ORGLIST: Curtius rearragement/GC-MS study

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From: Jonas Nilsson (jonni$##$ifm.liu.se)
Date: Thu Aug 03 2000 - 04:33:52 EDT

Hello.
I'm trying to do a curtius rearragement according to the following

MeOOC-R-COOLi + (PhO)2P(=O)N3 -> MeOOC-R-CON3 -> MeOOC-R-NH2
(in water/acetonitrile)
or
MeOOC-R-COOLi + (PhO)2P(=O)N3 -> MeOOC-R-CON3 -> MeOOC-R-NHBoc
(in tBuOH)

I cant spot anything on the TLC though so my thought was to analyse by
GC-MS. The starting material however will ofcourse not pass the column
so i need to derivitize it. What procedures are available and what are
the conditions? I was thinking about just adding Me3SiCl and then run
it. There are som considerations however.

Which is the order of reactivity with Me3SiCl in slightly basic solution
of the following functionalities:
tBuOH
H2O
-NH2
-COO(-) / -COOH

Any other suggestions?
/jN 

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