ORGLIST: Re: PhI=NSes

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From: Sengen Sun (sengensun$##$yahoo.com)
Date: Wed Dec 01 2004 - 17:35:12 EST


Thanks to Graham and Maringati for valuable advices on
this compound.

I have tested the next step reaction without getting a
satisfactory H-1 NMR, as suggested by Maringati. And
it worked nicely. The answer is that experience is
more important than NMR in chemistry or NMR is not
needed sometimes-:)

Thanks again.

Sengen

--- Graham Cumming <G$##$ecosse.net> wrote:

> Hi
>
> I've never made this reagent but have used the
> N-tosyl version a number of
> times, and it is indeed a bit capricious.
>
> I think the most likely problem is acidic CDCl3; if
> you haven't already,
> filter your CDCl3 through 1 cm of basic alumina in a
> pipette before use.
>
> Alternatively, there are later procedures, also by
> Dauban and Dodd, for the
> in-situ preparation of the reagent from PhI=O and
> H2NSes (although in this
> case you have to make PhI=O, which is difficult to
> obtain dry).
>
> You could also try your reactions with PhI=NTs
> first, as this is pretty easy
> to make (I never bothered with NMR, it seems to be
> OK) and the reactions (if
> you haven't done them before) can take a bit of
> practise to get working OK.
>
> Good luck!
>
> Graham
>

--- Maringanti Krishna <maringanti9$##$yahoo.com> wrote:

> Dear Sun:
>
> You should try anhydrous CDCl3 without TMS! Or you
> could even try C6D6!
> But one thing: Cant you just carry-out the next
> reaction in the sequence and confirm the structure
> your product rather than this reagent?
> Krishna
>

                
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