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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: robvba on February 21, 2009, 01:06:27 PM

Title: How would you synthesize a benzene with one equivalent deuterium?
Post by: robvba on February 21, 2009, 01:06:27 PM

How would you synthesize a benzene with one equivalent deuterium?
One way i can think of would be to
1. add Br with an Fe catalyst
2. then add Mg
3. then add D2O to displace MgBr
and you should have a benzene with one equivlanet deuterium.

Is there another simple way of adding a deuterium to a benzene?

Title: Re: How would you synthesize a benzene with one equivalent deuterium?
Post by: azmanam on February 21, 2009, 02:07:41 PM

that sounds pretty good to me.

you might be able to do a Bergman Cyclization (http://name.howtochem.com/bergman-cyclization/) where you've exchanged one of the terminal alkyne protons for deuterium (take starting endiyne, deprotonate x1eq base, quench D2O). 

but there's nothing wrong with your route. (except you need Br2 and FeBr3 as reagents step1)

Title: Re: How would you synthesize a benzene with one equivalent deuterium?
Post by: robvba on February 21, 2009, 03:38:41 PM

so using the Bergman cyclization i can
1. treat enediyne with heat or light
2. use tertBuO- to strip an H+
3. add D2O to add one equivalent D

does that sound right?

Title: Re: How would you synthesize a benzene with one equivalent deuterium?
Post by: azmanam on February 21, 2009, 03:47:17 PM

other way around.  1 eq base on the enedyne to deprotonate.  1 eq D2O to add one equiv D.  then heat/light + cyclohexadiene.

Title: Re: How would you synthesize a benzene with one equivalent deuterium?
Post by: robvba on February 21, 2009, 05:01:13 PM

thank you.

what about:

1. add Cl2 + FeCl3 to benzene
2. add 2Li in hexane
3. add D2O

Title: Re: How would you synthesize a benzene with one equivalent deuterium?
Post by: lutesium on February 22, 2009, 08:14:47 AM

Just out of curiosity why do you need that compound???


Lutesium...

Title: Re: How would you synthesize a benzene with one equivalent deuterium?
Post by: robvba on February 22, 2009, 12:31:28 PM

this is for an organic chemisty class and my own understanding. It will not be synthesized in a lab.