-
1
-
-
0003497661
-
-
Metzger. J. V., Ed.; Wiley & Sons: New York.
-
Thiazole and its Derivatives; Metzger. J. V., Ed.; Wiley & Sons: New York. 1979.
-
(1979)
Thiazole and Its Derivatives
-
-
-
2
-
-
84918117445
-
-
Takeda Chem. Ind., Ltd. Fr. Patent 1,400,843, 1965
-
Takeda Chem. Ind., Ltd. Fr. Patent 1,400,843, 1965; Chem. Abstr. 1965, 63, 9922.
-
(1965)
Chem. Abstr.
, vol.63
, pp. 9922
-
-
-
3
-
-
85042925168
-
-
(a) Jacobi, P. A.; Weiss, K. T.; Egberson, M. Heterocycles 1984, 22, 281-286.
-
(1984)
Heterocycles
, vol.22
, pp. 281-286
-
-
Jacobi, P.A.1
Weiss, K.T.2
Egberson, M.3
-
4
-
-
0000922322
-
-
(b) Jacobi, P. A.; Egbertson, M.; Frechette, R. F.; Miso, C. K.; Weiss, K. T. Tetrahedron 1988, 44, 3327-3338.
-
(1988)
Tetrahedron
, vol.44
, pp. 3327-3338
-
-
Jacobi, P.A.1
Egbertson, M.2
Frechette, R.F.3
Miso, C.K.4
Weiss, K.T.5
-
8
-
-
37049139457
-
-
(a) Abbott, P. J.; Acheson, R. M.; Eisner, U.; Watkin, D. J.; Carruthers, J. R. J. Chem. Soc., Chem. Commun. 1975, 155-156.
-
(1975)
J. Chem. Soc., Chem. Commun.
, pp. 155-156
-
-
Abbott, P.J.1
Acheson, R.M.2
Eisner, U.3
Watkin, D.J.4
Carruthers, J.R.5
-
9
-
-
51149202743
-
-
(b) Abbott, P. J.; Acheson, R. M.; Eisner, U.; Watkin, D. J.; Carruthers, J. R. J. Chem. Soc., Perkin Trans, 1 1976, 1269-1278.
-
(1976)
J. Chem. Soc., Perkin Trans. 1
, pp. 1269-1278
-
-
Abbott, P.J.1
Acheson, R.M.2
Eisner, U.3
Watkin, D.J.4
Carruthers, J.R.5
-
11
-
-
0000015271
-
-
(a) Dondoni, A.; Medici, A.; Venturoli, C. J. Org. Chem. 1980, 45, 621-626.
-
(1980)
J. Org. Chem.
, vol.45
, pp. 621-626
-
-
Dondoni, A.1
Medici, A.2
Venturoli, C.3
-
12
-
-
0000985432
-
-
(b) Medici, A.; Pedrini, P.; Venturoli, C.; Dondoni, A. J. Org. Chem. 1981, 46, 2790-2793.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 2790-2793
-
-
Medici, A.1
Pedrini, P.2
Venturoli, C.3
Dondoni, A.4
-
13
-
-
0022367591
-
-
The adduct 4 was isolated along with other secondary products from the reaction of the amino functionality with the acetylenic ester. See: Crank, G.; Khan, H. R. J. Heterocycl. Chem. 1985, 22, 1281-1284.
-
(1985)
J. Heterocycl. Chem.
, vol.22
, pp. 1281-1284
-
-
Crank, G.1
Khan, H.R.2
-
14
-
-
84985624860
-
-
Gompper, R.; Heinemann, U. Angew. Chem., Int. Ed. Engl. 1980, 19, 217.
-
(1980)
Angew. Chem., Int. Ed. Engl.
, vol.19
, pp. 217
-
-
Gompper, R.1
Heinemann, U.2
-
15
-
-
0030598057
-
-
Morel, G.; Marchand, E.; Pradère, J.-P.; Toupet, L.; Sinbandhit, S. Tetrahedron 1996, 52, 10095-10112.
-
(1996)
Tetrahedron
, vol.52
, pp. 10095-10112
-
-
Morel, G.1
Marchand, E.2
Pradère, J.-P.3
Toupet, L.4
Sinbandhit, S.5
-
17
-
-
0000951101
-
-
Reinhoudt, D. N.; Verboom, W.; Visser, G. W.; Trompenaars, W. P.; Harkema, S.; van Hummel, G. J. J. Am. Chem. Soc. 1984, 106, 1341-1350.
-
(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 1341-1350
-
-
Reinhoudt, D.N.1
Verboom, W.2
Visser, G.W.3
Trompenaars, W.P.4
Harkema, S.5
Van Hummel, G.J.6
-
18
-
-
33748960439
-
-
Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708.
-
(1992)
Angew. Chem., Int. Ed. Engl.
, vol.31
, pp. 682-708
-
-
Houk, K.N.1
Li, Y.2
Evanseck, J.D.3
-
19
-
-
1842437209
-
-
Epiotis, N. D.; Yates, R. L.; Carlberg, D.; Bernardi, F. J. Am. Chem. Soc. 1976, 98, 453-461.
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 453-461
-
-
Epiotis, N.D.1
Yates, R.L.2
Carlberg, D.3
Bernardi, F.4
-
21
-
-
84984214670
-
-
Hoffmann, R. W.; Bressel, U.; Gehlhaus, J.; Häuser, H. Chem. Ber. 1971, 104, 873-885.
-
(1971)
Chem. Ber.
, vol.104
, pp. 873-885
-
-
Hoffmann, R.W.1
Bressel, U.2
Gehlhaus, J.3
Häuser, H.4
-
24
-
-
0000566875
-
-
(a) Huebner, C. F.; Dorfman, L.; Robison, M. M.; Donoghue, E.; Pierson, W. G.; Strachan, P. J. Org. Chem. 1963, 28, 3134-3140.
-
(1963)
J. Org. Chem.
, vol.28
, pp. 3134-3140
-
-
Huebner, C.F.1
Dorfman, L.2
Robison, M.M.3
Donoghue, E.4
Pierson, W.G.5
Strachan, P.6
-
26
-
-
0001714545
-
-
(c) Snider, B. B.; Rodini, D. J.; Conn, R. S. E.; Sealfon, S. J. Am. Chem. Soc. 1979, 101, 5283-5293.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 5283-5293
-
-
Snider, B.B.1
Rodini, D.J.2
Conn, R.S.E.3
Sealfon, S.4
-
31
-
-
0040460902
-
-
(d) Verboom, W.; Visser, G. W.; Trompenaars, W. P.; Reinhoudt, D. N. Tetrahedron 1981, 37, 3525-3533.
-
(1981)
Tetrahedron
, vol.37
, pp. 3525-3533
-
-
Verboom, W.1
Visser, G.W.2
Trompenaars, W.P.3
Reinhoudt, D.N.4
-
32
-
-
0000067476
-
-
(e) Reinhoudt, D. N.; Geevers, J.; Trompenaars, W. P. J. Org. Chem. 1981, 46, 424-434.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 424-434
-
-
Reinhoudt, D.N.1
Geevers, J.2
Trompenaars, W.P.3
-
36
-
-
0028889349
-
-
(d) Temciuc, E.; Hörnfeldt, A.-B.; Gronowitz, S.; Stâlhandske, C. Tetrahedron 1995, 51, 13185-13196.
-
(1995)
Tetrahedron
, vol.51
, pp. 13185-13196
-
-
Temciuc, E.1
Hörnfeldt, A.-B.2
Gronowitz, S.3
Stâlhandske, C.4
-
37
-
-
0000819798
-
-
Brannock, K. C.; Burpitt, R. D.; Goodlett, V. W.; Thweatt, J. G. J. Org. Chem. 1963, 28, 1464-1468.
-
(1963)
J. Org. Chem.
, vol.28
, pp. 1464-1468
-
-
Brannock, K.C.1
Burpitt, R.D.2
Goodlett, V.W.3
Thweatt, J.G.4
-
39
-
-
84962466172
-
-
note
-
These protons appear in the range of 5.95-6.68 ppm and, thus, at lower frequencies compared to the chemical shift of this proton in the thiazole ring (7.41 ppm).
-
-
-
-
40
-
-
37049126518
-
-
The participation of dipolar intermediates in some of these reactions is supported by the high yields of fumarates obtained when the reaction is conducted in methanol, where a proton is available to quench the zwitterion. See: Acheson, R. M.; Brisdon, J. N.; Cameron, T. S. J. Chem. Soc., Perkin Trans. 1 1972, 968-975.
-
(1972)
J. Chem. Soc., Perkin Trans. 1
, pp. 968-975
-
-
Acheson, R.M.1
Brisdon, J.N.2
Cameron, T.S.3
-
41
-
-
0001739662
-
-
The reaction pathway to give the diastereomeric compounds 15 may involve the formation of the bent dipole 14g, which can easily equilibrate with 14g″ through the cumulenic 14g′. The (E)- and (Z)-15 adducts should be formed by migration of the hydrogen of the former C5 of the thiazole in 14g and 14g″ or, alternatively, from the allenic structure 16 by a tautomeric equilibrium. See: (a) Caramella, P.; Houk, K. N. Tetrahedron Lett. 1981, 22, 819-822.
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 819-822
-
-
Caramella, P.1
Houk, K.N.2
-
42
-
-
33745708707
-
-
Patai, S., Ed.; Wiley: New York. (Equation Presented)
-
(b) Dickstein, J. I.; Miller, S. I. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; pp 819-826. (Equation Presented)
-
(1978)
The Chemistry of the Carbon-Carbon Triple Bond
, pp. 819-826
-
-
Dickstein, J.I.1
Miller, S.I.2
-
46
-
-
33745694624
-
-
Müller, E., Ed.; G. Thieme Verlag: Stuttgart
-
(b) Seebach, D. In Houben-Weyl, Methoden der organischen Chemie; Müller, E., Ed.; G. Thieme Verlag: Stuttgart. 1971; Vol. IV/4, pp 418-419.
-
(1971)
Houben-Weyl, Methoden der Organischen Chemie
, vol.4
, Issue.4
, pp. 418-419
-
-
Seebach, D.1
-
47
-
-
84962462270
-
-
Patent WO2005097797, 2005
-
See, for example: (a) Di Cesare, M. A.; Campiani, G.; Butini, S. Patent WO2005097797, 2005; Chem. Abstr. 2005, 143, 405933.
-
(2005)
Chem. Abstr.
, vol.143
, pp. 405933
-
-
Di Cesare, M.A.1
Campiani, G.2
Butini, S.3
-
51
-
-
84985561524
-
-
(a) Yamamoto, K.; Yamazaki, S.; Osedo, H.; Murata, I. Angew. Chem., Int. Ed. Engl. 1986, 25, 635-637.
-
(1986)
Angew. Chem., Int. Ed. Engl.
, vol.25
, pp. 635-637
-
-
Yamamoto, K.1
Yamazaki, S.2
Osedo, H.3
Murata, I.4
-
53
-
-
0035973761
-
-
Cabarrocas, G.; Ventura, M.; Maestro, M.; Mahía, J.; Villalgordo, J. M. Tetrahedron: Asymmetry 2001, 12, 1851-1863.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 1851-1863
-
-
Cabarrocas, G.1
Ventura, M.2
Maestro, M.3
Mahía, J.4
Villalgordo, J.M.5
-
54
-
-
0032509454
-
-
Domingo, L. R.; Picher, M. T.; Zaragoza, R. J. J. Org. Chem. 1998, 63, 9183-9189.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 9183-9189
-
-
Domingo, L.R.1
Picher, M.T.2
Zaragoza, R.J.3
-
55
-
-
0000489268
-
-
(a) Domingo, L. R.; Picher, M. T.; Aurell, M. J. J. Phys. Chem. A 1999, 103, 11425-11430.
-
(1999)
J. Phys. Chem. A
, vol.103
, pp. 11425-11430
-
-
Domingo, L.R.1
Picher, M.T.2
Aurell, M.J.3
-
56
-
-
0034595837
-
-
(b) Domingo, L. R.; Picher, M. T.; Andres, J. J. Org. Chem. 2000, 65, 3473-3477.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 3473-3477
-
-
Domingo, L.R.1
Picher, M.T.2
Andres, J.3
-
57
-
-
0030597005
-
-
Cobo, J.; Melguizo, M.; Nogueras, M.; Sánchez, A.; Dobado, J. A.; Nonella, M. Tetrahedron 1996, 52, 13721-13732.
-
(1996)
Tetrahedron
, vol.52
, pp. 13721-13732
-
-
Cobo, J.1
Melguizo, M.2
Nogueras, M.3
Sánchez, A.4
Dobado, J.A.5
Nonella, M.6
-
58
-
-
0001367502
-
-
(a) Gleiter, R.; Krennich, G.; Cremer, D.; Yamamoto, K.; Murata, I. J. Am. Chem. Soc. 1985, 107, 6874-6879.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 6874-6879
-
-
Gleiter, R.1
Krennich, G.2
Cremer, D.3
Yamamoto, K.4
Murata, I.5
-
59
-
-
0000368482
-
-
(b) Miller, K. J.; Moschner, K. F.; Potts, K. T. J. Am. Chem. Soc. 1983, 105, 1705-1712.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 1705-1712
-
-
Miller, K.J.1
Moschner, K.F.2
Potts, K.T.3
-
60
-
-
0037955548
-
-
Lee, P. S.; Sakai, S.; Hörsteman, P.; Roth, W. R.; Kallel, E. A.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 5839-5848.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 5839-5848
-
-
Lee, P.S.1
Sakai, S.2
Hörsteman, P.3
Roth, W.R.4
Kallel, E.A.5
Houk, K.N.6
-
61
-
-
0000092866
-
-
(a) Chapman, O. L.; Pasto, D. J.; Borden, G. W.; Griswold, A. A. J. Am. Chem. Soc. 1962, 84, 1220-1224.
-
(1962)
J. Am. Chem. Soc.
, vol.84
, pp. 1220-1224
-
-
Chapman, O.L.1
Pasto, D.J.2
Borden, G.W.3
Griswold, A.A.4
-
62
-
-
0342795759
-
-
(b) Breslow, R.; Napierski, J.; Schmidt, A. H. J. Am. Chem. Soc. 1972, 94, 5906-5907.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 5906-5907
-
-
Breslow, R.1
Napierski, J.2
Schmidt, A.H.3
-
64
-
-
0002728853
-
-
Equation Presented
-
Reinhoudt has also proposed (see ref 21b) that the ring opening of thiabicyclo[3.2.0]hepta-3,6-dienes leading to the corresponding thiepines can be regarded as an electrocyclic symmetry-allowed disrotatory reaction of the dihydrothiophene ring analogous to that occurring in the isoelectronic bicyclo[4.2.0]octatriene which isomerizes rapidly to cyclooctatetraene. See: Glass, D. S.; Watthey, J. W. H.; Winstein, S. Tetrahedron Lett. 1965, 377-383. (Equation Presented)
-
(1965)
Tetrahedron Lett.
, pp. 377-383
-
-
Glass, D.S.1
Watthey, J.W.H.2
Winstein, S.3
-
69
-
-
1542508210
-
-
Kharash, N., Ed.; Pergamon Press: New York
-
(b) Loudon, J. D. In Organic Sulfur Compounds; Kharash, N., Ed.; Pergamon Press: New York, 1961, pp 299-305.
-
(1961)
Organic Sulfur Compounds
, pp. 299-305
-
-
Loudon, J.D.1
-
70
-
-
0001457570
-
-
Yamamoto, K.; Yamakazi, S.; Kohashi, Y.; Murata, I. Tetrahedron Lett. 1982, 23, 3195-3198.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 3195-3198
-
-
Yamamoto, K.1
Yamakazi, S.2
Kohashi, Y.3
Murata, I.4
-
71
-
-
84962466159
-
-
note
-
This value indicates that the C12 carbon atom presents an sp hybridization where the charge located at this center occupies a p atomic orbital. A similar value has been found in the transition state corresponding to the configuration inversion connecting two polar intermediates coming from the reaction of DMAD with 1-methylpyrrole (see ref 34).
-
-
-
-
72
-
-
84986492429
-
-
In fact, INT is slightly higher in energy than TS2, probably as consequence of using the approximation of frozen geometries. See: (a) Bonaccorsi, R.; Cammi, R.; Tomasi, J. J. Comput. Chem. 1991, 12, 301-309.
-
(1991)
J. Comput. Chem.
, vol.12
, pp. 301-309
-
-
Bonaccorsi, R.1
Cammi, R.2
Tomasi, J.3
-
75
-
-
33745694620
-
-
Birkinshaw, T. N.; Meakins, G. D.; Plackett, S. J. J. Chem. Soc., Perkin Trans. 1 1988, 2209-2212.
-
(1988)
J. Chem. Soc., Perkin Trans. 1
, pp. 2209-2212
-
-
Birkinshaw, T.N.1
Meakins, G.D.2
Plackett, S.J.3
-
76
-
-
0141704726
-
-
Gaussian, Inc.: Pittsburgh, PA
-
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
-
(2003)
Gaussian 03, Revision B.03
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Adamo, C.36
Jaramillo, J.37
Gomperts, R.38
Stratmann, R.E.39
Yazyev, O.40
Austin, A.J.41
Cammi, R.42
Pomelli, C.43
Ochterski, J.W.44
Ayala, P.Y.45
Morokuma, K.46
Voth, G.A.47
Salvador, P.48
Dannenberg, J.J.49
Zakrzewski, V.G.50
Dapprich, S.51
Daniels, A.D.52
Strain, M.C.53
Farkas, O.54
Malick, D.K.55
Rabuck, A.D.56
Raghavachari, K.57
Foresman, J.B.58
Ortiz, J.V.59
Cui, Q.60
Baboul, A.G.61
Clifford, S.62
Cioslowski, J.63
Stefanov, B.B.64
Liu, G.65
Liashenko, A.66
Piskorz, P.67
Komaromi, I.68
Martin, R.L.69
Fox, D.J.70
Keith, T.71
Al-Laham, M.A.72
Peng, C.Y.73
Nanayakkara, A.74
Challacombe, M.75
Gill, P.M.W.76
Johnson, B.77
Chen, W.78
Wong, M.W.79
Gonzalez, C.80
Pople, J.A.81
more..
-
77
-
-
84873055189
-
-
Wiley: New York; and references therein
-
Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. In Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 71-82 and references therein.
-
(1986)
Ab Initio Molecular Orbital Theory
, pp. 71-82
-
-
Hehre, W.J.1
Radom, L.2
Schleyer, P.V.R.3
Pople, J.A.4
-
79
-
-
0001192473
-
-
Lipkowitz, K. B., Boyds, D. B., Eds.; VCH Publishers: New York
-
(b) Bartolotti, L. J.; Fluchichk, K. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyds, D. B., Eds.; VCH Publishers: New York, 1996; Vol. 7, pp 187-216.
-
(1996)
Reviews in Computational Chemistry
, vol.7
, pp. 187-216
-
-
Bartolotti, L.J.1
Fluchichk, K.2
-
80
-
-
0030218597
-
-
(c) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980.
-
(1996)
J. Phys. Chem.
, vol.100
, pp. 12974-12980
-
-
Kohn, W.1
Becke, A.D.2
Parr, R.G.3
-
81
-
-
0344791553
-
-
(d) Ziegler, T. Chem. Rev. 1991, 91, 651-667.
-
(1991)
Chem. Rev.
, vol.91
, pp. 651-667
-
-
Ziegler, T.1
-
86
-
-
84961981991
-
-
(c) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
-
(1997)
J. Chem. Phys.
, vol.107
, pp. 3210-3221
-
-
Barone, V.1
Cossi, M.2
Tomasi, J.3
-
87
-
-
36148995600
-
-
(a) Redd, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
-
(1985)
J. Chem. Phys.
, vol.83
, pp. 735-746
-
-
Redd, A.E.1
Weinstock, R.B.2
Weinhold, F.3
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