9-Octadecene, 1-bromo-, (9Z)- → (Z)-9-Tricosene
Reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20]([Mg]Br)[CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In contrast, the reaction of one equivalent of oleyl bromide with 1.2 equivalents of amyl-magnesium bromide and 5% m/m lithium dichlorocuprate in tetrahydrofuran at -25° to -15° and using a procedure identical to that of Example 7 gave about 80% conversion to crude Z-9-tricosene. The remainder of the product is Z-1,9-octadecadiene.