Abstract
Cleavage of the lactone ring in 7-phenylbicyclo[3.1.1]heptan-6,7-carbolactone by the action of ammonia and hydrazine and subsequent oxidative cyclization of the resulting hydroxy amide and hydroxy hydrazide gave a cyclic carbamate, 3-oxa-5-azatricyclo[4.4.0.02 , 7]decan-4-one.
Similar content being viewed by others
REFERENCES
Razin, V.V., Zadonskaya, N.Yu., and Makarychev, Yu.A., Zh. Org. Khim., 1990, vol. 26, p. 674; Razin, V.V. and Makarychev, Yu.A., Zh. Org. Khim., 1992, vol. 28, p. 2490; Razin, V.V., Zolotarev, R.N., and Yakovlev, M.E., Russ. J. Org. Chem., 1998, vol. 34, p. 809; Vasin, V.A., Romanova, E.V., Kostryukov, S.G., and Razin, V.V., Mendeleev Commun., 1998, p. 122; Zolotarev, R.N. and Razin, V.V., Russ. J. Org. Chem., 1998, vol. 34, p. 1790.
Razin, V.V. and Zolotarev, R.N., Russ. J. Org. Chem., 2003, vol. 39, p. 1710.
Razin, V.V., Zadonskaya, N.Yu., and Shamurzaev, Kh.T., Zh. Org. Khim., 1991, vol. 27, p. 1253; Razin, V.V. and Makarychev, Yu.A., Russ. J. Org. Chem., 1996, vol. 32, p. 1640.
Christl, M., Gerstner, E., Kemmer, R., Llewellyn, G., and Bentley, T.W., Chem. Ber., 1994, vol. 127, p. 367; Gerstner, E., Kemmer, R., and Christl, M., Chem. Ber., 1994, vol. 127, p. 381.
Simons, S.S., J. Org. Chem., 1973, vol. 38, p. 414.
Shroff, C.C., Stewart, W.S., Uhm, S.J., and Wheeler, J.W., J. Org. Chem., 1971, vol. 36, p. 3356.
Surrey, A.R., Name Reactions in Organic Chemistry, New York: Academic, 1961, 2nd ed. Translated under the title Spravochnik po organicheskim reaktsiyam, Moscow: Goskhimizdat, 1962, pp. 93, 166; Smit, P., Org. React., 1946, vol. 3, pp. 322, 344.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zolotarev, R.N., Razin, V.V. Synthesis of 2-Phenyl-3-oxa-5-azatricyclo[4.4.0.02 , 7]decan-4-one. Russian Journal of Organic Chemistry 39, 1716–1718 (2003). https://doi.org/10.1023/B:RUJO.0000019733.86386.70
Issue Date:
DOI: https://doi.org/10.1023/B:RUJO.0000019733.86386.70