Abstract
The 1-azirine derivatives ofcis-9-octadecene and methyl oleate have been prepared, and some of their reactions have been studied. The preparation of these novel fatty acid derivatives was accomplished in a three-step synthesis with good overall yields. Addition of the electrophile IN3 to the olefin yielded the β-iodoazide derivatives of octadecane and stearic acid. Treatment of the latter compounds with base resulted in dehydrohalogenation and gave the vinyl azides. Solution photolysis of the vinyl azides yielded the 1-azirine derivatives. Reduction of the 1-azirines with metal hydrides gave the known epimino derivatives of octadecane and octadecanol. Other reducing agents were unsuccessful in preserving the three-membered ring. Reaction with acids caused the dimerization of the 1-azirines with formation of tetrasubstituted pyrazines. The 1-azirines were attacked by acid chlorides and hydrochloric acid to give chlorinated amides as principal products.
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E. Market. Nutr. Res. Div., ARS, USDA.
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Foglia, T.A., Barr, P.A. & Maerker, G. Preparation and reactions of fatty acid azirines. J Am Oil Chem Soc 49, 414–418 (1972). https://doi.org/10.1007/BF02582524
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DOI: https://doi.org/10.1007/BF02582524