posted 11-04-98 06:04 AM         

To a ice-cooled solution of 64.8g (0.20mol) of Hg(NO3)2 in 100ml MeCN 16.8g (0.20mol) of 1-hexene are slowly added keeping the temp below 30°C. The clear yellow solution is stirred for 1hr at RT. With ice-cooling 200ml 3N NaOH are added, followed by a solution of 3.80g (0.10mol) of NaBH4 in 200ml 3N NaOH. Again stir for another hour.
Decant the aq/organic layer leaving the elemental Hg behind, saturate the aq. layer with NaCl and extract with Et2O (2*100ml). The extracts are dried with Na2SO4, the solvent removed and the residue distilled. 22.8g (80%) amide, bp (1.6 torr) 93-96°C.

Ref: JACS 91, 5647 (1969)

posted 11-05-98 04:51 PM         

Please elaborate on your comments. I am familiar with your first book. The comments on anhydrous mercuric nitrate do seem to be a problem, but I'd like to know what other concerns you have with the method. I never see anyone here at The Hive speak of this Markovnikov amination. That's a shame because with a little work it might prove to be a method for which little money or equipment is neccessary. I'd really appreciate it if you would indulge me in a discussion of this method.

thanks in advance,

posted 11-08-98 01:29 PM         

Thanks for the info. Could you please give a reference for this? I had heard that this method might work (as I know it works for many monohydrates) but have never found any references to dehydration of this particular Hg salt. I would soooooo appreciate this. Being able to get a definitive ref on this would make my millenium!

Thanks,