Base mediated dimerization of 2-tetradecynoic acid

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DOIResolve DOI: http://doi.org/10.1139/v83-423
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
Volume61
Issue11
Pages24492454; # of pages: 6
AbstractUnder the influence of the very strong base, the sodium salt of 1,2-diaminoethane in 1,2-diaminoethane, 2-tetradecynoic acid is converted to 3-tetradecynoic acid (35%) and a novel dimer 3. Compound 3 ((Z)-2-(1-dodecynyl)-3-undecyl-pent-2-en-1,5-dioic diacid) is isolated as the monomethyl ester 1 after treatment of the crude product with methanolic HCl. The structures of 1 and 3 are deduced from an X-ray crystallographic analysis of the dimethyl ester 2 obtained by reaction of 1 with diazomethane. The dimer 3 is thought to arise from Michael addition of the dianion 4 of 3-tetradecynoic acid with the sodium salt of 2-tetradecynoic acid.
Publication date
LanguageEnglish
AffiliationNRC Plant Biotechnology Institute; National Research Council Canada
Peer reviewedYes
Identifier22443
NPARC number21273767
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Record identifier038967f4-ade0-44fe-a087-2b9bc70c8c09
Record created2015-01-20
Record modified2016-05-09
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