Photochemical nitration by tetranitromethane. Part XL. Regiochemistry of trinitromethyl attachment in the photolysis of benzofuran with tetranitromethane

Acta Chemica Scandinavica

Volumn 51, Issue 10, 1997, Pages 984-999

  Butts, Craig P ^a   Eberson, Lennart ^b   Gonzáles Luque, Remedios ^c   Hartshorn, Chris M ^a   Hartshorn, Michael P ^a   Merchán, Manuela ^c   Robinson, Ward T ^a   Roos, Björn O ^b   Vallance, Claire ^a   Wood, Bryan R ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b LUND UNIVERSITY   (Sweden)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042499514     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.51-0984     Document Type: Article

References (43)

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3. Eberson, L., Hartshorn, M. P. and Radner, F. In Coxon, J. M., Ed., Advances in Carbocation Chemistry, Vol. 2, JAI Press, London 1995, p. 207; Eberson, L., Hartshorn, M. P. and Radner, F. Acta Chem. Scand. 48 (1994) 937.
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7. Eberson, L., Hartshorn, M. P., Radner, F. and Svensson, J. O. Acta Chem. Scand 50 (1996) 885; Butts, C. P., Eberson, L., Hartshorn, M. P. and Persson, O. Acta Chem. Scand. 51 (1997) 718.
8. For reviews on radical cations: Bard, A. J., Ledwith, A. and Shine, H. J. Adv. Phys. Org. Chem. 13 (1976) 156; Hammerich, O. and Parker, V. D. Adv. Phys. Org. Chem. 20 (1984) 55.
9. For reviews on radical cations: Bard, A. J., Ledwith, A. and Shine, H. J. Adv. Phys. Org. Chem. 13 (1976) 156; Hammerich, O. and Parker, V. D. Adv. Phys. Org. Chem. 20 (1984) 55.
10. Eberson, L., González-Luque, R., Merchán, M., Radner, F., Roos, B. O. and Shaik, S. J. Chem. Soc., Perkin Trans. 2 (1997) 463.
11. The choice of non-alternant systems was partly dictated by the fact that the radical ions of such systems do not obey the pairing theorem (Dewar, M. J. S. and Dougherty, R. C. The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975, p. 75). Thus the regiochemistry of nucleophile (or radical) attack upon radical cations is expected to show synthetically significant differences from those of the corresponding substrate-electrophile reactions. For alternant systems, no such differences are expected.
12. (a) Butts, C. P., Eberson, L., Hartshorn, M. P., Robinson, W. T. and Wood, B. R. Acta Chem. Scand. 50 (1996) 587;
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20. Shaik, S. S. J. Am. Chem. Soc. 103 (1982) 3692; Pross, A. Adv. Phys Org. Chem. 21 (1985) 99; Shaik, S. S. Progr. Phys. Org. Chem. 15 (1985) 197; Pross, A. and Shaik, S. S. Acc. Chem. Res. 110 (1983) 3537; Shaik, S. S. and Pross, A. J. Am. Chem. Soc. 111 (1989) 4306; Shaik, S. S. and Dinnocenzo, J. P. J. Org. Chem. 55 (1990) 3434; Shaik, S., Reddy, A. C., Ioffe, A., Dinnocenzo, J. P., Danovich, D. and Cho, J. K. J. Am. Chem. Soc. 117 (1995) 3205.
21. Shaik, S. S. J. Am. Chem. Soc. 103 (1982) 3692; Pross, A. Adv. Phys Org. Chem. 21 (1985) 99; Shaik, S. S. Progr. Phys. Org. Chem. 15 (1985) 197; Pross, A. and Shaik, S. S. Acc. Chem. Res. 110 (1983) 3537; Shaik, S. S. and Pross, A. J. Am. Chem. Soc. 111 (1989) 4306; Shaik, S. S. and Dinnocenzo, J. P. J. Org. Chem. 55 (1990) 3434; Shaik, S., Reddy, A. C., Ioffe, A., Dinnocenzo, J. P., Danovich, D. and Cho, J. K. J. Am. Chem. Soc. 117 (1995) 3205.
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