Isomerization of alkyl branched alkynoic acids

1986 ◽  
Vol 64 (3) ◽  
pp. 457-463
Author(s):  
Suzanne R. Abrams
Keyword(s):  
Alkali Metal ◽  
Triple Bond ◽  
Dienoic Acid ◽  
Methyl Branch ◽  
Metal Amides ◽  
Cis And Trans ◽  
Acetylenic Acids ◽  
Moderate Yield

Acetylenic acids are isomerized by alkali metal amides of 1,3-diaminopropane to 3,5-dienoic acids. An acid with a methyl branch at C-3 separating the carboxyl from the triple bond is rearranged to a mixture of the terminal alkynoic acid and two isomeric 3,5-dienoic acids. The corresponding 4-methyl compound affords the terminal alkynoic acid, one 3,5-dienoic acid, and two cyclized products, cis- and trans-3-methyl-5-(octylidene)-1-cyclopentanecarboxylic acids. Propargylic acids branched at C-5 and C-6 are rearranged to the appropriately substituted 3,5-dienoic acids in moderate yield.

Alkyne isomerization reagents: mixed alkali metal amides

1984 ◽  
Vol 62 (7) ◽  
pp. 1333-1334 ◽  
Author(s):  
Suzanne R. Abrams
Keyword(s):  
Alkali Metal ◽  
Triple Bond ◽  
Lithium Salts ◽  
Metal Amides ◽  
Mixed Alkali ◽  
Methylene Chain ◽  
Sodium And Potassium

Addition of sodium and potassium alkoxides, particularly potassium tert-butoxide, to the lithium salts of either 1,2-diaminoethane or 1,3-diaminopropane afford alkyne isomerization reagents that effect triple bond migration to the end of a methylene chain under milder conditions and in higher yield than do previously reported reagents.

scholarly journals Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali‐Metal Amides under Air

2020 ◽  
Vol 59 (43) ◽  
pp. 19021-19026 ◽  
Author(s):  
Florian F. Mulks ◽  
Leonie J. Bole ◽  
Laia Davin ◽  
Alberto Hernán‐Gómez ◽  
Alan Kennedy ◽  
...  
Keyword(s):  
Alkali Metal ◽  
Metal Amides

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

1983 ◽  
Vol 61 (6) ◽  
pp. 1073-1076 ◽  
Author(s):  
Suzanne R. Abrams ◽  
Donato D. Nucciarone ◽  
Warren F. Steck
Keyword(s):  
Sex Pheromone ◽  
Alkali Metal ◽  
Sodium Salt ◽  
Triple Bond ◽  
Lithium Salt ◽  
Terminal Position ◽  
Sodium Salts ◽  
Triple Bonds ◽  
High Yields ◽  
Insect Sex

The 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.

Synthesis and Structures of Alkali Metal Amides Derived from the Ligands [N(SiMe2Ph)(SiMe3)]−, [N(tBu)(SiMe3)]−, [N(Ph)(2-C5H4N)]−, and [N(2-C5H4N)2]−

2003 ◽  
Vol 2003 (18) ◽  
pp. 3391-3400 ◽  
Author(s):  
Floria Antolini ◽  
Peter B. Hitchcock ◽  
Alexei V. Khvostov ◽  
Michael F. Lappert
Keyword(s):  
Alkali Metal ◽  
Metal Amides

Titanium Carbene Complexes Stabilized by Alkali Metal Amides

2019 ◽  
Vol 58 (6) ◽  
pp. 1833-1837 ◽  
Author(s):  
Hassan Osseili ◽  
Khai‐Nghi Truong ◽  
Thomas P. Spaniol ◽  
Laurent Maron ◽  
Ulli Englert ◽  
...  
Keyword(s):  
Alkali Metal ◽  
Carbene Complexes ◽  
Metal Amides

Enhancement of the initial hydrogenation of Mg by ball milling with alkali metal amides MNH2(M = Li or Na)

2015 ◽  
Vol 44 (38) ◽  
pp. 16694-16697 ◽  
Author(s):  
Hailiang Chu ◽  
Shujun Qiu ◽  
Lixian Sun ◽  
Jacques Huot
Keyword(s):  
Alkali Metal ◽  
Ball Milling ◽  
Metal Amides

The addition of 4 wt% of MNH2(M = Li, Na) to pure Mg by ball milling greatly enhances the first hydrogenation (activation). Under 2 MPa of H2at 608 K, the best activation performance was achieved with the NaNH2additive.

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