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Volumn 128, Issue 24, 2006, Pages 7782-7795

Mechanism of the diphenyldisulfone-catalyzed isomerization of alkenes. Origin of the chemoselectivity: Experimental and quantum chemistry studies

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; IONIZATION; ISOMERIZATION; ORGANIC COMPOUNDS; QUANTUM THEORY; REACTION KINETICS;

EID: 33745406036     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0579210     Document Type: Article
Times cited : (28)

References (150)
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    • For reviews on protection and deprotection of alcohols, see: (a) Kocieñski, P. J. In Protecting Groups; Enders, D., Noyori, R., Trost, B. M., Eds.; Thieme Verlag: Stuttgart, 1994.
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  • 26
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    • Guibé, F.1
  • 33
    • 33745363002 scopus 로고    scopus 로고
    • note
    • This mechanism is also compatible with inhibition by radical scavenging agents; the latter inhibit the combination of two sulfinyl radicals.
  • 36
    • 9444256828 scopus 로고
    • (b) Lee, K. H. Tetrahedron 1970, 26, 1503-1507.
    • (1970) Tetrahedron , vol.26 , pp. 1503-1507
    • Lee, K.H.1
  • 41
    • 0002649686 scopus 로고
    • Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Willey & Sons: Ltd. Chichester; Chapter 25
    • (g) Chatgilialoglu, C. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Willey & Sons: Ltd. Chichester, 1988; Chapter 25, pp 1089-1113.
    • (1988) The Chemistry of Sulphones and Sulphoxides , pp. 1089-1113
    • Chatgilialoglu, C.1
  • 46
    • 33745427658 scopus 로고    scopus 로고
    • note
    • - pair.
  • 82
    • 33745360412 scopus 로고    scopus 로고
    • note
    • 34 With our solid polysulfone PS Front-strain and Back-strain are expected to lower the barriers of the C-S(sulfone) and C-O(sulfinate) homolyses, and highly positive entropies of dissociation are expected for the C-O bond leakage of sulfinates with high molecular mass.
  • 85
    • 0000535864 scopus 로고
    • (c) Mackle, H. Tetrahedron 1963, 19, 1159-1170.
    • (1963) Tetrahedron , vol.19 , pp. 1159-1170
    • Mackle, H.1
  • 96
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    • and references cited therein
    • (d) Getty, J. D.; Liu, X.; Kelly, P. B. J. Chem. Phys. 1996, 104, 3176-3180 and references cited therein.
    • (1996) J. Chem. Phys. , vol.104 , pp. 3176-3180
    • Getty, J.D.1    Liu, X.2    Kelly, P.B.3
  • 99
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    • Concurrent hydrolysis of diphenyldisulfone occurred under these conditions, thus leading to incomplete isomerization of the alkene, unless more diphenyldisulfone would be added to the reaction mixture. For the hydrolysis of diphenyldisulfone, see: Kice, J. L.; Margolis, H. C.; Johnson, W. C.; Wulff, C. A. J. Org. Chem. 1977, 43, 2933-2935.
    • (1977) J. Org. Chem. , vol.43 , pp. 2933-2935
    • Kice, J.L.1    Margolis, H.C.2    Johnson, W.C.3    Wulff, C.A.4
  • 123
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    • Bertrán, J.; Csizmadia, I. G. Eds.; NATO ASI Series, Kluwer Academic Publishers: Dordrecht
    • (c) Shaik, S. S. In New Theoretical Concepts for Understanding Organic Reactions; Bertrán, J.; Csizmadia, I. G. Eds.; NATO ASI Series, Kluwer Academic Publishers: Dordrecht, 1988.
    • (1988) New Theoretical Concepts for Understanding Organic Reactions
    • Shaik, S.S.1
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    • Kochi, J. K., Ed.; Wiley: New York
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    • Russell, G.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.