Abstract
Rate determination and product studies have disclosed that the fragmentation pattern of radical cations 2-propenyl-1,4-dimethoxybenzene (1+ ·) and 2-propenyl-1,4,5-trimethoxybenzene (2+·) generated in one-electron oxidation of their parent substrates by 4-nitrobenzoyl peroxide (3) in CH3CN is greatly affected by ring-substitution status of the donor molecules. While ringbenzoloxylation (product 5) predominated in the reaction of dimethoxylated substrate (1), the oxidation of trimethoxylated donor 2 ended up with distonic radical cation mediated α,β-di-4-nitrobenzoloxylation as the major pathway.
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REFERENCES
A. Albini, M. Mella and M. Freccero, Tetrahedron 50, 575 (1994).
M. Schmittel and A. Burghart, Angrew. Chem. Int. Ed. Engl. 36, 2550 (1997).
(a) R. K. Haynes and S. C. Vonwiller, J. Chem. Soc. Chem. Commun. 451, (1990). (b) A. G. Griesbeck, J. Hirt, K. Peters, E.-M. Peters and H. G. Von Schnering, Chem. Eur. J. 2, 1388 (1996).
D. A. Evans, C. J. Dinsmore, D. A. Evrard and K. M. Devries, J. Am. Chem. Soc. 115, 6426 (1993).
E. Baciocchi, M. Mattioli and R. Romano, Acta Chem. Scand. 44, 645 (1990).
M. Mella, M. Fagnoni, M. Freccero, E. Fasani and A. Albini, Chem. Soc. Rev. 27, 81 (1998).
(a) S. Toji, S. Toki and S. Takamaku, J. Org. Chem. 56, 6240 (1991). (b) P. Chyongin, Pure Appl. Chem. 58, 1249 (1986).
(a) C. M. Husdon, M. R. Marzabadi, K. D. Moeller and D. G. New, J. Am. Chem. Soc. 113, 7372 (1991). (b) H. E. Zimmerman and K. D. Hofferacker, J. Org. Chem. 61, 5626 (1996).
T. Miyashi, H. Ikeda and Y. Takahashi, Acc. Chem. Res. 32, 815 (1999).
(a) L. J. Johnston and N. P. Schepp, J. Am. Chem. Soc. 115, 6564 (1993). (b) Ibid. Pure Appl. Chem. 67, 71 (1995). (c) M. S. Workentin, N. P. Schepp, L. J. Johnston and D. D. Wayer, J. Am. Chem. Soc. 116, 1141 (1994).
C. Walling and C.-X. Zhao, Tetrahedron 38, 1105 (1982).
C.-X. Zhao, G. M. Ei-Taliawi and C. Walling, J. Org. Chem. 48, 4908 (1983).
X.-K. Jiang, C.-X. Zhao and Y.-F. Gong, J. Phys. Org. Chem. 4, 1 (1991).
C.-X. Zhao, Y.-F. Gong, H.-Y. He and X.-K. Jiang, J. Phys. Org. Chem. 12, 688 (1999).
Landolt-Bronstein, in: Radical Reaction Rates in Liquid, Vol. 13d, p. 127. Springer, Berlin, Heidelberg, New York, Tokyo (1987).
C. G. Swain, W. H. Stockmeyer and J. T. Clarke, J. Am. Chem. Soc. 72, 5426 (1950).
C.-X. Zhao, R.-M. Zhou, H.-Q. Pan, X.-S. Jin, Y.-L. Qu, C.-J. Wu and X.-K. Jiang, J. Org. Chem. 47, 2009 (1982).
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Zhao, Y., Li, W., Chen, QY. et al. How radical cations react? - Distonic radical cation mediated α(nucleophilic), β(radical)-dibenzoloxylation of donor ArCH = CHR. Research on Chemical Intermediates 27, 287–296 (2001). https://doi.org/10.1163/156856701300356509
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DOI: https://doi.org/10.1163/156856701300356509