-
1
-
-
1842448719
-
Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles
-
New Orleans, LA, March 2003; American Chemical Society: Washington, DC; Abstract ORGN 503
-
Presented in part at the National Meeting of the American Chemical Society: Rendy, R.; Zhang, Y.; McElrea, A.; Gomez, A.; Dang, H.; Klumpp, D. A. Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles. In Abstracts of Papers, 225th National Meeting of the American Chemical Society, New Orleans, LA, March 2003; American Chemical Society: Washington, DC, 2003; Abstract ORGN 503.
-
(2003)
Abstracts of Papers, 225th National Meeting of the American Chemical Society
-
-
Rendy, R.1
Zhang, Y.2
McElrea, A.3
Gomez, A.4
Dang, H.5
Klumpp, D.A.6
-
2
-
-
33847801637
-
-
Olah, G. A.; Germain, A.; Lin, H. C.; Forsyth, D. J. Am. Chem. Soc. 1975, 97, 2928.
-
(1975)
J. Am. Chem. Soc.
, vol.97
, pp. 2928
-
-
Olah, G.A.1
Germain, A.2
Lin, H.C.3
Forsyth, D.4
-
3
-
-
33748224730
-
-
(a) Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 2, 767.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, Issue.2
, pp. 767
-
-
Olah, G.A.1
-
5
-
-
0001472217
-
-
Ohwada, T.; Okabe, K.; Ohta, T.; Shudo, K. Tetrahedron 1990, 46, 7539.
-
(1990)
Tetrahedron
, vol.46
, pp. 7539
-
-
Ohwada, T.1
Okabe, K.2
Ohta, T.3
Shudo, K.4
-
6
-
-
85021466962
-
-
Wiley: New York, Collect
-
(b) See also, Shildneck, P. R. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p 236.
-
(1943)
Organic Syntheses
, vol.2
, pp. 236
-
-
Shildneck, P.R.1
-
7
-
-
0000306182
-
-
Ohwada, T.; Ohta, T.; Shudo, K. J. Am. Chem. Soc. 1986, 108, 3092.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 3092
-
-
Ohwada, T.1
Ohta, T.2
Shudo, K.3
-
8
-
-
0033215075
-
-
Klumpp, D. A.; Garza, M.; Lau, S.; Shick, B.; Kantardjieff, K. J. Org. Chem. 1999, 64, 7635.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 7635
-
-
Klumpp, D.A.1
Garza, M.2
Lau, S.3
Shick, B.4
Kantardjieff, K.5
-
9
-
-
77951988451
-
-
Olah, G. A., Ed.; Wiley: New York, and references cited therewithin
-
(a) Koncos, R.; Friedman, B. S. In Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Wiley: New York, 1964; Vol 2, pp 318-320 and references cited therewithin
-
(1964)
Friedel-Crafts and Related Reactions
, vol.2
, pp. 318-320
-
-
Koncos, R.1
Friedman, B.S.2
-
13
-
-
0141883006
-
-
(e) Prakash, G. K. S.; Yan, P.; Torok, B.; Olah, G. A. Catal. Lett. 2003, 87(3-4), 109.
-
(2003)
Catal. Lett.
, vol.87
, Issue.3-4
, pp. 109
-
-
Prakash, G.K.S.1
Yan, P.2
Torok, B.3
Olah, G.A.4
-
14
-
-
1842448705
-
-
International Patent No. PCT/US99/00225, 1999, International Publ No WO 99/35119
-
(f) Moussa, A. M.; Haider, R.; Taft, H.; Jurayj, J.; Wang, W.; Suh, H. International Patent No. PCT/US99/00225, 1999, International Publ. No. WO 99/35119.
-
-
-
Moussa, A.M.1
Haider, R.2
Taft, H.3
Jurayj, J.4
Wang, W.5
Suh, H.6
-
15
-
-
1842500994
-
-
(g) Koelsch, C. F.; Hochmann, H.; Le Claire, C. D. J. Am. Chem. Soc. 1943, 65, 1521.
-
(1943)
J. Am. Chem. Soc.
, vol.65
, pp. 1521
-
-
Koelsch, C.F.1
Hochmann, H.2
Le Claire, C.D.3
-
17
-
-
1842448704
-
-
note
-
Trace quantities of the propanone products (6j-l) could also be detected by GCMS, however these minor products could not be isolated.
-
-
-
-
18
-
-
0000352409
-
-
(a) Okamato, Y.; Inukai, T.; Brown, H. C. J. Am. Chem. Soc. 1958, 80, 4969.
-
(1958)
J. Am. Chem. Soc.
, vol.80
, pp. 4969
-
-
Okamato, Y.1
Inukai, T.2
Brown, H.C.3
-
20
-
-
0026010517
-
-
Saito, S.; Saito, S.-i.; Ohwada, T.; Shudo, K. Chem. Pharm. Bull. 1991, 39, 2718.
-
(1991)
Chem. Pharm. Bull.
, vol.39
, pp. 2718
-
-
Saito, S.1
Saito, S.-I.2
Ohwada, T.3
Shudo, K.4
-
21
-
-
0001417043
-
-
Prakash, G. K. S.; Rasul, G.; Liang, G.; Olah, G. A. J. Phys. Chem. 1996, 100, 15805.
-
(1996)
J. Phys. Chem.
, vol.100
, pp. 15805
-
-
Prakash, G.K.S.1
Rasul, G.2
Liang, G.3
Olah, G.A.4
-
22
-
-
0141891692
-
-
Allen, J. M.; Johnson, K. M.; Jones, J. F.; Shotter, R. G. Tetrahedron 1977, 33, 2083.
-
(1977)
Tetrahedron
, vol.33
, pp. 2083
-
-
Allen, J.M.1
Johnson, K.M.2
Jones, J.F.3
Shotter, R.G.4
-
23
-
-
0030816069
-
-
Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 6774
-
-
Suzuki, T.1
Ohwada, T.2
Shudo, K.3
-
25
-
-
0004133516
-
-
Gaussian, Inc.: Pittsburgh, PA
-
(a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, R. E.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; M. Head-Gordon, M.; Pople, J. A. Gaussian 98, revision A.5; Gaussian, Inc.: Pittsburgh, PA, 1998.
-
(1998)
Gaussian 98, Revision A.5
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery, J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, R.E.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, G.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperts, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
Al-Laham, M.A.45
Peng, C.Y.46
Nanayakkara, A.47
Gonzalez, C.48
Challacombe, M.49
Gill, P.M.W.50
Johnson, B.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Gonzalez, C.55
Head-Gordon, M.56
Pople, J.A.57
more..
-
26
-
-
1842448710
-
-
note
-
(b) For details of the computational studies, see the Supporting Information.
-
-
-
-
28
-
-
0000755615
-
-
(b) Other peak assignments: 40.4 ppm, methylene carbon; 132.0 ppm, meta-position; 139.9 ppm, ortho-position; 143.4 ppm, ipso-position; 150.1 ppm, para-position. These assignments are made by comparison to other related diphenylmethyl cations, see: Olah, G. A.; Prakash, G. K. S.; Liang, G.; Westerman, P. W.; Kunde, K.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1980, 102, 4485.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 4485
-
-
Olah, G.A.1
Prakash, G.K.S.2
Liang, G.3
Westerman, P.W.4
Kunde, K.5
Chandrasekhar, J.6
Schleyer, P.V.R.7
-
29
-
-
0003471628
-
-
Patai, S., Rappoport, Z., Eds.; Wiley: New York
-
Boche, G., Walborsky, H. M. In Cyclopropane Derived Reactive Intermediates; Patai, S., Rappoport, Z., Eds.; Wiley: New York: 1990.
-
(1990)
Cyclopropane Derived Reactive Intermediates
-
-
Boche, G.1
Walborsky, H.M.2
-
30
-
-
33947086041
-
-
Elling, G. R.; Hahn, R. C.; Schwab, G. J. Am. Chem. Soc. 1973, 95, 5659.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 5659
-
-
Elling, G.R.1
Hahn, R.C.2
Schwab, G.3
-
31
-
-
0035936739
-
-
A similar monocationic ring opening has been proposed recently, see: Mohanta, P. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2001, 66, 1503.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 1503
-
-
Mohanta, P.K.1
Peruncheralathan, S.2
Ila, H.3
Junjappa, H.4
-
33
-
-
0035940126
-
-
Klumpp, D. A.; Aguirre, S. L.; Sanchez, G. V., Jr.; de Leon, S. J. Org. Lett., 2001, 3, 2781.
-
(2001)
Org. Lett.
, vol.3
, pp. 2781
-
-
Klumpp, D.A.1
Aguirre, S.L.2
Sanchez Jr., G.V.3
De Leon, S.J.4
-
34
-
-
0037872105
-
-
(a) Zhang, Y.; McElrea, A.; Sanchez, G. V., Jr.; Do, D.; Gomez, A.; Aguirre, S. L.; Rendy, R.; Klumpp, D. A. J. Org. Chem. 2003, 68, 5119.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 5119
-
-
Zhang, Y.1
McElrea, A.2
Sanchez Jr., G.V.3
Do, D.4
Gomez, A.5
Aguirre, S.L.6
Rendy, R.7
Klumpp, D.A.8
-
35
-
-
0035920621
-
-
(b) Klumpp, D. A.; Beauchamp, P. S.; Sanchez, G. S., Jr.; Aguirre, S.; de Leon, S. Tetrahedron Lett. 2001, 42 (34), 5821.
-
(2001)
Tetrahedron Lett.
, vol.42
, Issue.34
, pp. 5821
-
-
Klumpp, D.A.1
Beauchamp, P.S.2
Sanchez Jr., G.S.3
Aguirre, S.4
De Leon, S.5
-
36
-
-
0032886807
-
-
(c) Klumpp, D. A.; Garza, M.; Jones, A.; Mendoza, S. J. Org. Chem. 1999, 64, 6702
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6702
-
-
Klumpp, D.A.1
Garza, M.2
Jones, A.3
Mendoza, S.4
-
38
-
-
0033910329
-
-
(b) Klumpp, D. A.; Jones, A.; Lau, S.; DeLeon, S.; Garza, M. Synthesis 2000, 1117.
-
(2000)
Synthesis
, pp. 1117
-
-
Klumpp, D.A.1
Jones, A.2
Lau, S.3
DeLeon, S.4
Garza, M.5
-
39
-
-
0037073928
-
-
(c) Koltunov, K. Y.; Prakash, G. K. S.; Rasul, G.; Olah, G. A. J. Org. Chem. 2002, 67, 8943.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 8943
-
-
Koltunov, K.Y.1
Prakash, G.K.S.2
Rasul, G.3
Olah, G.A.4
-
40
-
-
0037119666
-
-
Zhang, Y.; Aguirre, S. A.; Klumpp, D. A. Tetrahedron Lett. 2002, 43, 6837.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 6837
-
-
Zhang, Y.1
Aguirre, S.A.2
Klumpp, D.A.3
-
41
-
-
0034731528
-
-
(a) Klumpp, D. A.; Garza, G.; Sanchez, G. V.; Lau, S.; DeLeon, S. J. Org. Chem. 2000, 65, 8997.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 8997
-
-
Klumpp, D.A.1
Garza, G.2
Sanchez, G.V.3
Lau, S.4
DeLeon, S.5
-
42
-
-
84985527621
-
-
(b) Prakash, G. K. S.; Rawdah, T. N.; Olah, G. A. Angew. Chem., Int. Ed. 1983, 22, 390.
-
(1983)
Angew. Chem., Int. Ed.
, vol.22
, pp. 390
-
-
Prakash, G.K.S.1
Rawdah, T.N.2
Olah, G.A.3
-
43
-
-
0343334875
-
-
Competing mechanisms are also suggested in a report on the chemistry of cinnamoyl chloride, see: Shotter, R. G.; Johnston, K. M.; Jones, J. F. Tetrahedron 1978, 34, 741.
-
(1978)
Tetrahedron
, vol.34
, pp. 741
-
-
Shotter, R.G.1
Johnston, K.M.2
Jones, J.F.3
|