Preparation and characterization of methyl 11-amino-(N-P-toluenesulfonyl)-9-E-octadecenoate and methyl 8-amino-(N-P-toluenesulfonyl)-9-E-octadecenoate

JAOCS, Journal of the American Oil Chemists' Society

Volumn 74, Issue 3, 1997, Pages 229-234

  Herron, Barry F ^a   Bagby, Marvin O ^a   Isbell, Terry A ^a   Byrdwell, Wm Craig ^a   Plattner, Ron ^a   Weisleder, David ^a  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

Allylic amination; Bis(N p toluenesulfonyl) sulfodiimide; Methyl 11 amino (N p toluenesulfonyl) 9 E octadecenoate; Methyl 8 amino (N p toluenesulfonyl) 9 E octadecenoate; Methyl oleate.

Indexed keywords

AMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MELTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SULFUR COMPOUNDS; THIN LAYER CHROMATOGRAPHY; UNSATURATED COMPOUNDS;

ALLYLIC AMINATION; METHYL OLEATE;

NITROGEN COMPOUNDS;

EID: 0031099789     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-997-0128-7     Document Type: Article

References (20)

1. Knothe, G., D. Weisleder, M.O. Bagby, and R.E. Peterson, Hydroxy Fatty Acids Through Hydroxylation of Oleic Acid with Selenium Dioxide//tert-butylhydroperoxide, J. Am. Oil Chem. Soc. 70:401-404 (1993).
2. Turk, A., M. Lebanon, and P.D. Boone, Oxidized Olefin Liquids, U.S. Patent 2,469,059 (1949).
3. Naudet, M., and E. Ucciani, Allylic Halogenation and Oxidation of Unsaturated Esters, in Topics in Lipid Chemistry, edited by F.D. Gunstone, John Wiley & Sons, New York, 1971, Vol. 2, pp. 99-158.
4. Kresze, G., and H. Münsterer, Bis(methoxycarbonyl) Sulfur Diimide, a Convenient Reagent for the Allylic Amination of Alkanes, J. Org. Chem. 48:3561-3564 (1983).
5. Singer, S.P., and K.B. Sharpless, Synthesis of dl-Gabaculine Utilizing Direct Allylic Amination as the Key Step, Ibid. 43:1448-1455 (1978).
6. Hayashi, T., A. Yamamoto, Y. Ito, E. Nishioka, H. Miura, and K. Yanagi, Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition-Metal Complexes. 8. Palladium-Catalyzed Asymmetric Allylic Amination, J. Am. Chem. Soc. 111:6301-6311 (1989).
7. Sharpless, K.B., T. Hori, L.K. Truesdale, and C.O. Dietrich, Allylic Amination of Olefins and Acetylenes by Imido Selenium Compounds, Ibid. 53:269-271 (1976).
8. Brimble, M.A., and C.H. Heathcock, Allylic Amination by the Lewis-Acid-Mediated Ene Reaction of Diethyl Azodicarboxylate with Alkenes, J. Org. Chem. 58:5261-5263 (1993).
9. Johannsen, M., and K.A. Jørgensen, Iron-Catalyzed Allylic Amination, Ibid. 59:214-216 (1994).
10. Shea, R.G., J.N. Fitzner, J.E. Fankhauser, A. Spaltenstein, P.A. Carpino, R.M. Peevey, D.V. Pratt, B.J. Tenge, and P.B. Hopkins, Allylic Aelenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines, Ibid. 57:5243-5251 (1986).
11. Lorenz, O., and C.R. Parks, Ozonides from Asymmetrical Olefins. Reaction with Triphenylphosphine, Ibid. 30:1976-1981 (1965).
12. Benton, F.L., A.A. Kiess, and H.J. Harwood, Ozonolysis as a Method for Establishing the Positions of Olefinic Linkages, J. Am. Oil Chem. Soc. 36:457-460 (1959).
13. Privett, O.S., and E.C. Nickell, Studies on the Otonitation of Methyl Oleate, Ibid. 41:12-11 (1964).
14. Isbell, T.A., and R. Kleiman, Characterization of Estolides Produced from the Acid-Catalyzed Condensation of Oleic Acid, Ibid. 71:379-383 (1994).
15. Hori, T., S.P. Singer, and K.B. Sharpless, Allylic Deuteration and Titration of Olefins with N-Sulfinylsulfonamides, J. Org. Chem. 43:1456-1459 (1978).
16. Isbell, T.A., R. Kleiman, and S.M. Erhan, Characterization of Monomers Produced from Thermal High-Pressure Conversion of Meadowfoam and Oleic Acids into Estolides, J. Am. Oil Chem. Soc. 69:1177-1183 (1992).
17. Bussas, R., and G. Kresze, En-reaktionen mis Schwefeldiimidenstruktur der En-Kumponente und Reaktivitat bei der Umsetzundy mit Ditosylschwefeldiimid, Liebigs Ann. Chem.: 629-649 (1980).
18. Alexander, L.R., and J.B. Justice, Fatty Acid Composition of Human Erythrocyte Membranes by Capillary Gas Chromatography-Mass Spectrometry, J. Chromatogr. 342:1-12 (1985).
19. Glaspy, P.E., R.A. Hancock, and B.S. Thyagarajan, Mass Spectral Rearrangements of 3-Arylsulphonyl-2-arylthiopropenes and N-(4′-arylsulphonyl-2′-butynyl)-N-(4″-arylthio-2″- butynyl)anilines, Org. Mass Spectrom. 20:281-287 (1985).
20. Sun, K.K., and R.T. Holman, Mass Spectrometry of Lipid Molecules, J. Am. Oil Chem. Soc. 45:810-817 (1968).