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Topic: Synthesis of (E,E)-1,4-diphenyl-1,3-butadiene with the Horner-Wadsworth-Emmons  (Read 10508 times)

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Offline nj_bartel

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Synthesis of (E,E)-1,4-diphenyl-1,3-butadiene with the Horner-Wadsworth-Emmons
« on: February 26, 2009, 10:00:38 PM »
I'm not sure if I'm just being blind, but I'm not seeing how I can do this.  Wiki (http://en.wikipedia.org/wiki/Horner-Wadsworth-Emmons_reaction) is the reference I'm using to attempt to solve it.  This isn't a reaction we've been taught - it's just an end of section organic lab question.  Any tips on the reagents used would be great.

Thanks
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Offline James Newby

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Re: Synthesis of (E,E)-1,4-diphenyl-1,3-butadiene with the Horner-Wadsworth-Emmons
« Reply #1 on: February 27, 2009, 01:11:00 PM »
I had a lecture on this just last week! What are your starting materials? If you dont know what they are can you give a reasonable guess as to what you would use?

CLUE Horner Wadsworth Emmons is the same as a wittig reaction, just gives different stereochemical outcome
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4th year undergraduate at the University of Sheffield

Offline nj_bartel

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Re: Synthesis of (E,E)-1,4-diphenyl-1,3-butadiene with the Horner-Wadsworth-Emmons
« Reply #2 on: February 27, 2009, 06:25:38 PM »
 http://img147.imageshack.us/my.php?image=orgquestionk.jpg

is what I come up with.  I don't know any ester cleavage reactions to get the desire product =/
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Offline azmanam

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Re: Synthesis of (E,E)-1,4-diphenyl-1,3-butadiene with the Horner-Wadsworth-Emmons
« Reply #3 on: February 27, 2009, 06:41:38 PM »
looks fine... leave off the ester.  all you need is an electron withdrawing group.  phenyl groups are acceptable electron withdrawing groups for HWE olefination.  just sub out the ester for a proton.
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Offline nj_bartel

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Re: Synthesis of (E,E)-1,4-diphenyl-1,3-butadiene with the Horner-Wadsworth-Emmons
« Reply #4 on: February 27, 2009, 06:51:26 PM »
Ah ok, wasn't sure of the EWG strength necessary, thanks.
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