Abstract
Cathodic reduction of α-azidocinnamic ester under aprotic conditions on Hg, Pt, or graphite electrodes can be directed to high yields of N,N-diacylated dehydroaminoacid derivates (f.i. addition of acetic anhydride) or to almost quantitative yields of α-aminocinnamic ester in very pure form by careful addition of H+-donors. The dehydroamino compounds in turn can be further reduced to the corresponding saturated compounds by following H+-addition and changed electrolysis potential. Almost no dimerization occurs.
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Literatur
Knittel D., Monatsh. Chem.115, 523 (1984).
Jeffery E. A., Meisters A., Aust. J. Chem.31, 73, 79 (1978);
Iwasaki T.,Harada K., J. Chem. Soc., Chem. Commun.1974, 338; J. Chem. Soc., Perkin Trans I1977, 1730;
Avrutskaya I. A., Babievskii K. K., Belikov V. M., Zaporohets E. V., Fioshin M. Y., Sov. Elektrochem.9, 1291 (1973).
Srinivasan A., Stephenson R. W., Olsen R. K., J. Org. Chem.42, 2256 (1977);
Ozaki Y., Iwasaki T., Horikawa H., Miyoshi M., Matsumoto K., J. Org. Chem.44, 391 (1979);Hoppe D., Follmann R., Chem. Ber.109, 3062 (1976).
Kagan H. B., Langlois N., Dang T. P., J. Organomet. Chem.90, 353 (1975).
Knittel D., IX. Scand. Meeting on Organic Electrochemistry,1981, 67.
L'abbé G., Angew. Chem.87, 831 (1975).
Lund H.,Degrand Ch., Tetrahedron Lett.1977, 3593.
Hemetsberger H., Hnittel D., Weidmann H., Monatsh. Chem.100, 1599 (1969).
Knittel D., Henning A., Monatsh. Chem.115, 391 (1984).
Shin Ch., Yonezawa Y., Unoki K., Yoshimura J., Bull. Chem. Soc. Japan52, 1657 (1979); Chem. Lett.1976, 1095.
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Knittel, D. Synthese von ungesättigten und gesättigten Aminosäurederivaten durch kathodische Reduktion von Azidozimtsäureester. Monatsh Chem 115, 1335–1343 (1984). https://doi.org/10.1007/BF00798312
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DOI: https://doi.org/10.1007/BF00798312