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The rearrangement of fatty cyclopropenoids in the presence of boron trifluoride
Author(s) -
Gilkison Ian S.,
Shone Geoffrey G.
Publication year - 1993
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/bf02545328
Subject(s) - boron trifluoride , methylene , chemistry , yield (engineering) , conjugated system , ring (chemistry) , boron , medicinal chemistry , molecule , alkyne , organic chemistry , catalysis , materials science , polymer , metallurgy
The destruction of the cyclopropenoid ring system of methyl 9,10 methyleneoctadec‐9‐enoate (methyl sterculate) with boron trifluoride etherate has been shown to give a complex mixture of products, including methyl esters of C 19 allenes (12%), a C 18 alkyne (11%) and a variety of C 19 and C 20 conjugated dienes containing either a methyl or methylene branch. The methylene group lost from the methyl sterculate reactant in the formation of methyl octadec‐9‐ynoate is incorporated into a second molecule of reactant to yield a mixture of methyl 9‐methylene‐ trans ‐nonadec‐10‐enoate and the 11‐methylene‐ trans ‐9‐isomer.