Abstract
Addition of phthalimidonitrene to 1-(1-octynyl)- and 1-(phenylethynyl)-cyclopentene takes place exclusively at the double bond to give the bicyclic N-phthalimidoaziridines in ∼40% yield.
Similar content being viewed by others
Literature Cited
B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, The Chemistry of Organic Hydrazine Compounds [in Russian], Khimiya, Leningrad (1979), p. 134.
V. N. Belov, Current Topics in Organic Chemistry (K. A. Ogloblin, editor) [in Russian], Leningrad State University Press (Izd. LGU) (1986), No. 8, p. 4.
D. J. Anderson, T. L. Gilchrist, G. E. Gymer, and C. W. Rees, J. Chem. Soc., Perkin 1, No. 6, 550 (1973).
S. Szántay and L. Novak, Synthesis of Prostaglandins, Akadémiai Kiadó (1974), p. 166.
M. A. Kuznetsov and V. N. Belov, Zh. Org. Khim., 20, 1768 (1984).
G. V. Shustov, S. N. Denisenko, I. I. Chervin, N. L. Asfandiarov, and R. G. Kostyanovsky, Tetrahedron, 41, 5719 (1985).
C. N. R. Rao, P. K. Basu, and M. S. Hedge, Appl. Spectrosc. Rev., 15, 1 (1979).
W. K. Franke and H. Neunhoeffer, Methoden der Organischen Chemie (E. Müller, ed.) Georg Thieme Verlag, Stuttgart (1972), Bd. B/1d., S. 692.
N. S. Zefirov, I. V. Kazimirchuk, and K. A. Lukin, Cycloaddition of Carbenes to Olefins [in Russian], Nauka, Mosow (1985), p. 134.
K. Eichinger, Monatsh. Chem., 106, 1213 (1975).
K. Sonogashira, Y. Tohda, and N. Hagihara, Tetr. Lett., No. 50, 4467 (1975).
H. D. Drew and H. H. Hatt, J. Chem. Soc., No. 1, 16 (1937).
L. Fieser and M. Fieser, Reagents for Organic Synthesis [Russian translation], Mir, Moscow (1970), Vol. 3, p. 208.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1055–1057, August, 1988.
Rights and permissions
About this article
Cite this article
Belov, V.N., Denisov, V.R. & Kuznetsov, M.A. Reactions of phthalimidonitrene with conjugated enamines. Synthesis of 1-amino-2-ethynylaziridine. Chem Heterocycl Compd 24, 868–870 (1988). https://doi.org/10.1007/BF00479338
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00479338