Abstract
Sulfonyl radicals generated by the oxidation of sodium arylsulfinates with cerium(IV) ammonium nitrate (CAN) undergo addition reaction with styrenes to give the sulfonylated products in good yields.
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REFERENCES
N. S. Simpkins, Sulfones in Organic Synthesis. Pergamon Press, Oxford (1993).
W. E. Truce and G. C. Wolf, J. Org. Chem. 36, 1727 (1971).
M. S. Kharasch and R. A. Mosher, J. Org. Chem. 17, 453 (1952).
L. K. Liu, Y. Chi and K.-Y. Jen, J. Org. Chem. 45, 406 (1980).
T. G. Back and S. Collins, J. Org. Chem. 46, 3249 (1981).
R. A. Gancarz and J. L. Kice, J. Org. Chem. 46, 4899 (1981).
K. Narasaka, T. Mochizuki and S. Hayakawa, Chem Lett. 1705 (1994).
T. Mochizuki, S. Hayakawa and K. Narasaka, Bull. Chem. Soc. Jpn. 69, 2317 (1996).
W. S. Trahanovsky and M. D. Robbins, J. Am. Chem. Soc. 93, 5256 (1971).
R. U. Lemieux and R. M. Ratcliffe, Can. J. Chem. 93, 5256 (1979).
V. Nair and L. G. Nair, Tetrahedron Lett. 39, 4585 (1998).
V. Nair, T. G. George, L. G. Nair and S. B. Panicker, Tetrahedron Lett. 40, 1105 (1999).
V. Nair and T. G. George, Tetrahedron Lett. 41, 3199 (2000).
V. Nair, L. G. Nair, T. G. George and A. Augustine, Tetrahedron 56, 7607 (2000).
V. Nair, T. G. George, V. Sheeba, A. Augustine, L. Balagopal and L. G. Nair, Synlett, 1597 (2000).
V. Nair, A. Augustine, T. G. George and L. G. Nair, Tetrahedron Lett. 42, 6763 (2001).
K. Narasaka, T. Mochizuki and S. Hayakawa, Chem. Lett. 1705 (1994).
T. Mochizuki, S. Hayakawa and K. Narasaka, Bull. Chem. Soc. Jpn. 69, 2517 (1996).
M. C. Clasby and D. Craig, Synlett 825 (1992).
R. A. Gancarz and J. L. Kice, J. Org. Chem. 46, 4899 (1981).
D. H. Duan and X. Huang, Synlett, 3 (1999).
D. H. Duan and X. Huang, Synlett, 317 (1999).
W. B. Jang, H. J. Jeon and D. Y. Oh, Synth. Commun. 28, 1253 (1998).
W. J. Lee, C.-W. Lee, J. H. Jung and D. Y. Oh, Synth. Commun. 30, 279 (2000).
N. Kamigata, H. Sawada and M. Kobayashi, J. Org. Chem. 48, 3793 (1983).
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Nair, V., Augustine, A., Panicker, S.B. et al. Cerium(IV) ammonium nitrate (CAN)-mediated sulfonylation of styrenes: some interesting observations. Research on Chemical Intermediates 29, 213–226 (2003). https://doi.org/10.1163/156856703321505102
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DOI: https://doi.org/10.1163/156856703321505102