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Natural Science Forum / Chemistry / Organic Synthesis / August 2005



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diacetylene magnesium

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iqa965@mail.usask.ca - 16 Aug 2005 13:15 GMT
Does anyone know of or read about diacetylene or diethynyl magnesium
(not commercially available, but the Cas registry number is
111463-03-7). I have searched online and Sci finder about how to make
this reagent and I found one, but not very clear on how to make it
(Bulletin de la Societe Chimique de France 1987 (1),165-73). The only
general method i found was the use of dioxane with few Grignard
reagents to make dialkyl magnesium. (Organometallics, 2001, 20,
1569-1574). Also, does anyone know if making this reagent is explosive
in nature and requires special handling.  I need this reagent for a 1,4
addition reaction because one paper proved that for dimethyl magnesium
in presence of catalytic MgCl, the selectivity of the reaction is
greater than the use of  MeMgCl (J. Am. Chem. Soc. 1990, 112, 9393-4).
I want to try this reaction to see any increase in  yield and/or to
eliminate by-products, but I need to make diacetyleneMgCl.
dave - 22 Aug 2005 09:05 GMT
The mechanium that I am most familuar with for making di aetylene Ca is
to soak the Ca carbide in excess liquid acetylene but I can safely say
that the process is nothing remotely like safe.  A bit more amenable
process would be to go via the nitride or the amide I haven't used
either how ever both process are pretty well knowen.
 
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