Lem2 (Hive Bee)
05-16-02 23:02
No 309554
      Grignard rxn in xylene  Bookmark   

I was browsing through Rhodium EXCELLENT site, when I stumbled upon this:
../rhodium/chemistry /grignard.notes.html

The part I was most intrigued with was this:
"Hydrocarbons. ...Tschelinzeff attempted the preparation of of Grignard reagents from a series of iodides (not specified) in benzene, both thiophene-free and thiophene contaminated, but noted no preceptible reaction after forty-eight hours at the boiling point. In xylene, he was able to prepare reagents from, ethyl, n-propyl, n-butyl, and n-amyl iodides without the use of a "catalyst".

My question is, would the methyl iodide work in a similar fasion? It has no mention in the document, positive or negative. I sure could use some MeMgI w/o all the nasty ether fumes/explosions!

He who makes a beast of himself gets rid of the pain of being a man.
 
 
 
 
    lugh
(Moderator)
05-17-02 01:46
No 309637
      References  Bookmark   

You might want to check out the original references, some are in the text of the document on Rhodium's page you cited. Some that have a bearing on your question that aren't are JCS 89 2262-73 (1906) and 119 1249-56 (1966), in the former a mixture of 250 ml thiophene free benzene, 1.5 methyl iodide and .3 grams of magnesium powder were boiled for several hours without any detectable reaction. They then added 3 grams of tribenzylphosphine oxide, and the clear liquid became cloudy and the magnesium started to dissolve and the expected reaction occured. The latter is a comparirive study featuring methyl iodide grignards in benzene, with a variety of ethers and sulfur analogs as catalysts. Chem Guy did well to bring this knowledge to the Hive, but to expect him to type in the whole article is asking a lot  smile
 
 
 
 
 
 
 
    hest
(Hive Addict)
05-17-02 11:30
No 309870
      Grignard  Bookmark   

Iff you use 1-3mole of ether (THF) to one mole Mg and then dry toluene as solvent, these reactions rum much easyer. The poin is more to raise the reactionstem than sustitute the ether.
 
 
 
 
    PrimoPyro
(Hive Prodigy)
05-17-02 11:34
No 309873
      Catalysis  Bookmark   

For many Grignard Reagents (but not all) anhydrous triethylamine will catalyze formation of the organomagnesium halide entity. It need only be present in very small percentages.

For some halides, though, quaternization occurs with addition of triethylamine, greatly hindering the reaction.

                                                  PrimoPyro

Vivent Longtemps La Ruche! How's my posting? Call 1-800-EAT-SHIT
 
 
 
 
    Lem2
(Hive Bee)
05-17-02 20:42
No 310031
      asdf  Bookmark   

it is true that is in the article, but what I was interested in was the formation of grignards WITHOUT a catalyst in dry xylene. the point of clandestine chemistry is to do things with as little stuff as possible, less stuff = less to catch. if one could make MeMgI/EtMgI w/o ether, and w/o trialkylamines, that would be a great step forward.

He who makes a beast of himself gets rid of the pain of being a man.
 
 
 
 
    hest
(Hive Addict)
05-17-02 21:54
No 310046
      ether  Bookmark   

ether(usual dimethylether) is the main part of disel start. you can get it at all tankstations. Spry some into your toluen and the reaction will bee much easyer to do.
 
 
 
 
    hsark
(Hive Bee)
05-30-02 20:33
No 316008
      Hey  Bookmark   

Shouldnt that be Diethyl ether or ethyl ether.

I think i like it!
 
 
 
 
    Osmium
(Stoni's sexual toy)
05-31-02 00:15
No 316069
      Dimethylether is a common propellant for all ...  Bookmark   

Dimethylether is a common propellant for all kinds of sprays.

I'm not fat just horizontally disproportionate.
 
 
 
 
    foxy2
(Distinctive Doe)
05-31-02 21:25
No 316379
      you sure?  Bookmark   

I have never seen dimethylether list on anything

Those who give up essential liberties for temporary safety deserve neither liberty nor safety
 
 
 
 
    Osmium
(Stoni's sexual toy)
06-01-02 00:13
No 316427
      DME, or Dimethyl Ether (chemical formula: ...  Bookmark   

DME, or Dimethyl Ether (chemical formula: CH3-O-CH3) is a clear colorless, nontoxic environmentally benign compound that is currently used commercially as a propellant for various aerosol products including perfumes, hair spray and other health products.  DME is used in over 10 billion aerosol cans, primarily in Western Europe and North America. 
In the atmosphere, Dimethyl Ether has a half life of one day and quickly decomposes to CO2 and water.  Dimethyl Ether is neither a carcinogen, a teratogen, nor a mutagen.  When it decomposes, it does not lead to formaldehyde formation.

http://www.dmeforpower.net/pg_background.html

I'm not fat just horizontally disproportionate.