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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Kaladiscope on June 19, 2012, 07:48:27 PM

Title: Name of a reaction
Post by: Kaladiscope on June 19, 2012, 07:48:27 PM

Sorry guys,

I would like to ask u how does it call the following reaction:

R¹MgBr + R²-OMs ------> R-²-R1 + MsOMgBr

Is it a Grignard reaction?

Title: Re: Name of a reaction
Post by: discodermolide on June 19, 2012, 11:51:24 PM

Quote from: Kaladiscope on June 19, 2012, 07:48:27 PM

Sorry guys,

I would like to ask u how does it call the following reaction:

R¹MgBr + R²-OMs ------> R-²-R1 + MsOMgBr

Is it a Grignard reaction?

Yes it is a Grignard reaction. It is also a variant of the Wurtz coupling this uses sodium.

Title: Re: Name of a reaction
Post by: Kaladiscope on June 20, 2012, 05:26:17 AM

Thanks!

Do u think that Cadmiun could be better than magnesium in such reaction?

Like forming first the cadmiun derivative:

R-CH2Br + Cd ----> R-CH2CdBr

and then reacted it with for example:

R-OMs + RCH2CdBr -----> R-CH2-R + MsOCdBr

It is mesylate a good leaving group for this case?

Title: Re: Name of a reaction
Post by: sjb on June 20, 2012, 05:29:23 AM

Quote from: Kaladiscope on June 20, 2012, 05:26:17 AM

Thanks!

Do u think that Cadmiun could be better than magnesium in such reaction?

Like forming first the cadmiun derivative:

R-CH2Br + Cd ----> R-CH2CdBr

and then reacted it with for example:

R-OMs + RCH2CdBr -----> R-CH2-R + MsOCdBr

It is mesylate a good leaving group for this case?

Organocadniums are known, see e.g. http://en.wikipedia.org/w/index.php?title=Organocadmium_compound&oldid=493342441. Whether they are better, is diffiicult to say - I would imagine the toxicity may be a key point, both for the metal and the anion equivalent.