I think these are all different. The substructure in question here is
R1O/P(=O)=C/R2
I think I managed to convince myself that stereochemistry here is
reasonable by rewriting the structure as:
R1O/[P+]([O-])=C/R2
but I would still certainly like some real examples.
-greg
On Fri, Mar 11, 2016 at 10:38 AM, Giuseppe Marco Randazzo <
gmranda...@gmail.com> wrote:
> An example can be the case of this isomerism is given by
> triphenylphosphorane (Witting reagents).
>
> Here i give to you some publications were can find a clear publication
> about cis/trans isomerism and the importance.
>
> [1] Conformation isomerism and coupling constants of formylmethylene
> triphenylphosphorane (C6H5)3P=CH-CHO
> Comptes Rendus des Seances de l'Academie des Sciences, Serie C:
> Sciences Chimiques (1970), 270, (21), 1747-9.
>
> [2] Structural and conformational analysis of 2-triphenylphosphoranylidene
> succinic acid derivatives by 1H, 13C and 31P one and two dimensional NMR
> spectroscopy and molecular modelling
> Radu Bacaloglu, Andrei Blaskó, Clifford A. Bunton, Giorgio
> Cerichelli, Fernando Castaneda and Enrique Rivera
> J. Chem. Soc., Perkin Trans. 2, 1995, 965-972
> DOI: 10.1039/P29950000965
>
>
> [3] Favoured conformations of methyl isopropyl, ethyl isopropyl,
> methyl tert-butyl, and ethyl tert-butyl
> 2-(triphenylphosphoranylidene)malonate
>
> [4] Conformations of diester triphenylphosphonium ylides with an ylidic
> ester or keto and ester ylidic groups
>
>
> Best regards
> Marco
>
>
>
>
>
>
>
> On 11 Mar 2016, at 10:12, Greg Landrum <greg.land...@gmail.com> wrote:
>
>
> On Fri, Mar 11, 2016 at 10:05 AM, Jean-Marc Nuzillard <
> jm.nuzill...@univ-reims.fr> wrote:
>
>>
>> Le 11/03/2016 05:11, Greg Landrum a écrit :
>>
>>
>> Here's a question for the chemists in the group: do we need to be
>> concerned about representing the stereochemistry of the P=C bond in
>> substructures like O=P(/O)=C/C under normal circumstances?
>>
>>
>> It has a meaning to write that the configuration of the P=C bond is Z or
>> E.
>>
>
> If this is the case, I'd love to add some real examples to the test suite.
> Can you point me to some examples (or a paper/web page talking about the
> topic)?
>
> -greg
>
>
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