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Synthesis of Δ 2 ‐Isoxazoline fatty acid ester heterocycles
Author(s) -
Kenar James A.,
Erhan Sevim Z.
Publication year - 2001
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/s11746-001-0386-9
Subject(s) - nitrile , synthon , chemistry , triethylamine , regioselectivity , organic chemistry , sodium methoxide , yield (engineering) , cycloaddition , fatty acid methyl ester , fatty acid , catalysis , carbonylation , biodiesel , carbon monoxide , materials science , metallurgy
Fatty ester Δ ‐2 heterocycles were prepared in good yields and excellent regioselectivity from 1,3‐dipolar cycloaddition reactions between methyl 10‐undecenoate and nitrile oxides. This methodology provides convenient access to the methyl esters of margaric ( 4b ) and stearic ( 4c ) acids in 63–66% yield that contain the isoxazoline heterocycle between C‐10 and C‐12. These fatty heterocycle compounds are synthesized in a one‐pot sequence in which methyl 10‐undecenoate is used to trap the reactive nitrile oxide intermediates that are generated by reacting aldoximes with aqueous sodium hypochlorite and a catalytic amount of triethylamine or by directly reacting hydroximic acid chlorides with a stoichiometric amount of base. The fatty ester Δ 2 ‐isozazoline heterocycles represent a versatile synthon that may be useful to obtain oleochemicals with potentially new and interesting properties not easily accessible by other methods.