Alkyne isomerization reagents: mixed alkali metal amides

1984 ◽  
Vol 62 (7) ◽  
pp. 1333-1334 ◽  
Author(s):  
Suzanne R. Abrams

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.

1986 ◽  
Vol 64 (3) ◽  
pp. 457-463
Author(s):  
Suzanne R. Abrams

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.


2021 ◽  
Vol 123 ◽  
pp. 108363
Author(s):  
Ting Zhang ◽  
Jing-Jing Zheng ◽  
Shi-Chao Cheng ◽  
Jun-Wei Feng ◽  
Chun-Yan Bai

2001 ◽  
Vol 16 (1) ◽  
pp. 127-131 ◽  
Author(s):  
A. Bartelt ◽  
S. Minemoto ◽  
C. Lupulescu ◽  
Š. Vajda ◽  
L. Wöste

2019 ◽  
Vol 58 (9) ◽  
pp. 5949-5955 ◽  
Author(s):  
Qian Wang ◽  
Fei Yang ◽  
Xing Wang ◽  
Jing Zhou ◽  
Jia Ju ◽  
...  

Author(s):  
T. Nurakhmetov ◽  
◽  
Zh. Salikhodzha ◽  
M. Dolomatov ◽  
A. Zhunusbekov ◽  
...  

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

1983 ◽  
Vol 61 (6) ◽  
pp. 1073-1076 ◽  
Author(s):  
Suzanne R. Abrams ◽  
Donato D. Nucciarone ◽  
Warren F. Steck

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.


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