Abstract
Current studies on odor thresholds of hydrocarbons autoxidatively derived from fats required the preparation of 1,3- and 2,4-nonadienes. The pyrolysis of 3-acetoxy-1-nonene (I) and 4-acetoxy-2-nonene (II) was investigated as a route to 1,3- and 2,4-nonadienes, respectively. The acetates were pyrolyzed over pyrex helices at 400 C. Distilled pyrolyzates were characterized by mass, UV, IR, and NMR spectroscopy, along with gas chromatography. Since II gave approximately a 50∶50 mixture of the 1,3- and 2,4-isomers, an earlier observation was confirmed that allylic esters may rearrange before elimination. Ester I gave about 85% of the 1,3-isomer and 15% of the 2,4. Presumably the 2,4-isomer arises from thermal rearrangement. In pyrolysis, both I and II give conjugated products almost exclusively. UV spectroscopy shows ε values in the 24,000 to 28,000 range.
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North. Market. Nutr. Res. Div., ARS, USDA.
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List, G.R., Evans, C.D., Selke, E. et al. Pyrolysis of some acetoxynonenes. Lipids 6, 635–640 (1971). https://doi.org/10.1007/BF02531520
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DOI: https://doi.org/10.1007/BF02531520