Summary
A series of alkyl- and arylsulfenanilides has been prepared by thermal cycloelimination of acrylonitrile or methyl acrylate from N-aryl sulfimides derived from 3-alkylthio-propionitriles or methyl 3-alkylthio-propanoates. Compared to reactions in earlier studies [1] cycloelimination proceeds much faster at very mild conditions, thus allowing a one-pot synthesis of sulfenanilides from corresponding 3-alkyl-thio-propionitriles or 3-alkylthio-propanoates.
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Teil 1: Claus P. K, Silbernagel W., Franek W., Rieder W. (1985) Monatsh. Chem.116: 841; Teil der Dissertation von W. Franek “Sulfenamide aus Sulfimiden”, Universität Wien 1988; vorgetragen bei den 7. Österr. Chemietagen, Wien, 3. −6. 11. 1987, und bei dem 13th International Symposium on the Organic Chemistry of Sulfur, Odense 1988 (Abstr. of Papers, PA4, S. 90)
Davis F. A. (1979) Org. Prep. Proced. Intern.11: 13
Craine L., Raban M. (1989) Chem. Rev.89: 689
Trost B. M., Salzmann T. N., Hiroi K. (1976) J. Am. Chem. Soc.98: 4887
Jones D. N., Hill D. R., Lewton D. A., Sheppard C. (1977) J. Chem. Soc., Perkin Trans. I1977: 1574
Oae S., Tsujihara T., Furukawa N. (1970) Tetrahedron Letters1970: 2663
Oae S., Furukawa N. (1977) Tetrahedron33: 2359
Katritzky A. R., Takahashi I., Marson C. M. (1986) J. Org. Chem.51: 4914
Yamamoto T., Kakimoto M., Maejima T., Okawara M. (1983) Bull. Chem. Soc. Jpn.56: 1249
Claus P. K., Rieder W., Hofbauer P., Vislmaier E. (1975) Tetrahedron31: 505
Manuskript in Vorbereitung
Taylor E. C., Fletcher S. R., Sabb A. L. (1984) Synth. Commun.14: 921
Hurd C. D., Gershbein L. L. (1947) J. Am. Chem. Soc.69: 2328
Pretsch E., Clerc T., Seibl J., Simon W. (1986) Tabellen zur Strukturaufklärung organischer Verbindungen. Springer, Berlin Heidelberg New York, S. C120
Ewing D. F. (1979) Org. Magn. Res.12: 499
Teeter H. M., Bell E. W. (1963) Org. Syntheses, Coll. Vol.4: 125
Doering W. v. E., Schreiber K. C. (1955) J. Am. Chem. Soc.77: 514
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Franek, W., Claus, P.K. Alkyl- und Arylsulfensäureanilide durch Cycloeliminierung von Alkenen aus Sulfimiden, 2. Thermolyse von 3-Alkylthiopropannitril-bzw. 3-Alkylthiopropansäuremethylester-S-(N-aryl)-imiden. Monatsh Chem 121, 385–392 (1990). https://doi.org/10.1007/BF00809455
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DOI: https://doi.org/10.1007/BF00809455