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A new reducing agent for nitrostyrenes: bakers yeast!
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Author Topic: A new reducing agent for nitrostyrenes: bakers yeast!
Labrat
Member posted 09-28-98 09:21 AM
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For all those people who can't find sodium borohydride, this is for you. First check out the following articles:
JCS Perk. Trans. 1: 501 ('98)
Aus. J. Chem. 49: 1257 ('96)
JOC 54: 1802 ('89)
Heterocycles 37: 553 ('94)
In these articles, bakers yeast is used to reduce b-nitrostyrenes to b-nitrophenethanes. These latter compounds can easily be reduced to the amines in at least 90% yield by a simple aluminum amalgam reduction. So this is an alternative 2-step nitrostyrene reduction, using easy-to-get chemicals!
The reaction conditions to get the best yields are as follows:
1 mmol nitrostyrene substrate
11 g yeast
0.8 ml water per g yeast (8.8 ml)
50 ml light petroleum
A representative procedure from JCS Perk. Trans. 1: 501 ('98):
"0.3 g nitrostyrene (2 mmol), 22.13 g bakers yeast, 17.7 ml water and 200 ml light petroleum were stirred at room temp for 24 h. The solvent was removed by filtration and the yeast washed with 3x50 ml CH2Cl2. The filtrates were combined and evaporated in vacuo to give a residue of 2-nitro-1-phenylethane (0.216 g, 72% yield)."
This reaction is simplicity itself, doesn't use hard-to-get chemicals and can be scaled up to bathtub size. The yield is pretty much the same as when using NaBH4 as reducing agent, 65-75%. Isn't this great?! Lr/
quirks
Member posted 09-28-98 09:33 AM
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What's light petroleum?
Piglet
Member posted 09-28-98 10:08 AM
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LR: Fucking hell man! Are you on strong stimulants? The number of ideas/posts you have made recently is crazy.
Will this work with nitropropenes? This is an excellent post. Funny and serious all at once. Sweeet.
Best wishes,
Piglet
Labrat
Member posted 09-28-98 04:51 PM
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quirks: light petroleum is petroleum ether.
Pig: strong stimulants? Well, I think it's more due to the great ganja we have here lately!
This nice little procedure does indeed work on nitropropenes too. When nitrostyrene was substituted for nitropropene with the same reaction conditions, a 66% yield of 2-nitrophenyl-1-propene was obtained. Lengthening the reaction time could very well give better yields.
Great you like the post. Lr/
Rhenium
Member posted 09-28-98 07:48 PM
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Labrat,
You continue to do the Hive proud. This is a funny but great post. If I was to tell my freak friends that I used baker's yeast to reduce my nitro-styrene's, even they would look at me funny. Pity the molar ratios are so hugely different, (0.3g:22g) but that's not a real problem, yeast can be bought by the bag. What the hell is the mechanism I wonder, I going to go get those referencs today!
Yeast? Hmmmmm... I wonder if you could use Vegemite instead?
Take care,
Rhenium
Labrat
Member posted 09-29-98 09:41 AM
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Thanks! I admit, using bakers yeast as a reducing agent is very freakish, but I can't help picturing somebody performing this reaction in the jaccuzy (?)! And it's a nice alternative for NaBH4 too!
BTW, what is Vegemite? A brand of bakers yeast I presume. Lr/
Snidely Whiplash
Member posted 09-29-98 12:20 PM
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"He just smiled and gave me a Vegemite sandwich"
- "Down Under" by Men At Work, circa ~1982
labgrrrl
Member posted 09-29-98 08:27 PM
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Vegemite is a yeast "spread" that you put on bread, toast, etc...it's kinda freaky stuff and not unlike Marmite. And, no you couldn't use it as a substitute for bakers yeast
I was exposed to such delights as a little grrrl...
-labgrrrl
Rhenium
Member posted 09-30-98 08:01 AM
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I was just kidding about the Vegemite, but I did get those papers, very interesting...
Ah, the ingenuity of chemistst (real or clandestine) never ceases to amaze me.
Labgrrl, where were you when you were exposed to the deights of Vegemite? I'm still in Vegemite Land myself...
"The worlds richest source of Vitamin B!"
Take care,
Rhenium
Labrat
Member posted 09-30-98 09:43 AM
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Shit, I think I know what you mean with Vegemite. I don't know anymore what it's called around here. I do remember the intense gory salty taste and the fact that it looks like road tar. And yes, it contains vitamines B (but so do vitamin pills).
But no more questions on the bakers yeast reduction? Great, that means I've explained it clear and simple the first time. Lr/
Piglet
Member posted 10-12-98 09:27 AM
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US Patent 4,106,986 describes epoxide formation from alkenes.
Labrat
Member posted 10-13-98 09:28 AM
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"The production of epoxide from .alpha.-olefin or .alpha.,.omega.-diene using an epoxide producing microorganism that belongs to Nocardia genus...".
In this method a bacteria of the Nocardia genus is used. I've no idea where to find a batch of these microorganisms. You know where Piglet? Lr/
Piglet
Member posted 10-13-98 10:05 AM
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I hunted on the net. Apparently they are EVERYWHERE in the enviroment. Getting a PURE source, I'm not sure. Anyone?
Labrat
Member posted 10-15-98 10:23 AM
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Maybe a biologist could tell us how to select the proper bacteria genus with the right medium. But I'm no biologist, so I still ain't got a clue. Lr/
NectarBoy
unregistered posted 10-26-98 05:43 PM
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You would need to find a source,get a sample and grow it in plates of nutrient agar,then you would have to distinguish between the organisim you want and the other ones you dont want.Well,Ill read more on it an get back to all you cats
gyrogearloose
Member posted 11-09-98 05:57 AM
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I looked in my trusty Merck index and found this is an old method, not new, the yeast is there under yeast, but it really does work...
I think everyone should buy a copy and read before posting here, I felt more confident after. It has so much info.
For instance all the talk of peonut oil and cotton seed oil, both are listed as solvents for aids in pharm. work. Given this I didcided to try to distill with the aid of peanut oil and then cotton seed oil, dude, My best yeild ever for mdp2p after the formic crap.
Bozakium
Member posted 11-10-98 09:27 PM
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Will other yeasts work? Could nitrostryenes be reduced, not in vacuo but in vaguo if one's wife had a yeast infection?
Labrat
Member posted 11-12-98 10:07 AM
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First recovering that yeast from the yeast infected place with your tongue! Then give it a try, who knows, it might work!
dpHarma
Member posted 11-15-98 02:01 AM
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gyro
please post some details of the use of peanut oil after performic!
Thanks
dpHarma
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