Al/Hg on ketoximes

[Antibody2]

Did you apply external heat when you tried it without acid? no, the trials without acids were early on while i was still triing to make the THF solvent system work, refluxing THF was something i triied to avoid.

and yes the foil was consumed (very slowly in the trial without water or acid), but i don't know what the product(s) formed was except that is was nothing that would form an HCl salt.

as far as the last question, i maintain that the amount of base used in work-up is irrelevant to the yeild of the reduction providing that a ph of at least 10 was/is acheived. Beyond that who can say for sure? Why don't you try using 7.5 equivalents of Al, there was no drop in yeild at those ratios using HOAc, and then we will have a real apple to apple comparison.

[hypo]

as was pointed out again and again, protons are needed for
this reaction. in acidic solution, per definition, there's more
proton activity, so maybe this makes the reaction run at lower
temperature? ok, proton takeup is not the limiting step, but
there's stranger things, so why not. i doubt that the reaction of
dil. AcOH with Al gives the heat to drive the reaction. iirc
small-scale AcOH/Al/Hg reactions weren't noticeably exothermic
and yet gave acceptable yields. anyway, if it's true that acidic
solution lower the temperature needed for an Al/Hg reduction,
then that's a damn good thing to know, imho.

[Antibody2]

This is an apology directed at Chromic, for the ill teatment he recieved at my hands at the beginning of this thread. I'm not sure why it took me as long as this to author this retraction. Probably because I've spent the interim trying to rationalize my non-compliance with my own value system.

As long as I've been a member here, the ideas, dumb ideas, experiments and questions I've posted have for the most part been met with with encouragment, at worst I've received patient explanations why some of my dumber ideas wouldn't work. The result of this positive reinforcement is that I have never hesitated to post a thought or an idea, a suggestion or question for fear of the response i might receive. It probably also follows that lacking this support/encouagment i may have been inhibited in some of my experimentation, and that i may have had fewer sucesses under my belt.

Rhodium and Strike have done alot to foster an atmosphere condusive to sharing, experimentation and progress. We as a collective have benefited immensly as a result of the sharing that happens here at the hive. When i brought my beligerent ego to the table that day, I acted out of self interest and emperiled the wonderful atmoshpere that exists here. If bees had to fear the kind of response that i gave to Chromics queries every time they posted, the hive would disintegrate and progress here would stop. We would become a historical snapshot.

So, here is my apology to Chromic and the rest of the hive for my loathsome behavior that day, may it never be repeated. Long live the hive.

Crow isn't half bad with a little Worchestershire sauce.
Ab2

[Rhodium]

Read the link posted in

Post 480400 (missing)

(indium: "the hive as gift culture?", The Couch) - it explains a lot about the psychological reactions which may result from our meritocratic society based upon a gift economy for the sharing of experimental results and methods. A very good read, I'd say.

[Chromic]

Apology accepted. I don't know how many times I've been wrong and admitted it here, but I know it's more than a handful. I do see how my initial post provided an emotional spark, and I do apologize about that. Long live the kind-natured members of the Hive.