Some alkali metal alkyl amides as alkyne isomerization reagents: selective isomerization of one triple bond of a diynol

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DOIResolve DOI: http://doi.org/10.1139/v83-189
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
Volume61
Issue6
Pages10731076; # of pages: 4
AbstractThe lithium and sodium salts of 1,2-diaminoethane, 1,3-diaminopropane, n-butylamine, and the lithium salt of isobutylamine were studied as potential reagents for isomerization of triple bonds in alkyn-1-ols. The sodium salts of the diamines afforded high yields of the ω-alkyn-1-ol. Somewhat surprisingly, the sodium salt of n-butylamine also effects isomerization to the terminal position. The lithium salt of 1,3-diaminopropane gave the highest conversion of 2- to 3-alkyn-1-ol. A novel, selective rearrangement of one triple bond of a diynol, a 2, ω- to 3, ω-diyn-1-ol isomerization, was incorporated into a synthesis of the insect sex pheromone 3,13-octadecadienol acetate.
Publication date
LanguageEnglish
AffiliationNRC Plant Biotechnology Institute; National Research Council Canada
Peer reviewedYes
NRC number20881
NPARC number21273766
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Record identifiere738b1b7-5d6c-4090-bf1a-5715cc277d54
Record created2015-01-20
Record modified2016-05-09
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