From: Glen Brizius (brizius$##$psc.sc.edu)
Date: Tue Apr 18 2000 - 01:17:58 EDT
Hello, all. I am trying to synthesize compounds with the following
molecular structure: RBrC(double bond)CBrR, where the halogens are
preferably trans to each other. An example would be
trans-2,3-dibromo-2-butene, which would have pendant methyl groups.
Ideally I'd like to have control over the identity of the alkyl groups,
which would hopefully come from commercially available precursors (alkyl
bromides, alcohols, aldehydes, etc).
So far I've tried transforming trans-2,3-dibromo-1,4-dihydroxy-2-butene
into the 1,2,3,4-tetrabromo-2-butene with PBr3, followed by reaction
with alkyl Grignard reagents. However, this gives me a complex mixture
of (allylic rearranged) products. While I can make the dialkoxy
versions easily, they are not any good for my particular reaction, they
have to be alkyl.
Does anyone have any experience in this type of synthesis that would
like to share? All opinions gratefully :) accepted via email. Thanks
in advance!
Glen Brizius
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