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Isomerization of acetylenic acids with sodium salt of 1,2-diaminoethane: a one step synthesis of megatomoic acid

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1139/v82-182
AuthorSearch for: 1
Affiliation
  1. National Research Council of Canada. NRC Plant Biotechnology Institute
FormatText, Article
Abstract
A number of isomeric tetradecynoic acids were isomerized with the sodium salt of 1,2-diaminoethane. Isomers having the triple bond near the carboxyl group rearranged to E,Z-3,5- and E,E-3,5-tetradecadienoic acids (1 and 2), the former compound being the sex pheromone of the black carpet beetle. Isomers having the triple bond closer to the terminus of the chain afforded some 13-tetradecynoic acid along with 1 and 2. Delocalized anions 12 and 13 are thought to contribute to the formation of 1 and 2.
Publication date
PublisherCanadian Science Publishing
National Research Council of Canada. NRC Research Press
In
  • Canadian Journal of Chemistry 60, no. 10 (April 1982): 1238–1243.
LanguageEnglish
Peer reviewedYes
NRC numberNRCC 20049
NPARC number21273764
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Record identifier62fc5262-99fe-4cc6-8a65-b8db58e7915e
Record created2015-01-20
Record modified2023-10-06
Date modified: