Title: Synthesis and Reactivity of Trifluorodithioacetates Derived from Trifluorothioacetamides
Abstract: Journal für Praktische Chemie/Chemiker-ZeitungVolume 339, Issue 1 p. 697-707 Full Paper Synthesis and Reactivity of Trifluorodithioacetates Derived from Trifluorothioacetamides Frédéric Laduron, Frédéric Laduron Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie OrganiqueSearch for more papers by this authorClaire Nyns, Claire Nyns Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie OrganiqueSearch for more papers by this authorZdenek Janousek, Zdenek Janousek Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie Organique Deceased 17th of July 1996Search for more papers by this authorProf. Heinz G. Viehe, Corresponding Author Prof. Heinz G. Viehe Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie OrganiqueLaboratoire de Chimie Organique, Université catholique de Louvain, Place L. Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium, Fax: 32 10 47 27 88Search for more papers by this author Frédéric Laduron, Frédéric Laduron Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie OrganiqueSearch for more papers by this authorClaire Nyns, Claire Nyns Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie OrganiqueSearch for more papers by this authorZdenek Janousek, Zdenek Janousek Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie Organique Deceased 17th of July 1996Search for more papers by this authorProf. Heinz G. Viehe, Corresponding Author Prof. Heinz G. Viehe Louvain-la-Neuve (Belgium), Université catholique de Louvain, Laboratoire de Chimie OrganiqueLaboratoire de Chimie Organique, Université catholique de Louvain, Place L. Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium, Fax: 32 10 47 27 88Search for more papers by this author First published: 25 October 2004 https://doi.org/10.1002/prac.199733901128Citations: 24 AboutPDF 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 A general synthesis of trifluorodithioacetates is described by thiolysis of trifluorothioamidium salts, derived from trifluorothioacetamides. The reactivity of these CF3 bearing C2 building blocks has been investigated towards nucleophiles and in cycloaddition reactions. Trifluorodithioacetates react with dienes to give thiopyrans and with diazo compounds to give trifluoromethyl vinyl sulphides via thiirane intermediates. With amines, trifluorodithioacetates give rise to trifluorothioacetamides while thiols add by thiophilic attack leading to new trifluoroethane dithioacetal disulphide. Two equivalents of phosphite furnish one equivalent of thiophosphate and one of phosphorylated trifluoroethane. References 1 C. Nyns, PhD. Thesis, Université catholique de Louvain, Prof. H. G. Viehe, 1982 2 M. Rovers-Kevers, L. Vertommen, F. Huys, R. Merényi, Z. Janousek, H. G. Viehe, Angew. Chem., Int. Ed. Engl. 20 (1981) 1023 3 F. Laduron, C. Ates, H. G. Viehe, Tetrahedron Lett. 37 (1996) 5515 4 F. Laduron, PhD Thesis, Université catholique de Louvain, Prof. H. G. Viehe, 1997 5(a) H. C. Brown, R. Pater, J. Org. Chem. 27 (1962) 2858; (b) W. J. Middleton, E. G. Howard, W. H. Sharkey, J. Org. Chem. 30 (1965) 1375 6(a) W. J. Middleton, J. Org. 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