The rearrangement of fatty cyclopropenoids in the presence of boron trifluoride | Zendy

Gilkison Ian S. | Zendy; Shone Geoffrey G. | Zendy

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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.

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