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Volumn , Issue 19, 2009, Pages 3150-3153

Sulfilimines and sulfoximines by reaction of nitriles with perfluoroalkyl sulfoxides

Author keywords

Fluorine; Nitriles; Sulfilimines; Sulfoximines; Synthetic methods

Indexed keywords


EID: 67650866260     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900410     Document Type: Article
Times cited : (39)

References (54)
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    • We are aware of only one example of nucleophilic attack on such species, described by Yagupolskii and co-workers concerning the specific reaction of trifluoromethanesulfonamine with trifluoromethyl phenyl sulfoxide: N. V. Kondratenko, V. I. Popov, G. N. Timofeeva, N. V. Ignat'ev, L. M. Yagupolskii, Zh. Org. KMm. 1984, 20, 2599-2604;
    • a) We are aware of only one example of nucleophilic attack on such species, described by Yagupolskii and co-workers concerning the specific reaction of trifluoromethanesulfonamine with trifluoromethyl phenyl sulfoxide: N. V. Kondratenko, V. I. Popov, G. N. Timofeeva, N. V. Ignat'ev, L. M. Yagupolskii, Zh. Org. KMm. 1984, 20, 2599-2604;
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    • For preparation of highly fluorinated sulfilimines see: a
    • For preparation of highly fluorinated sulfilimines see: a) L. C. Duncan, Inorg. Chem. 1970, 9, 987-989;
    • (1970) Inorg. Chem , vol.9 , pp. 987-989
    • Duncan, L.C.1
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    • and references cited herein
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    • Collet, F.1    Dodd, R.H.2    Dauban, P.3
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    • 19F NMR spectroscopy. See the corresponding spectra in Supporting Information.
    • 19F NMR spectroscopy. See the corresponding spectra in Supporting Information.
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    • X-ray structure of sulfoximine 23 has also been obtained. The crystal data for 5, 10 and 23 are detailed in the Supporting Information. CCDC-724941 (5), -724942 (10) and -724943 (23) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
    • X-ray structure of sulfoximine 23 has also been obtained. The crystal data for 5, 10 and 23 are detailed in the Supporting Information. CCDC-724941 (5), -724942 (10) and -724943 (23) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • Safety remarks When this reaction is conducted on a large scale (1.0 g of sulfoxide or more), the addition of sodium azide can set the reaction mixture on fire.
    • Safety remarks When this reaction is conducted on a large scale (1.0 g of sulfoxide or more), the addition of sodium azide can set the reaction mixture on fire.
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    • [18.19]), probably due to secondary oxidation process on benzylic position.
    • [18.19]), probably due to secondary oxidation process on benzylic position.
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    • The sulfoxides have been prepared from the corresponding thiol by our previously described methods: a A. Anselmi, J.C. Blazejewski, M. Tordeux, C. Wakselman, J. Fluorine Chem. 2000, 105, 41-44;
    • The sulfoxides have been prepared from the corresponding thiol by our previously described methods: a) A. Anselmi, J.C. Blazejewski, M. Tordeux, C. Wakselman, J. Fluorine Chem. 2000, 105, 41-44;
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    • E. Magnier, M. Tordeux, R. Goumont, K. Magder, C Wakselman, J. Fluorine Chem. 2003, 124, 55-59. See also the Supporting Information.
    • b) E. Magnier, M. Tordeux, R. Goumont, K. Magder, C Wakselman, J. Fluorine Chem. 2003, 124, 55-59. See also the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.