Abstract
Hex-5-ynoic acid, a multipurpose synthon, was synthesized in three steps starting from cyclohexanone by bromination-dehydrobromination of the intermediate hex-5-enoic acid.
Similar content being viewed by others
References
J. M. Osbond, P. J. Philpott, and J. C. Wickens,J. Chem. Soc., 1961, 2779; (b) E. J. Corey, J. Kang, B. C. Laguzza, and R. L. Jones,Tetrahedron Lett., 1983,24, 4913; (c) E. J. Corey and W.-G. Su.Tetrahedron Lett., 1984,25, 5115; (d) G. Heslinga, R. van der Linde H. J. J. Pabon, D. A. Dorp, P.-Y. Kwok, F. W. Muellner, C.-K. Chen, and J. Fried,J. Am. Chem. Soc., 1987,109, 3684; (e) L. L. Vasiljeva, T. A. Manukina, P. M. Demin, and K. K. Pivnitsky,Tetrahedron, 1993,49, 4099; (f) P. M. Demin, T. A. Manukina, C. R. Pace-Asciak, and K. K. Pivnitsky,Mendeleev Commun., 1996, 130.
H. Gerlach and P. Kunzler,Helv. Chim. Acta, 1980,63, 2312.
G. Eglington and M. C. Whiting,J. Chem. Soc., 1953, 3052; (b) G. I. Myagkova, P. M. Demin, Yu. Yu. Belosludtsev, D. A. Zabolotskii, and R. P. Evstigneeva,Bioorgan. Khim., 1987,13, 415 [Sov. Bioorg. Chem., 1987,13 (Engl. Transl.)].
G. Just, C. Luthe, H. Oh, and J. Montgomery,Synth. Commun., 1979,9, 613; (b) G. A. Krafft and J. A. Katzenellebogen,J. Am. Chem. Soc., 1981,103, 5459.
Fluka Catalog, Chemika, BioChemika, Analytika, 1997/98, 799, Cat. No. 53108, 331.30 DM/5 g.
A. E. De La Mare, J. K. Kochi, and F. F. Rust,J. Am. Chem. Soc., 1963,85, 1437; (b) E. K. Starostin, A. V. Aleksandrov, and G. I. Nikishin,Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 2260 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35, 2064 (Engl. Transl.)].
A. Seher,Lieb. Ann., 1954,589, 222.
E. R. H. Jones, M. C. Whitman, and M. C. Whiting,J. Chem. Soc., 1954, 3201.
Y. Kimura and S. L. Regen,J. Org. Chem., 1982,47, 2493.
L. Brandsma, inPreparative Acetylenic Chemistry, 2nd ed., Elsevier, Amsterdam-Oxford-New York-Tokyo, 1988, 173.
R. W. Carling, Ph. D. Thesis, University of Cambridge (U.K.), 1986, 150.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 78–81, January, 2000.
Rights and permissions
About this article
Cite this article
Starostin, E.K., Lapitskaya, M.A., Ignatenko, A.V. et al. Practical synthesis of hex-5-ynoic acid from cyclohexanone. Russ Chem Bull 49, 81–84 (2000). https://doi.org/10.1007/BF02499070
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02499070