Catalysis by Cucurbituril. The Significance of Bound-Substrate Destabilization for Induced Triazole Formation

Journal of Organic Chemistry

Volumn 54, Issue 22, 1989, Pages 5302-5308

  Mock, William L ^a   Irra, Ted A ^a   Wepsiec, James P ^a   Adhya, Mita ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001333572     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00283a024     Document Type: Article

References (15)

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6. Mock, W. L.; Shih, N. Y. J. Org. Chem. 1986, 51, 4440. Mock, W. L.; Shih, N. Y. J. Am. Chem. Soc. 1988, 110, 4706.
7. Preliminary communication: Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3619.
8. Huisgen, R.; Szeimies, G.; Moebius, L. Chem. Ber. 1967, 100, 2494. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, p 1. Also see Lwowski, W. p 559.
9. Mock, W. L.; Shih, N. Y. J. Am. Chem. Soc. 1989, 111, 2697.
10. Product release as the rate-limiting step in enzymic reactions is a common phenomenon: Cleland, W. W. Acc. Chem. Res. 1975, 8, 145.
11. Schill, G. Catenaries, Rotaxanes and Knots; Academic: New York, 1971.
12. For a number of 1,3-dipolar cycloaddition reactions a large negative volume of activation (AV* ca. -20 cm3 M-1has been observed: Yoshimura, Y.; Osugi, J.; Nakahara, M. Bull. Chem. Soc. Jpn. 1983, 56, 680. Yoshimura, Y.; Osugi, J.; Nakahara, M. J. Am. Chem. Soc. 1983, 105, 5414. Swieton, G.; Jouanne, J. v.; Kelm, H.; Huisgen, R. J. Org. Chem. 1983, 48, 1035. This is further discussed in ref 8.
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