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Volumn 118, Issue 12, 1996, Pages 2872-2881

Reactivity of radical cations. Effect of radical cation and alkene structure on the absolute rate constants of radical cation mediated cycloaddition reactions

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EID: 0011227940     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9535468     Document Type: Article
Times cited : (100)

References (55)
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    • A number of examples of the synthetic utility of alkene radical cation cycloadditions are available: Wilson, R. M.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. J. Am. Chem. Soc. 1989, 111, 1749-1754. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828. Mattay, J. Synthesis 1989, 233-252. Schmittel. M.; von Seggern, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 999-1001. Gieseler, A.; Steckhan. E.; Wiest, O., Knoch, F. J. Org. Chem. 1991, 56, 1405-1411. Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Kruger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358-10359. Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901-903. Arnold, D R ; McManus, K. A.; Du, X. Can J. Chem. 1994, 72, 415-429. Connor, D. A.; Arnold, D. R.; Bakshi, P. K.; Cameron, T. S. Can. J. Chem. 1995, 73, 762-771.
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    • A number of examples of the synthetic utility of alkene radical cation cycloadditions are available: Wilson, R. M.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. J. Am. Chem. Soc. 1989, 111, 1749-1754. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828. Mattay, J. Synthesis 1989, 233-252. Schmittel. M.; von Seggern, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 999-1001. Gieseler, A.; Steckhan. E.; Wiest, O., Knoch, F. J. Org. Chem. 1991, 56, 1405-1411. Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Kruger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358-10359. Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901-903. Arnold, D R ; McManus, K. A.; Du, X. Can J. Chem. 1994, 72, 415-429. Connor, D. A.; Arnold, D. R.; Bakshi, P. K.; Cameron, T. S. Can. J. Chem. 1995, 73, 762-771.
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    • A number of examples of the synthetic utility of alkene radical cation cycloadditions are available: Wilson, R. M.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. J. Am. Chem. Soc. 1989, 111, 1749-1754. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828. Mattay, J. Synthesis 1989, 233-252. Schmittel. M.; von Seggern, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 999-1001. Gieseler, A.; Steckhan. E.; Wiest, O., Knoch, F. J. Org. Chem. 1991, 56, 1405-1411. Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Kruger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358-10359. Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901-903. Arnold, D R ; McManus, K. A.; Du, X. Can J. Chem. 1994, 72, 415-429. Connor, D. A.; Arnold, D. R.; Bakshi, P. K.; Cameron, T. S. Can. J. Chem. 1995, 73, 762-771.
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    • Hoffmann, U.1    Gao, Y.2    Pandey, B.3    Klinge, S.4    Warzecha, K.-D.5    Kruger, C.6    Roth, H.D.7    Demuth, M.8
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    • A number of examples of the synthetic utility of alkene radical cation cycloadditions are available: Wilson, R. M.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. J. Am. Chem. Soc. 1989, 111, 1749-1754. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828. Mattay, J. Synthesis 1989, 233-252. Schmittel. M.; von Seggern, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 999-1001. Gieseler, A.; Steckhan. E.; Wiest, O., Knoch, F. J. Org. Chem. 1991, 56, 1405-1411. Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Kruger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358-10359. Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901-903. Arnold, D R ; McManus, K. A.; Du, X. Can J. Chem. 1994, 72, 415-429. Connor, D. A.; Arnold, D. R.; Bakshi, P. K.; Cameron, T. S. Can. J. Chem. 1995, 73, 762-771.
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  • 15
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    • A number of examples of the synthetic utility of alkene radical cation cycloadditions are available: Wilson, R. M.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. J. Am. Chem. Soc. 1989, 111, 1749-1754. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828. Mattay, J. Synthesis 1989, 233-252. Schmittel. M.; von Seggern, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 999-1001. Gieseler, A.; Steckhan. E.; Wiest, O., Knoch, F. J. Org. Chem. 1991, 56, 1405-1411. Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Kruger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358-10359. Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901-903. Arnold, D R ; McManus, K. A.; Du, X. Can J. Chem. 1994, 72, 415-429. Connor, D. A.; Arnold, D. R.; Bakshi, P. K.; Cameron, T. S. Can. J. Chem. 1995, 73, 762-771.
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    • A number of examples of the synthetic utility of alkene radical cation cycloadditions are available: Wilson, R. M.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. J. Am. Chem. Soc. 1989, 111, 1749-1754. Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828. Mattay, J. Synthesis 1989, 233-252. Schmittel. M.; von Seggern, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 999-1001. Gieseler, A.; Steckhan. E.; Wiest, O., Knoch, F. J. Org. Chem. 1991, 56, 1405-1411. Hoffmann, U.; Gao, Y.; Pandey, B.; Klinge, S.; Warzecha, K.-D.; Kruger, C.; Roth, H. D.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 10358-10359. Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901-903. Arnold, D R ; McManus, K. A.; Du, X. Can J. Chem. 1994, 72, 415-429. Connor, D. A.; Arnold, D. R.; Bakshi, P. K.; Cameron, T. S. Can. J. Chem. 1995, 73, 762-771.
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    • note
    • A range of values for the various parameters in eq 4 have been used to calculate the electron transfer rate constant, without improving the fit of the calculated and observed rate constants.


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