scholarly journals Formation of an Isomeric Mixture of Dienynes Instead of a Diallene

Molbank ◽  
10.3390/m1133 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1133 ◽  
Author(s):  
Susanne M. Petrova ◽  
Leiv K. Sydnes

Attempts to convert 1,1,2,2,7,7,8,8-octaethoxyocta-3,5-diyne to a symmetric allene by reduction with lithium aluminum hydride failed. Instead reduction accompanied by isomerization occurred and afforded 1,1,2,7,8,8-hexaethoxyocta-2,6-dien-4-yne as a mixture of three isomers in 63% total isolated yield.

1973 ◽  
Vol 51 (13) ◽  
pp. 2102-2104 ◽  
Author(s):  
Donald G. Lee ◽  
James R. Brownridge

The reduction of ethyl phenylpropiolate by lithium aluminum hydride results in partial reduction of the triple bond to give trans-cinnamyl alcohol. If ethyl phenylpropiolate is reduced by LiAlD4 followed by work-up with acetone and H2O the product is the specifically labeled compound, trans-3-phenyl-2-propen-1-ol-1,1,2-d3. If the ester is reduced with LiAlH4 followed by work-up with acetone-d6 and D2O the product is trans-3-phenyl-2-propen-1-ol-O,3-d2. Oxidation of these two products by sodium ruthenate leads to formation of trans-cinnamic acid-α-d and trans-cinnamic acid-β-d, respectively.


1973 ◽  
Vol 9 (4) ◽  
pp. 503-506
Author(s):  
G. A. Golubeva ◽  
L. A. Sviridova ◽  
N. Yu. Lebedenko ◽  
A. N. Kost

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