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Isocyanates derived from fatty acids by the trimethylsilyl azide modification of the curtius rearrangement
Author(s) -
Washburne S. S.,
Peterson W. R.
Publication year - 1972
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02609201
Subject(s) - curtius rearrangement , trimethylsilyl azide , isocyanate , azide , chemistry , alkyl , trimethylsilyl , organic chemistry , fatty acid , polymer chemistry , medicinal chemistry , polyurethane
Five fatty acid chlorides—myristoyl (14:0), palmitoyl (16:0), linoleoyl (18:2), oleyl (18:1) and stearoyl (18:0)—were smoothly converted in a one‐pot, one‐step reaction to the isocynates with one less carbon atom in the alkyl chain by treatment with trimethylsilyl azide in aromatic solvents at 100 C. The yields were consistently greater than 70%, and NMR and IR spectra of the products were consistent with the assigned isocyanate structures.