined in hydrocinnamoyl chloride at -150 °C generally fall in the range (1.16-1.21 and 1.75-1.83 Å) of those in other acid chlorides typically reported by: Leser, J.; Rabinovich, D. Acta Crystallogr. 1978, B34, 2253, 2257, 2260, 2264.
-
(1978)
Acta Crystallogr.
, vol.B34
, pp. 2253
-
-
Leser, J.1
Rabinovich, D.2
-
52
-
-
0006109808
-
-
Fukushima, S.; Ito, Y.; Hosomi, H.; Ohba, S. Acta Crystallogr. 1998, B54, 895.
-
(1998)
Acta Crystallogr.
, vol.B54
, pp. 895
-
-
Fukushima, S.1
Ito, Y.2
Hosomi, H.3
Ohba, S.4
-
54
-
-
0003438540
-
-
Cornell University Press: Ithaca, NY
-
(a) Pauling, L. Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960; p 239.
-
(1960)
Nature of the Chemical Bond
, pp. 239
-
-
Pauling, L.1
-
55
-
-
18744410230
-
-
note
-
1 = 1.48 Å and K = 0.50, which includes the correction for the change in covalent radius with hybridization.
-
-
-
-
56
-
-
18744389276
-
-
note
-
26b is possible, particularly with regard to solvation of the oxygen nonbonded electron pairs to induce acylium bending (vide infra). Unfortunately, the X-ray results do not address this possibility.
-
-
-
-
59
-
-
18744391790
-
-
note
-
Relative to the bond length of 1.07 Å estimated for a C=O triple bond as described by Davlieva et al. in ref 11 (footnote 18).
-
-
-
-
60
-
-
11344284526
-
-
3)-C(sp) bond length of 1.47 Å (Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1)
-
(1987)
J. Chem. Soc., Perkin Trans. 2
-
-
Allen, F.H.1
Kennard, O.2
Watson, D.G.3
Brammer, L.4
Orpen, A.G.5
Taylor, R.6
-
62
-
-
0003970635
-
-
Cambridge University Press: Cambridge, UK
-
(a) Schofield, K. Aromatic nitration; Cambridge University Press: Cambridge, UK, 1980.
-
(1980)
Aromatic Nitration
-
-
Schofield, K.1
-
64
-
-
0037454319
-
-
Gwaltney, S. R.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 3273.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 3273
-
-
Gwaltney, S.R.1
Rosokha, S.V.2
Head-Gordon, M.3
Kochi, J.K.4
-
65
-
-
0242600584
-
-
Esteves, P. M.; de Carneiro, J. W.; Cardoso, S. P.; Barbosa, A. G. H.; Laali, K. K.; Rasul, G.; Prakash, G. K. S.; Olah, G. A. J. Am. Chem. Soc. 2003, 125, 4836.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 4836
-
-
Esteves, P.M.1
De Carneiro, J.W.2
Cardoso, S.P.3
Barbosa, A.G.H.4
Laali, K.K.5
Rasul, G.6
Prakash, G.K.S.7
Olah, G.A.8
-
66
-
-
18744401194
-
-
Unpublished results
-
(a) Gwaltney, S. R. Unpublished results.
-
-
-
Gwaltney, S.R.1
-
67
-
-
18744371694
-
-
note
-
29 following Mulliken's theoretical classification of intermolecular interactions.
-
-
-
-
70
-
-
0001692003
-
-
Takahashi, Y.; Sankararaman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2954.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 2954
-
-
Takahashi, Y.1
Sankararaman, S.2
Kochi, J.K.3
-
71
-
-
0033802083
-
-
Hubig, S. M.; Lindeman, S. V.; Kochi, J. K. Coord. Chem. Rev. 2000, 200, 831.
-
(2000)
Coord. Chem. Rev.
, vol.200
, pp. 831
-
-
Hubig, S.M.1
Lindeman, S.V.2
Kochi, J.K.3
|