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Ortho-Formylierung von Anilinen durch Umlagerung von Bis(methylthio)methan-S-(N-aryl)imiden

Ortho-formylation of anilines by rearrangement of bis(methylthio)methane-S-(N-aryl)imides

  • Organische Chemie And Biochemie
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Abstract

By reaction of anilines with dithioacetals of formaldehyde [in particular, with bis(methylthio)methane] andtert. butylhypochlorite the corresponding intermediate mono-sulfimides are formed which rearrange easily—after addition of triethylamine—to yield dithioacetals5 ofo-amino benzaldehydes.

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Literatur

  1. Teil der Dissertation vonJäger E., „Beiträge zur Chemie hochreaktiver Sulfimide“, Universität Wien, 1980.

  2. Teil der Dissertation vonSetzer A., „Über einige Aspekte zur oxidativen Iminierung α-substituierter Sulfide“, Universität Wien, 1982.

  3. Smith L. I., Opie J. W., Organic Synthesis, Coll. Vol. III, 56 (1955).

    Google Scholar 

  4. Brown J. J.,Newbold G. T., J. Chem. Soc.1952, 4878.

  5. Sugasawa T.,Hamana H.,Toyoda T.,Adachi M., Synthesis1979, 99.

  6. Gassman P. G., Drewes H. R., J. Amer. Chem. Soc.96, 3002 (1974).

    Google Scholar 

  7. Claus P. K.,Rieder W.,Hofbauer P., 6th International Symposium on Organic Sulphur Chemistry, Bangor (Wales), Abstracts Book D 26 (1974).

  8. Claus P. K., Rieder W., Hofbauer P., Vilsmaier E., Tetrahedron31, 505 (1975).

    Google Scholar 

  9. Seidl F., Chem. Ber.59, 1894 (1926).

    Google Scholar 

  10. McGeachin S. G., Can. J. Chem.44, 2323 (1966).

    Google Scholar 

  11. Bailer J., Claus P. K., Vierhapper F. W., Tetrahedron36, 901 (1980).

    Google Scholar 

  12. Claus P., Rieder W., Monatsh. Chem.103, 1163 (1972).

    Google Scholar 

  13. Claus P. K., Rieder W., Vierhapper F. W., Bailer J., Tetrahedron35, 1373 (1979).

    Google Scholar 

  14. Claus P. K.,Silbernagel W.,Franek W.,Rieder W., Monatsh. Chem.116 (1985), im Druck.

  15. Gourcy J., Martigny P., Simonet J., Jeminet G., Tetrahedron37, 1495 (1981).

    Google Scholar 

  16. Teeter H. M., Bell E. W., Organic Synthesis, Coll. Vol. IV, 125 (1963).

    Google Scholar 

  17. Braun M., Seebach D., Chem. Ber.109, 669 (1976).

    Google Scholar 

  18. Heriott A. W., Synthesis1975, 447.

  19. Brookes R. F., Cranham J. E., Cummings W. A., Greenwood D., Jackson B. S., Stevenson H. A., J. Sci. Food Agr.8, 31 (1957); Chem. Abstr.51, 9628 h (1957).

    Google Scholar 

  20. Ogura K., Suzuki M., Tsuchihashi G., Bull. Chem. Soc. Japan53, 1414 (1980).

    Google Scholar 

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Herrn emer. o. Univ. Prof. Dr.O. Hromatka zum 80. Geburtstag gewidmet.

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Claus, P.K., Jäger, E. & Setzer, A. Ortho-Formylierung von Anilinen durch Umlagerung von Bis(methylthio)methan-S-(N-aryl)imiden. Monatsh Chem 116, 1017–1026 (1985). https://doi.org/10.1007/BF00809194

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  • DOI: https://doi.org/10.1007/BF00809194

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