Poster 23 (fao Steve Marsden)

Jo Sweeney (sweeneyjb@siva.bristol.ac.uk)
Tue, 20 Jun 95 09:07:21 0000

Hi Steve, thanks for the comment. The point you've made is a good one and we do use different
conditions in the two selenenylation reactions- with the phenylglycine derivative we used only CSA
monohydrate as water source, whereas in the acetoxy case we used water. This probably leads to a
change in rate of the reaction, rather than a completely different set of events, but I share your
non-panoramic knowledge of organoselenium chemistry! We have not investigated the reactions of the
substrates under the vice-versa conditions, primarily because there's no one working on the project,
but there are a lot of simple reactions we could do to sort out exactly what's going on. In fact, the
reactions are so obvious even I could successfully execute them, but as I said to Jonathan Goodman
yesterday, the problem with obvious reactions is that they take just as long to do as smart ones!
I'd be interested to know the details of your PhSeOH problems, by the way, but I think that if we
were seeing addition of that species to the alkene we would also see it in the aminoester reaction,
since CSA should enhance formation of PhSeOH from NPSP in the presence of water. Shouldn't it? (one
of the problems about this conference is that chemical points you could comfortably and confidently
make in the bar at the end of a conference session become rather more intimidating when you know that
80 intelligent people are eavesdropping on your conversation!).
Every comment people have made has been a great help to my understanding of these observations and I
think we're probably getting into good shape to do the most rational serquence of reactions I've ever
given to a student! Do you think I should put all ECTOC contributors's names on the paper?!
Thanks for the comment Steve, and let me know about the PhSeOH shenanigens.
Jo

ECTOC-1. Conference home page: http://www.ch.ic.ac.uk/ectoc/ using
Netscape, Mosaic, etc.
E-mail discussions: http://www.ch.ic.ac.uk/hypermail/ectoc/
To unsubscribe from this list, send the message UNSUBSCRIBE ECTOC to
listserver@ic.ac.uk