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Heavily brominated and highly unsaturated derivatives of jojoba oil
Author(s) -
Shani Ar
Publication year - 1988
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/bf02542414
Subject(s) - bromine , halogenation , allylic rearrangement , chemistry , organic chemistry , hydrolysis , derivative (finance) , wax , medicinal chemistry , catalysis , financial economics , economics
Two hexabromojojoba isomers were prepared by bromine addition to bromo‐olefinic and bromoallylic derivatives, and an octabromojojoba derivative was prepared from jojobatetraene. Bis‐allylic bromination of jojoba wax or monoallylic bromination of jojobatetraene, both followed by HBr elimination, yielded jojobahexaene, which has two conjugated triene units on both parts of the ester. Bromine addition to jojobahexaene yielded dodecabromojojoba, which was unstable toward hydrolysis in water‐decalin mixture at 120C., This is in contrast to the relative stability of the octabromojojoba under these conditions.