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Chemistry of epoxy compounds. xxii. preparation of some long-cham 2-oxazolidones

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Journal of the American Oil Chemists’ Society

Abstract

Long-chain aliphatic compounds containing the 2-oxazolidone moiety have been prepared fromcis- andtrans- 9 octadecene, methyl oleate, and elaidate, oleyl and elaidyl alcohols, and several long-chain terminal epoxides. The 2-oxazolidones prepared are substituted in the 4-, 4,5-, or 3,5-positions. The first two groups of oxazolidones are obtained by pyrolysis of β-iodocarbamates, prepared from terminal and internal monoun-saturated compounds respectively by the addition of iodine isocyanate and by reaction with meth-anol. The last group is prepared by heating ter-minal epoxides with organic isocyanates in DMP containing a catalytic quantity of tetramethyl-ammonium iodide or lithium chloride. Structures have been confirmed by elemental and spectral analysis.

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Authors and Affiliations

  1. Fels Research Institute and Department of Chemistry, Temple University, 19122, Philadelphia, Pennsylvania

    Martin E. Dyen

  2. Smith, Kline, and French Laboratories, Philadelphia, Pa.

    Daniel Swern

Authors
  1. Martin E. Dyen
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  2. Daniel Swern
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Recent work has shown that the ring closure is stereoselective, not stereospecific.

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Dyen, M.E., Swern, D. Chemistry of epoxy compounds. xxii. preparation of some long-cham 2-oxazolidones. J Am Oil Chem Soc 45, 325–330 (1968). https://doi.org/10.1007/BF02667102

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  • DOI: https://doi.org/10.1007/BF02667102

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