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Use of phenylselenyl chloride in the preparation of methyl 11-phenylseleno-10-acetamido- and ethyl phenylselenoethoxy fatty alkanoates

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Journal of the American Oil Chemists' Society

Abstract

Reaction of methyl 10-undecenoate (I) with phenylselenyl chloride in acetonitrile furnished methyl 11-phenylseleno-10-acetamido-undecanoate (II) as a major product, and a similar reaction of I with phenylselenyl chloride in absolute ethanol gave ethyl 11-phenylseleno-10-ethoxy-undecanoate (III) as a sole product. A similar reaction of methyl octadec-cis-9-enoate (IV; oleate) with phenylselenyl chloride in absolute ethanol was conducted and resulted in the formation of ethyl 10(9)-phenylseleno-9(10)-ethoxy-octadecanoate (V).

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References

  1. Demarcus, M., S.N. Filigheddu, A. Mann, and M. Taddei, Stereoselective Addition of Phenylselenyl Chloride to Methoxy Alkenes Derived from N-Protected Chiral α-Amino Acids, Tetrahedron Lett. 40:4417–4420 (1999).

    Article  CAS  Google Scholar 

  2. El-Laghdach, A., M.I. Matheu, and S. Castillon, Synthesis of 2′-Deoxy-pyranosyl Nucleosides from Glycals Through Consecutive Addition of Phenylselenenyl Chloride and Glycosylation. A Study of Factors Controlling the Stereoselectivity, Tetrahedron 50:12219–12234 (1994).

    Article  CAS  Google Scholar 

  3. Cooper, M.A., C.L. Francis, J.W. Holman, B. Kasum, T. Taverner, E.R.T. Tiekink, and A.D. Ward, The Reactions of N-Substituted 2-(Dimethylallyl) Aniline Compounds with Phenylselanyl Halides, Aust. J. Chem. 53:123–129 (2000).

    Article  CAS  Google Scholar 

  4. McCarthy, J.R., D.P. Matthews, and C.L. Barney, A New Synthesis of 2-Fluoro 1-Olefins, Tetrahedron Lett. 31:973–976 (1990).

    Article  CAS  Google Scholar 

  5. Nicoalaou, K.C., S.P. Seitz, W.J. Sipio, and J.F. Blount, Phenylseleno- and Phenylsulfenolactonizations. Two Highly Efficient and Synthetically Useful Cyclization Procedures, J. Am. Chem. Soc. 101:3884–3893 (1979).

    Article  Google Scholar 

  6. Clive, D.L.J., V. Farina, A. Singh, C.K. Wong, W.A. Kiel, and S.M. Menchen, Cyclofunctionalization of Olefinic Urethanes Using Benzeneselenenyl Chloride in the Presence of Silica Gel. A General Route to Nitrogen Heterocycles, J. Org. Chem. 45: 2120–2126 (1980).

    Article  CAS  Google Scholar 

  7. De Kimpe, N., and M. Boelens, Organoselenium Induced Cyclisation of γ, δ-Alkenimines to Nitrogen Heterocycles, J. Chem. Soc., Chem. Comm.:916–918 (1993).

  8. Engman, L., Functional Group Manipulation via Organoselenium-and Halogen-Induced Cyclofunctionalization/Hydrolysis of Allylic Benzimidates, Tertiary Benzamides and Benzamidines. Regioflexible Synthesis of Amino Alcohol Derivatives, J. Org. Chem. 58:2394–2401 (1993).

    Article  CAS  Google Scholar 

  9. Holmes, A.B., A. Nadin, P.J. O’Hanlon, and N.D. Pearson, Synthesis of Optically Active α-Phenylselenyl Carbonyl Derivatives, Tetrahedron Assym. 3:1289–1302 (1992).

    Article  CAS  Google Scholar 

  10. Hart, D.J., S. Patterson, and A. Zakarian, Substituent Effects on Stereochemical Course of Electrophile-Initiated Tetrahydropyran Forming Reactions: A Possible Stereoelectronic Effect, Heterocycles 52:1025–1028 (2000).

    Article  CAS  Google Scholar 

  11. Toshimitsu, A., T. Aoai, S. Uemura, and M. Okano, Simple Procedure for the Aminoselenation of Olefins, J. Chem. Soc. Chem. Comm.:1041–1042 (1980).

  12. Takahashi, T., H. Nagashima, and J. Tsuji, Preparation of 1-Phenylseleno 2-Alkanones from Terminal Olefins and Their Application to Organic Synthesis, Tetrahedron Lett.:799–802 (1978).

  13. Siddiqui, M.M., F. Ahmad, and S.M. Osman, The Synthesis of Organoselenium Compounds from Two Methyl Undecynoates, J. Chem. Res. (S):362 (1985); J. Chem. Res. (M); 3739–3747 (1985).

  14. Reich, H.J., I.L. Reich, and J.M. Renga, Organoselenium Chemistry. α-Phenylseleno Carbonyl Compounds as Precursors for α,β-Unsaturated Ketones and Esters, J. Am. Chem. Soc. 95: 5813–5815 (1973).

    Article  CAS  Google Scholar 

  15. Sharpless, K.B., R.F. Lauer, and A.Y. Teranishi, Electrophilic and Nucleophilic Organoselenium Reagents. New Routes to α,β-Unsaturated Carbonyl Compounds, Ibid. 95:6137–6139 (1973).

    Article  CAS  Google Scholar 

  16. Mugesh, G., W.W. du Mont, and H. Sies, Chemistry of Biologically Important Synthetic Organoselenium Compounds, Chem. Rev. 101:2125–2179 (2001).

    Article  CAS  Google Scholar 

  17. Agarwal, R., A. Rauf, M. Khan, J. Mustafa, and M. Ahmad, Organoselenium Mediated Cyclization of Hydroxy Olefinic Fatty Acids and m-CPBA Oxidation of Selenium Containing 1,4-Epoxy Acids, J. Am. Oil Chem. Soc. 67:932–936 (1990).

    CAS  Google Scholar 

  18. Francis, M.D., C. Jones, P.C. Junk, and J.L. Roberts, 1,2-Addition of Phenylselenyl Halides to Phosphoalkynes, Phosphorus, Sulfur, Silicon Relat. Elem. 130:23–24 (1997).

    CAS  Google Scholar 

  19. Christie, W.W., Lipid Analysis, Pergamon Press, Oxford, 1973, pp. 88–90.

    Google Scholar 

  20. Raucher, S., The Synthesis of Vinyl Bromides and Allyl Bromides from Monosubstituted Alkenes, Tetrahedron Lett.: 3909–3912 (1977).

  21. Raucher, S., Regioselective Synthesis of Vinyl Phenylselenides, J. Org. Chem. 42:2950–2951 (1977).

    Article  CAS  Google Scholar 

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Correspondence to Abdul Rauf.

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Ahmad, S., Rauf, A. Use of phenylselenyl chloride in the preparation of methyl 11-phenylseleno-10-acetamido- and ethyl phenylselenoethoxy fatty alkanoates. J Amer Oil Chem Soc 80, 1049–1055 (2003). https://doi.org/10.1007/s11746-003-0819-5

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  • DOI: https://doi.org/10.1007/s11746-003-0819-5

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