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Chemistry of epoxy compounds. xxii. preparation of some long‐cham 2‐oxazolidones
Author(s) -
Dyen Martin E.,
Swern Daniel
Publication year - 1968
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/bf02667102
Subject(s) - chemistry , isocyanate , moiety , methyl iodide , catalysis , polymer chemistry , organic chemistry , iodide , epoxy , epoxide , lithium amide , lithium iodide , lithium (medication) , polyurethane , enantioselective synthesis , medicine , electrode , endocrinology , electrolyte
Long‐chain aliphatic compounds containing the 2‐oxazolidone moiety have been prepared from cis ‐ and trans‐ 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.