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Volumn 73, Issue 16, 2008, Pages 6127-6136

Substituent effect on the efficiency of desulfurizative rearrangement of allylic disulfides

Author keywords

[No Author keywords available]

Indexed keywords

CCSD(T); CHEMICAL EQUATIONS; EFFECT OF SUBSTITUTION; FREE-ENERGY BARRIERS; FUNCTIONALIZATION; MILD CONDITIONS; RATE-LIMITING STEP; SIGMATROPIC REARRANGEMENTS; SUBSTITUENT EFFECTS;

EID: 50149089160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800747g     Document Type: Article
Times cited : (12)

References (63)
  • 11
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    • As illustrated by applications in dynamic combinatorial librairies, a
    • As illustrated by applications in dynamic combinatorial librairies. (a) Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. J. Am. Chem. Soc. 2000, 122, 12063.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 12063
    • Otto, S.1    Furlan, R.L.E.2    Sanders, J.K.M.3
  • 32
  • 46
    • 33847067864 scopus 로고    scopus 로고
    • We did not use the DFT methods (such as B3LYP) to calculate the free energy barrier because underestimation of the barriers of related reactions by the DFT methods was previously known. For examples, see: (a) Kinal, A, Piecuch, P. J. Phys. Chem. A 2007, 111, 734
    • We did not use the DFT methods (such as B3LYP) to calculate the free energy barrier because underestimation of the barriers of related reactions by the DFT methods was previously known. For examples, see: (a) Kinal, A.; Piecuch, P. J. Phys. Chem. A 2007, 111, 734.
  • 48
    • 27744489233 scopus 로고    scopus 로고
    • Problems of using MP2 to study pericyclic reactions were previously discussed. See: Ess, D. H.; Houk, K. N. J. Phys. Chem. A 2005, 109, 9542.
    • Problems of using MP2 to study pericyclic reactions were previously discussed. See: Ess, D. H.; Houk, K. N. J. Phys. Chem. A 2005, 109, 9542.
  • 50
    • 50149116975 scopus 로고    scopus 로고
    • Note: earlier studies by Hoefle and Baldwin on the equilibrium between alkyl allyl disulfides and thiosulfoxides indicated that increased bulk at R3 reduced the concentrations of the thiosulfoxides. See ref 24
    • 3 reduced the concentrations of the thiosulfoxides. See ref 24.
  • 62
    • 50149113894 scopus 로고    scopus 로고
    • Frisch, M. J, Tracks, 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, Bakken, V, 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, Keit
    • Frisch, M. J.; Tracks, 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.; Bakken, V.; 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 C.02; Gaussian, Inc.: Wallingford, CT, 2004.


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