Reactivity of Sulfur-Centered Radicals with Indolinonic and Quinolinic Aminoxyls
1999; Wiley; Volume: 1999; Issue: 9 Linguagem: Inglês
10.1002/(sici)1099-0690(199909)1999
ISSN1434-193X
AutoresElisabetta Damiani, Patricia Carloni, Marco Iacussi, Pierluigi Stipa, Lucedio Greci,
Tópico(s)Sulfur-Based Synthesis Techniques
ResumoEuropean Journal of Organic ChemistryVolume 1999, Issue 9 p. 2405-2412 Full Paper Reactivity of Sulfur-Centered Radicals with Indolinonic and Quinolinic Aminoxyls Elisabetta Damiani, Elisabetta Damiani Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorPatricia Carloni, Patricia Carloni Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorMarco Iacussi, Marco Iacussi Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorPierluigi Stipa, Pierluigi Stipa Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorLucedio Greci, Lucedio Greci [email protected] Search for more papers by this author Elisabetta Damiani, Elisabetta Damiani Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorPatricia Carloni, Patricia Carloni Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorMarco Iacussi, Marco Iacussi Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorPierluigi Stipa, Pierluigi Stipa Dipartimento di Scienze dei Materiali e della Terra, Università, Via Brecce Bianche, I-60131 Ancona, Italy Fax: (internat.) +39-071/2204714Search for more papers by this authorLucedio Greci, Lucedio Greci [email protected] Search for more papers by this author First published: 12 August 1999 https://doi.org/10.1002/(SICI)1099-0690(199909)1999:9 3.0.CO;2-RCitations: 16AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Indolinonic, phenylimino-indolinonic and quinolinic aromatic aminoxyls readily react with sulfur-centered radicals, generated upon reaction with p-methylthiophenol at room temperature. The main product is the deoxygenated derivative i.e. the corresponding amine. The other compounds, obtained in low yields, are N-substituted amines and amines substituted in a conjugated position with respect to the amino group by arylthiyl, arylsulphinyl, arylsulphonyl and arylsulphonyloxy radicals. The formation of the products are explained by the initial attack of the thiophenol radical onto the NO· function to give an unstable adduct which decomposes to aminyl and arylsulphinyl radicals. From here the reaction can take two different routes to give the products obtained. References 1[1a] J. F. W. Keana, in Spin Labeling II: Theory and Applications (Ed.: J. L. Berliner), Academic Press Inc., New York, 1979, chapter 3, p. 115–172. 10.1016/B978-0-12-092352-6.50009-2 Google Scholar[1b] – L. H. Piette, J. Carleton Hsia in Spin Labeling II: Theory and Applications (Ed.: J. L. Berliner), Academic Press Inc., New York, 1979, chapter 6, p. 247–290. 10.1016/B978-0-12-092352-6.50012-2 Google Scholar 2 H. M. Swartz in Advances in Magnetic Resonance Imaging (Ed.: E. Feig) Ablex Publishing Co., Norwood, NJ, 1989, p. 49. Google Scholar 3 N. Kocherginsky, H. M. Swartz in Nitroxide Spin Labels: Reactions in Biology and Chemistry (Eds.: N. Kocherginsky, H. M. Swartz) CRC Press, Boca Raton, New York, 1995, chapter 3, p. 46–48. Google Scholar 4[4a] S. Al-Malaika in Comprehensive Polymer Science (Eds.: C. Booth, C. Price) Pergamon Press, Oxford, 1989, vol. 2, p. 539. 10.1016/B978-0-08-096701-1.00199-3 Google Scholar[4b] – F. Gugumus, Polym. Deg. Stab., 1993, 40, 167. 10.1016/0141-3910(93)90208-Z CASWeb of Science®Google Scholar 5 P. Carloni, E. Damiani, M. Iacussi, L. Greci, P. Stipa, P. Cauzi, C. Rizzoli, P. Sgarabotto, Tetrahedron, 1995, 51, 12445–12452. 10.1016/0040-4020(95)00800-N CASWeb of Science®Google Scholar 6 L. Greci, E. Damiani, P. Carloni, P. Stipa in Free Radicals in Biology and Environment (Ed.: F. Minisci) Kluwer Academic Publishers, Dordrecht, Boston, London, 1997, p. 223–232. 10.1007/978-94-017-1607-9_16 Web of Science®Google Scholar 7 C. Berti, L. Greci, L. Marchetti, J. Chem. Soc. Perkin Trans. 2, 1979, 233–236. Google Scholar 8 C. Berti, M. Colonna, L. Greci, L. Marchetti, Tetrahedron, 1975, 31, 1745–1753. 10.1016/0040-4020(75)85098-8 CASWeb of Science®Google Scholar 9 A. K. Bhattacharya, A. G. Hortmann, J. Org. Chem., 1978, 43, 2728–2730. 10.1021/jo00407a049 CASWeb of Science®Google Scholar 10 C. Berti, L. Greci, L. Marchetti, J. Chem. Soc. Perkin Trans. 2, 1977, 1032–1035. Google Scholar 11 P. Carloni, E. Damiani, L. Greci, P. Stipa, C. Rizzoli, P. Sgarabotto, F. Ugozzoli, Tetrahedron, 1993, 49, 5099–5108. 10.1016/S0040-4020(01)81875-5 CASWeb of Science®Google Scholar 12[12a] L. Greci, Tetrahedron, 1983, 39, 677–681. 10.1016/S0040-4020(01)91844-7 CASWeb of Science®Google Scholar[12b] – C. Berti, L. Greci, J. Org. Chem., 1981, 46, 3060–3063. 10.1021/jo00328a014 CASWeb of Science®Google Scholar[12c] – P. Carloni, E. Damiani, L. Greci, P. Stipa, Acta Chem. Scand., 1998, 52, 137–140. 10.3891/acta.chem.scand.52-0137 CASWeb of Science®Google Scholar[12d] – C. Berti, M. Colonna, L. Greci, L. Marchetti, Tetrahedron, 1977, 33, 3149–3154; 10.1016/0040-4020(77)80464-X CASWeb of Science®Google Scholar C. Berti, M. Colonna, L. Greci, L. Marchetti, Tetrahedron, 1977, 33, 2321–2327. 10.1016/0040-4020(77)80022-7 CASWeb of Science®Google Scholar[12e] – L. Greci, J. Chem. Res. (S), 1979, 204–205. Google Scholar[12f] – L. Cardellini, P. Carloni, E. Damiani, L. Greci, P. Stipa, C. Rizzoli, P. Sgarabotto, J. Chem. Soc. Perkin Trans. 2, 1994, 769–773. 10.1039/p29940000769 Web of Science®Google Scholar 13 H. Friebolin in Basic One- and Two- Dimensional NMR Spectroscopy (Ed.: E. E. Wille) Weinheim: VCH, 1991, chapter 3, p. 84. Google Scholar 14 P. Carloni, L. Cardellini, L. Greci, P. Stipa, A. Faucitano, Gazz. Chim. Ital., 1989, 119, 621–625. Web of Science®Google Scholar 15 L. Greci, Tetrahedron, 1982, 38, 2435–2439. 10.1016/0040-4020(82)87024-5 CASWeb of Science®Google Scholar 16 A. Alberti, L. Greci, P. Stipa, P. Sgarabotto, F. Ugozzoli, Tetrahedron, 1987, 43, 3031–3040. 10.1016/S0040-4020(01)86843-5 CASWeb of Science®Google Scholar 17[17a] P. Carloni, L. Greci, P. Stipa, L. Eberson, J. Org. Chem., 1991, 56, 4733–4737. 10.1021/jo00015a029 CASWeb of Science®Google Scholar[17b] – P. Stipa, L. Greci, P. Carloni, E. Damiani, Polym. Degrad. Stab., 1997, 55, 323–327. 10.1016/S0141-3910(96)00168-1 CASWeb of Science®Google Scholar 18 R. M. Topping, N. Khararsch, J. Org. Chem., 1962, 27, 4353–4356. 10.1021/jo01059a052 CASWeb of Science®Google Scholar 19 S. Oae, K. Ikawa, Bull. Chem. Soc. Japan, 1965, 38, 58–62. 10.1246/bcsj.38.58 CASWeb of Science®Google Scholar 20[20a] C. Brown, R. F. Hudson, K. A. F. Record, J. Chem. Soc. Perkin Trans. 2, 1977, 822–828. Google Scholar[20b] – W. J. Bouma, J. B. F. N. Engberts, J. Org. Chem., 1976, 41, 143–145. 10.1021/jo00863a033 CASWeb of Science®Google Scholar[20c] – I. P. Bleeker, J. B. F. N. Engberts, J. Org. Chem., 1981, 46, 1012–1014. 10.1021/jo00318a033 CASWeb of Science®Google Scholar 21 P. G. Gassman, G. A. Campbell, J. Chem. Soc. Chem. Comm., 1971, 1437–1438. Google Scholar 22[22a] C. Chatgiliagolu, B. C. Gilbert, B. Gill, M. D. Sexton, J. Chem. Soc. Perkin Trans. 2, 1980, 1141–1150. Google Scholar[22b] – C. Chatgiliagolu in The chemistry of sulphones and sulphoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling), John Wiley&Sons Ltd., London, 1988, chapter 24, p. 1081–1087. 10.1002/0470034386.ch24 Google Scholar 23[23a] J. E. Bennet, G. Brunton, B. C. Gilbert, P. E. Whittall, J. Chem. Soc. Perkin Trans. 2, 1988, 1359–1364. Google Scholar[23b] – C. M. M. da Silva Correa, W. A. Waters, J. Chem. Soc. (C), 1968, 1874–1879. Google Scholar[23c] – C. Chatgiliagolu in The chemistry of sulphones and sulphoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling), John Wiley&Sons Ltd., London, 1988, chapter 25, p. 1089–1113. 10.1002/0470034386.ch25 Google Scholar 24[24a] K. Nishikida, F. Williams, J. Am. Chem. Soc., 1974, 96, 4781–4784. 10.1021/ja00822a010 CASWeb of Science®Google Scholar[24b] – M. McMillan, W. A. Waters, J. Chem. Soc. (B), 1966, 422. Google Scholar 25 HyperChem, release 4.5, available from Hypercube. Waterloo: Canada. Google Scholar 26 C. Berti, M. Colonna, L. Greci, L. Marchetti, Tetrahedron, 1976, 32, 2147–2151. 10.1016/0040-4020(76)85126-5 CASWeb of Science®Google Scholar 27 M. J. Dewar, E. G. Zoebisck, E. F. Healey, J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902–3909. 10.1021/ja00299a024 CASWeb of Science®Google Scholar 28 G. Chang, W. C. Guida, W. C. Still, J. Am. Chem. Soc., 1989, 111, 4379–4386. 10.1021/ja00194a035 CASWeb of Science®Google Scholar Citing Literature Volume1999, Issue9September 1999Pages 2405-2412 ReferencesRelatedInformation
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