Okay I will do my best to respond one by one but promise nothing as I was about to sleep and, in retrospect mistakenly, allow the affects of carisoprodol and clonazepam take their effect. But I will fight it off to try to make some clarifications. I might need to pick this up tomorrow but in all the textbooks I've ever read the Birch reduction was just like you described. It was a solvated electron provided by an alkali metal. In the ghetto clandestine arena lithium is used but the Birch is generally done with Sodium as an electron donor. Solvent is ammonia and the co-solvent, and this is where the difference comes in, is the use of some alcohol (generally EtOH). The difference is that the thing reduced is a conjugated double bond, as in a double bond in the resonance structure that is the phenyl ring.
"Birch Reduction
The Birch Reduction offers access to substituted 1,4-cyclohexadienes.I was unable to copy the image. I'm just not very knowledgeable when It come's to computes. But here's an excellent link to show you what I mean:
http://www.organic-chemistry.org/namedreactions/birch-reduction.shtmAnother good explanation occurs in wikipedia:
The Birch reduction is the organic reduction of aromatic rings with sodium and an alcohol in liquid ammonia to form 1,4-cyclohexadienes. The reaction was reported by the Australian chemist Arthur John Birch (1915–1995) in 1944.[1][2][3][4][5][6] This reaction provides an alternative to catalytic hydrogenation, which usually reduces the aromatic ring all the way to a cyclohexane (after the initial reduction to a cyclohexadiene, catalytic reduction of the remaining (nonaromatic) double bonds is easier than the first reduction).
Lithium and potassium can substitute for sodium, and alcohols are ethanol and tert-butanol.
An example is the reduction of naphthalene:[7]In an instance, if you add an alcohol to the reduction of ephedrine you will not get methamphetamine but some 1,4-dichydrcyclohexane derivative.
Notice that "Chem Guy" called his article "Birch-Like Reductions"
I have to admit to not having the concentration to read the whole thing just now but read the JOC article Chem Guy added and it states:
"... In the course of this paper we are reporting the effects of water and alcohols on the course of the [Li-amine] reduction." "We found that, in the presense of alcohol, the Li-amine combonation can be used quite sucessfully to form dihydro aromatics."In that experiment they used the typical Birch Reduction to reduce isopropylbenzene to 2,5 dihydroisoproplylbenzene.
Anyway, you are right about the KMnO4 but I have some thoughts on the matter I might add in the next post. As for the Birch, I might be splitting hairs here but I am under the understanding that it is always used to reduce conjugated double bonds. At least that's how it reads in every text I have ever read, even Vogel.
Moriarty
P.S. Note, the spelling mistakes were Chem Guy's, not my own
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