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Synthesis of GEM ‐dibromocyclopropanoid fatty esters using phenyl (tribromomethyl) mercury
Author(s) -
Jamal Sajid,
Ahmad Ishtiaque,
Iqbal Jawaid,
Ahmad Mashood
Publication year - 1984
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/bf02540809
Subject(s) - chemistry , mercury (programming language) , double bond , methyl group , medicinal chemistry , organic chemistry , stereochemistry , group (periodic table) , computer science , programming language
The gem ‐dibromocyclopropanation of naturally occurring unsaturated hydroxy fatty esters, methyl ricinoleate (I) and methyl isoricinoleate (II), has been undertaken to provide compounds which might have potential utility. Phenyl(tribromomethyl)mercury reacts only with the carbon‐carbon double bond of each substrate, leaving the OH group intact. The product, methyl 9,10‐dibromomethylene‐12‐hydroxyoctadecanoate (III) and methyl 12,13‐dibromomethylene‐9‐hydroxyoctadecanoate (IV), obtained from I and II, respectively, were characterized by elemental, infrared (IR) and nuclear magnetic resonance (NMR) analyses.