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Formation of a cis alkane from a trans alkene

  1. Nov 20, 2011 #1
    1. The problem statement, all variables and given/known data

    Create cis-1,2-epoxy-1-phenylhexane from (E)-1-phenyl-1-hexene

    2. Relevant equations



    3. The attempt at a solution

    My teacher asked for two ways to create this and I think I've got the first.

    The first way was by treating (E)-1-phenyl-1-hexene with H2 and poisoned Pd in Ethanol. This creates a Cis product and then I react it with water and heat (E1 reaction) to form back an alkene but a cis alkene. Then I reacted it with peroxy acid in THF to form the product.

    I'm unsure of the second way of creating this, but my teacher told us a hint and he said to look at problem 10.48 in our book. I've looked at the solution manual and they reacted the CIS alkene with Br2 and H2O and the epoxy formed by deprotonating the hydrogens on the water that attached to the alkene. In this reaction, however, a CIS starting material formed a CIS product which doesn't help me since I"m trying to form a CIS from a TRANS.
     
  2. jcsd
  3. Nov 23, 2011 #2

    chemisttree

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    That didn't stop you from converting the trans alkene first to a cis alkene in your first answer...

    You allowed to use Jacobsen or Shi methods?
     
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