Unusual Trifluoroacetic Anhydride Promoted Fragmentation of a γ,γ,γ-Trifluoro-β-(p-methoxyphenyl-amino) Sulfoxide

Journal of Chemical Research - Part S

Volumn , Issue 11, 1997, Pages 416-417

  Arnone, Alberto ^a   Bravo, Pierfrancesco ^b   Bruché, Luca ^b   Crucianelli, Marcello ^b   Zanda, Matteo ^b   Zappalà, Carmela ^a  

^a CNR   (Italy)

^b POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2542500017     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703814c     Document Type: Article

References (12)

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3. J. E. McCormick and R. S. McElhinney, J. Chem. Soc., Perkin Trans, 1, 1985, 93.
4. (a) P. Bravo, M. Zanda and C. Zappalà, Tetrahedron Lett., 1996, 37, 6005;
5. (b) P. Bravo, A. Farina, V. P. Kukhar, A. L. Markovsky, S. V. Meille, V. A. Soloshonok, A. E. Sorochinsky, F. Viani, M. Zanda and C. Zappalà, J. Org. Chem., 1997, 62, 3424.
6. O. De Lucchi, U. Miotti and G. Modena, Organic Reactions, ed. L. A. Paquette, Wiley, New York, 1991, vol. 40.
7. P. Bravo, G. Cavicchio, M. Crucianelli, A. OL. Markovsky, A. Volonterio and M. Zanda, Synlett., 1996, 887.
8. For recent reports on stable sulfonium salts formed under Pummerer conditions see: (a) M. Amat, S. Hadida, G. Pshenichnyi and J. Bosch, J. Org. Chem., 1997, 62, 3158; (b) M. Amat. M.-L. Bennasar, S. Hadida, B. A. Sufi, E. Zulaica and J. Bosch, Tetrahedron Lett., 1996, 37, 5217.
9. For recent reports on stable sulfonium salts formed under Pummerer conditions see: (a) M. Amat, S. Hadida, G. Pshenichnyi and J. Bosch, J. Org. Chem., 1997, 62, 3158; (b) M. Amat. M.-L. Bennasar, S. Hadida, B. A. Sufi, E. Zulaica and J. Bosch, Tetrahedron Lett., 1996, 37, 5217.
10. We thank Professor J. Bosch for providing us with unpublished experimental data. For unusual Pummerer cyclizations see also: (c) S. G. Pyne and A. R. Hajipour, Tetrahedron, 1994, 50, 13 501.
11. For an overview on the chemistry of sulfonium salts see: (d) The Chemistry of the Sulphonium Group, Parts 1 and 2, ed. C. J. M. Stirling and S. Patai, Wiley, New York, 1981.
12. A. Arnone, P. Bravo, S. Capelli, G. Fronza, S. V. Meille, M. Zanda, G. Cavicchio and M. Crucianelli, J. Org. Chem., 1996, 61, 3375.