Journals / Turkish Journal of Chemistry / 2006 / Cilt: 30 - Sayı: 2

Synthesis of n-Alkylnaphthalenes via Semicarbazones

Pages
139–144
Publication Date
2006-02-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

This study offers an excellent preparative method for the synthesis of 1-n-alkylnaphthalenes from semicarbazones, via a 3-step procedure.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:A number of 1-n-alkylnaphthalenes were prepared via the respective semicarbazones.
📊
Key Findings & Data:The semicarbazones were reduced by modified Wolff-Kishner reductions to give 1-n-alkylnaphthalenes in excellent yields as manageable yellow or orange viscous oils.
💡
Conclusion & Impact:This study offers an excellent preparative method for the synthesis of 1-n-alkylnaphthalenes from semicarbazones, via a 3-step procedure.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Alkylnaphthalenes · Semicarbazones · Wolff-Kishner reductions

Abstract

A number of 1-n-alkylnaphthalenes were prepared via the respective semicarbazones. The semicarbazones were reduced by modified Wolff-Kishner reductions to give 1-n-alkylnaphthalenes in excellent yields as manageable yellow or orange viscous oils. The semicarbazones were prepared from ketones, which are the addition products of Grignard reagents to nitriles. This study offers an excellent preparative method for the synthesis of 1-n-alkylnaphthalenes from semicarbazones, via a 3-step procedure.

Özet

A number of 1-n-alkylnaphthalenes were prepared via the respective semicarbazones. The semicarbazones were reduced by modified Wolff-Kishner reductions to give 1-n-alkylnaphthalenes in excellent yields as manageable yellow or orange viscous oils. The semicarbazones were prepared from ketones, which are the addition products of Grignard reagents to nitriles. This study offers an excellent preparative method for the synthesis of 1-n-alkylnaphthalenes from semicarbazones, via a 3-step procedure.

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Cite This Article

ZENGİN, G., HUFFMAN, J. W. (2006). Synthesis of n-Alkylnaphthalenes via Semicarbazones. Turkish Journal of Chemistry, Cilt: 30 - Sayı: 2, 139–144. https://ajindex.com/articles/218013

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References (19)

  1. W.G. Dauben, Org. React. 19, 422 (1972).
  2. R.G. Jones and H. Gilman, Org. React. 6, 339-66 (1951). B.J. Wakefield “Organolithium Methods in Organic Synthesis”, Academic Press, 1990.
  3. R.E. Merrill and E. Negishi, J. Org. Chem. 39, 3452-53 (1974).
  4. I. Kondolff, H. Doucet and M. Santelli, Tetrahedron, 60 (17), 3813-18 (2004).
  5. D. Laurenti, M. Feuerstein, G. Pepe, H. Doucet and M. Santelli, J. Org Chem. 6 (5), 1633-7 (2001).
  6. R.L. Shriner and T.A. Turner, J. Am. Chem. Soc. 52, 1267-69 (1930). B.J. Wakefield, “Organomagnesium Methods in Organic Synthesis” Academic Press, 1995. G.A. Silverman and P.E. Rakita, “Handbook of Grignard Reagents”, Marcel Dekker, 1996.
  7. S.H. Morrell, G.B. Pickering and J.C. Smith. J. Institute of Petroleum, 34, 677-91 (1948). P. Cagniant and D. Cagniant Bull. Soc. Chim. Fr. 1448-58 (1958).
  8. B. Bannister and B.B. Elsner, J. Chem. Soc. 1055-60 (1951). International Agency for Research on Cancer, “Cadmium and Cadmium Compounds-IARC Mono- graphs on the Evaluation of Carcinogenic Risks to Humans” Supplement 7, 140-142 (1987).
  9. R.L. Shriner, R.C. Fuson and D.Y. Curtin,“Systematic Identification of Organic Compounds”, John Wiley and Sons Inc., New York, 1956.
  10. R.O. Hutchins, M. Kacher and L. Rua, J. Org. Chem. 40, 923-26 (1975).
  11. F. Baerts, Bull. Soc. Chim. Belg. 31, 184 (1922).
  12. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett. 16, 4467-70 (1975).
  13. G. Zengin, Ph.D. Dissertation, Clemson University, South Carolina, 2003.
  14. J.W. Huffman, G. Zengin, M.-J. Wu, J. Lu, G. Hynd, K Bushell, A L. S. Thompson, S. Bushell, C. Tartal, D.P. Hurst, P.H. Reggio, D.E. Selley, M.P. Cassidy, J.L. Wiley and B.R. Martin, Bioorg. Med. Chem. 13, 112 (2005).
  15. L. Lin and L. Paquette, Synth. Comm. 24, 2503-06 (1994). Y.S. Zal’kind and S. Zonis, J. Gen. Ch. U.S.S.R. 6, 988-98 (1936).
  16. A.D. Petrov, O.M. Nefedov and I.I. Bufatin, Zh. Obshch. Khim. 29, 3901-08, engl. Ausg. S. 3860-67 (1959).
  17. E. Clemmensen, Ber. Dtsch. Chem. Ges. 46, 1837 (1913).
  18. G. Harris, J.R.A. Pollock, and R. Stevens (eds), “Dictionary of Organic Compounds”, Oxford University Press,
  19. New York, NY, 1965.